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Established in 1691 as a royal port for trade and tax collection, Yorktown, Virginia, reached its economic peak in the mid-1750s, when it boasted shops, taverns, a busy wharf and elegant homes on the bluff. However, the chief local crop was tobacco, which depletes the soil, so the town was likely already remaking itself in 1781 when Lord Charles Cornwallis chose the site as a base for the British fleet. The York River—a tidal estuary of the Chesapeake Bay—has a deep natural channel, making it ideal for maritime maneuvers, even today.

Fortunately for us, General George Washington and Count Rochambeau had daring plans for this riverfront enclave, which hosted the decisive battle of the Colonial revolt—a three-week siege that decimated two-thirds of the hamlet and heralded the final days of the Revolutionary War. Yet this would not be Yorktown’s only brush with disaster: In 1814, a fire destroyed much of the recovering city. And during the Civil War, Union troops inadvertently blew up most of a city block. Thus, Yorktown’s history is one of reinvention. While the town may never recover its original economic prominence, residents cherish its pivotal role in American history and welcome all comers.
“People are passionate about Yorktown’s history and preserving it,” says Amy Demetry, who purchased the Marl Inn Bed & Breakfast with her husband and relocated there from Bowie, Maryland, three years ago. Locals often volunteer at historic sites or participate in the Fifes and Drums of Yorktown, a group of community members who teach music and history and perform in local events.

These days, Yorktown’s white-sand beach is dotted with technicolored umbrellas when the waters are warm. Visitors can stroll the brick Riverwalk Landing and read signs that detail the many peoples who have plied these waters—from the Powhatan tribe to French and British fleets to American submarines based at the Naval Weapons Station just up the river. If you’re lucky, you’ll catch an opening of the 90-foot-high Coleman Bridge, the largest double-swing-span bridge in the U.S., which turns sideways to let vessels upriver.

Best of all, Yorktown offers multiple means—foot, wheels and water—by which to explore this charming landscape. And a trolley (visityorktown.org) that hits all the sights runs daily through November 18 and on Friday, Saturday and Sunday from November 23 through December 30.

Back in Time
The state-of-the-art American Revolution Museum at Yorktown (historyisfun.org) aims to tell all sides of the town’s story. Built in 2017, it boasts an immersive theater that reenacts “The Siege of Yorktown” on a 180-degree screen complete with smoke, smells and rumble seats. Throughout the museum, illustrations, paintings, portraits, moving-shadow projections and even holograms ignite the imagination. Also on display: a model of The Betsy, a British ship commissioned to transport food and supplies that sank nearby. Artifacts on view from the wreck include cuff links, pipe bowls and tiny rat skulls.

Strolling the grounds outside the museum, visitors find re-creations of a Continental encampment, slave quarters and a Colonial-era farm, complete with costumed interpreters and livestock (in season). Replica cannon and musket firings take place at both the museum and the Yorktown Battlefield.

The Yorktown Battlefield and National Park Service Visitors Center (nps.gov/york) sits atop the grounds of Cornwallis’ main defensive position, making it an ideal starting point for a ranger-led, 45-minute Siege Line tour. On a recent tour, park ranger Robbie Smith gave me goosebumps as he recounted the pivotal events of the battle on its actual site. He encouraged us to ponder Washington’s “daring decision” and the “calculated risks” he took in marching 17,000 troops and heavy artillery south to attack the British, with no guarantee that the French fleet would arrive or be successful in driving the British fleet back. He described the Continental Army’s bombardment of Yorktown with siege cannons and the ways Washington found to exploit the uneven, marshy terrain using what Smith termed “classic siege warfare” techniques. He evoked the ordeal British soldiers must have endured while more than 15,000 rounds were fired into their ranks over eight straight days.

After the tour, purchase a CD to guide your drive through the battlefield’s highlights. Be sure to stop by Surrender Field where, on October 19, 1781, British troops paraded in front of a tattered Continental Army and turned over their weapons. Claiming illness, Cornwallis didn’t show up but wrote to King George: “I have the mortification to inform your Excellency that I have been forced to …surrender.” Words to bring a smile to any patriot’s heart, then and always.

Love the musical “Hamilton”? Then don’t miss the short drive to Redoubt #10, an earthen fortification, still partially intact, where Lieutenant Colonel Alexander Hamilton valiantly led his light infantry to overcome one of the last British defenses. This assault, described in the musical, included the 1st Rhode Island Continental Regiment, which was primarily composed of African-American soldiers.

One If By Land…
Looking for a quick way to take in the town? Patriot Tours & Provisions (patriottoursva.com) affords multiple means of exploring, with guides or independently. Their two-hour Segway tour zips along the river landing and up to the bluffs overlooking the river; it includes Grace Church, the Royal Welsh Fusiliers Redoubt and the circa-1730, brick Nelson House, with a cannonball still in its side. The provisioners will also outfit you with your own kayak, bike or paddleboard.

Those coming by water can anchor for hours or overnight at the Riverwalk Landing piers. Both the Schooner Alliance and the Schooner Serenity (sailyorktown.com) offer sails on the river from April through early November, along with an occasional pirate tour.

Delectable Dining
Yorktown dining options lean casual with riffs on the local bounty, including cobia, clams and oysters. Ideal for yummy breakfast and lunch treats, Carrot Tree Kitchens (carrottreekitchens.com) offers a daily crepe special and buttermilk biscuit sandwiches. Looking for a good burger and a brew? Check out the locals’ favorite hangout, the Yorktown Pub (yorktownpub.com). Along with live music on weekends, it also serves up middleneck clams, York River oysters and a local catch.

Waterfront and bridge-view dining options include the Water Street Grille (waterstreetgrille.net), which boasts no-filler crab cakes, local oysters and cucumber wasabi coleslaw. The slightly more formal Riverwalk Restaurant (riverwalkrestaurant.net) features a tasty she-crab soup, along with grilled elk chops and killer fish tacos.

While strolling the sites, get your java fix at Mobjack Bay Coffee Roasters (mobjackbaycoffee.com), located in the cheery, circa-1730 Cole Digges House. Choose from chicory, Southern pecan or Tidewater blends.

Room at the Inn
While larger hotels abound near Williamsburg and Busch Gardens, Yorktown offers three charming inns—all just steps away from historic sites. The Hornsby House Inn (hornsbyhouseinn.com) has rooms in a colonial-style home built in 1933 and furnished with family antiques. Guests can relax on the porch that overlooks the 98-foot-tall, white-granite Yorktown Victory Monument.

Named after a Colonial-era building material, the Marl Inn (marlinnbandb.com) is a colonial-style house with beautifully landscaped gardens and a patio. The scrumptious breakfast at the York River Inn (yorkriverinn.com) overlooking the waterfront may include ham and feta pie or poached pears with cranberries.

Arts, Crafts and More
Pop into Viccellio Goldsmith & Fine Jewelry (viccelliogoldsmith.com) to catch the owner crafting some of his original designs, and even commission your own creation. Auntie M’s American Cottage (auntiemsamericancottage.com) focuses on made-in-America crafts, folk art and cards. The owner of Redcoat Antiques (757-890-1409) clearly has a sense of humor. Located in a traditional home, this shop offers jewelry, furnishings and paintings collected by its well-travelled British owner.

The Yorktown Onion (757-872-8232) showcases eclectic jewelry and home goods. The image of a Yorktown onion—a local plant with a purple flower—graces much of the artwork hereabouts. On the Hill Gallery (onthehillgallery.com) is an artists’ cooperative showcasing pottery, paintings and sculpture. A wide array of crafts, paintings and knickknacks is available at the Gallery at York Hall (visityorktown.org), which also serves as a local information center.

The American Revolution Museum shop proffers Colonial craft kits, maps, T-shirts and the de rigeur tricorn hats. Its book section includes an excellent children’s selection, with the Colonial story told from every perspective. The battlefield visitors center has reproductions of Colonial-era glassware, books and puzzles. And you can find a colorful collection of kites, yard flags and sun hats at Patriot Tours & Provisions.

Festivities
Make time for Market Days at Riverfront Landing, which take place November 10 and 17 and December 8; participants in these popular events enjoy a farmers’ market, vendors, artwork and live music. Yorktown also hosts a Christmas Market and Lighted Boat Parade on December 1. For more information, see visityorktown.org.

All photos courtesy of Yorktown Tourism.

Street Art An enormous, abstracted fox leaps across one building. A stylized girl enigmatically dangles a key in one hand and an open-mouthed metal fish in another. These are just two of the 12 colorful, often surreal murals that now adorn otherwise bland buildings in the 10-block area of the Annapolis Design District—home to design showrooms, consignment shops, and car dealerships.

The murals happened “a little bit by accident and a little bit by destiny,” says Severna Park resident Roberta Pardo, the driving force behind Urban Walls Brazil (UWB), which has imported street artists to paint and lead workshops for children since 2014.

Pardo—a Brazilian-born artist who studied in Brazil and California—was already active in the local arts scene, serving on the board of the Arts Council of Anne Arundel County when she was approached to co-curate an exhibit of Brazilian artists at George Washington University. That exhibit’s success inspired her to create UWB, an arts residency program that brings international street artists to Annapolis. The Design District buildings provide ideal canvases for murals, which are created with spray paint, stencils and rollers. Once denigrated as “graffiti,” street art is now an acknowledged art form that transforms urban spaces worldwide.

“Coming from Brazil, I’ve seen the power of art when used as a tool of communication,” says Pardo, who speaks six languages. “Street art is really giving a voice to the people. I try to bring different styles, different stories.” She keeps up with artists on Instagram; with her artistic eye, she looks at a wall and knows exactly which artist will suit the space.

Meanwhile, the Annapolis community has embraced her vision. Each September, the Art in Action—Fall Street Festival celebrates new murals. After watching the process and getting to know the artists, the locals feel pride and ownership in these works of art, notes Pardo, who has her eye on street artists from Mexico and Uruguay this year.

“The murals have created a buzz about the Design District,” says Susan Seifried, vice president of public relations at Visit Annapolis, who’s seen international interest in the street art.

UWB is largely a one-woman show, with Pardo scheduling, transporting and housing the artists. A mother of three, she’s also passionate about bringing artists into schools to share their culture and vision. “The murals are there to be enjoyed, but they’re also there to raise questions,” she says. “For people to understand and to see that there are different ways to see beauty in things.” urbanwallsbrazil.com

Up-and-Coming Rock HallGeography has long shaped the destiny of Rock Hall, nicknamed “the pearl of the Chesapeake” and located on Maryland’s upper Eastern Shore. Less than two hours from many urban centers, Rock Hall has long been a point of transit for both goods and people on their way to somewhere else. In colonial times, a popular ferry between the Eastern Shore and Annapolis departed from Rock Hall, and both George Washington and Thomas Jefferson passed through town on journeys to Philadelphia to attend the Continental Congress. A small stretch of beach known as Ferry Park remains a popular place to plunge into the bay or catch a splendid sunset.

An ideal spot from which to harvest the bay’s riches, Rock Hall once boasted a vibrant fishing industry. Commercial watermen still ply the waters from the harbor, but their numbers have dwindled along with the oyster, crab, and rockfish catches. However, pleasure boating is picking up the slack, and with 12 marinas in town, Rock Hall is said to have as many boat slips as full-time residents.

Popular among boaters who make the easy trip from Delaware and Philadelphia to winter and repair their boats, Rock Hall’s friendly and unpretentious charms are less well-known in the DC region. But the secret is out—and this once-hidden getaway now finds itself on the map. However, with only one flashing traffic light on Main Street, the town retains its old-timey feel and encourages visitors to unplug.

For a glimpse of yesteryear, pop into the Waterman’s Museum, a small house featuring such relics as photos, an old crabbing boat and traps, and a life-sized diorama of a waterman in bed, his loyal (stuffed) dog at his side. Rent a bike at Rock Hall Landing (rockhalllanding.com) or one of the other marinas to explore both the winding waterfront and the town.

On the Water
True to its heritage, the town abounds with fishing guides and day charters to help you land the big one (rockhallmd.com/business-directory/by-category/Fishing-Charters-&-Hunting-Guides). If you prefer lovely vistas and the wind in your hair, sail aboard the 43-foot yacht “Island Girl,” captained by Mark Einstein of Blue Crab Chesapeake Charters (bluecrabcharters.com). A 90-minute cruise is offered five times daily in season. To explore the shoreline more intimately, rent a kayak or paddleboard from Chester River Kayak (crkayakadventures.com) or take their half- or whole-day guided trips. Looking to make a romantic splash? Both yacht and kayaks offer sunset cruises.

Eight miles from town, the 2,285-acre Eastern Neck National Wildlife Refuge (fws.gov/refuge/Eastern_Neck) is home to 70-plus nesting birds to check off your wish list, including osprey, bald eagles, nuthatches and tundra swans (in the winter). Seven trails, observation platforms, and a visitor’s center help nature lovers interact with the refuge, which offers brackish marshes, ponds, upland forest and grassland habitats. Or test your own crabbing skills where the Chester River meets the bay. Eastern Neck Boat Rental (eastneckboatrental.com) provides everything you’ll need from a boat to baskets, bait, and nets. You can take home up to a bushel of blue claw crabs.

Delectable Dining
Dating back to 1872, Durding’s Store (410-778-7957) preserves local traditions with sodas and floats made the old-fashioned way and served beneath an original tin ceiling. Crowd pleasers include milkshakes, fresh-roasted turkey sandwiches, and crab soup. Billing itself as a coffeehouse/café/wine-and-gift emporium, Java Rock (javarockcoffeehouse.com) offers everything from lattes and wine to greeting cards and felt hats. Check out their array of colorful socks and hot mitts with attitude, and enjoy the ample outdoor deck. Bay Wolf (baywolfrestaurant.com) serves up a mix of Austrian food and bay specialties from Weiner schnitzel and apple strudel to oyster stew and clams casino.

For waterside dining and sunsets over the water, pull your boat or car up to Waterman’s Crab House & Dock Bar (watermanscrabhouse.com) to feast on steamed little-neck clams, baked crab imperial and ribs. On summer weekends, this indoor/outdoor venue features live music ranging from local acts to steel-drum bands. Or kick back and eat with the locals at Harbor Shack (harborshack.net), which dishes up both seafood and Mexican specialties and also offers harbor-side dining, boat slips, and live music. The funky and casual Mainstay Theater (mainstayrockhall.org) showcases both local and national musical acts in a café setting where you can bring your own dinner and buy drinks.

Eclectic Wares
Hickory Stick owner Sandy Scott refers to her store (thehickorystickrockhall.com) as “the Neiman Marcus of Rock Hall” because it boasts various “departments,” including home furnishings, tea, sunhats, jewelry, and apparel. Most items have a maritime or beachy theme, but you’ll also find Vera Bradley and other boutique purses. Check out the hip and colorful distressed furniture made of retired teak boats from Bali. At Smilin’ Jakes (smilinjakescasualapparel.com), choose from a bright selection of island wear—think aloha shirts and floral dresses—to outfit any Parrothead (aka Jimmy Buffet fan).

The owner of Vintage Picnic (vintagepicnic.biz), Susan Gates, likens her shop to a Build-A-Bear workshop that upcycles older finds to make a memorable picnic. Shoppers bring in legacy pieces—heirloom linens, Limoges plates, crystal stemware—that are incorporated into lined baskets that make ideal wedding gifts. Find traditional antiques, oriental rugs and random finds at sister store Vintage Home. “We’re trying to make antiques interesting for the next generation,” says Gates. “We love to talk to people about how to use pieces.”

Housed in a former wood-frame abode, Swan Creek Gallery (swancreekgallerymd.com) specializes in nautical watercolors, photography and whimsical painted-driftwood fish, and is open summer weekends only or by appointment. Village Quilting (facebook.com/Village-Quilting-LLC-717472545049118) features maritime-themed fabrics with crabs, whales, sailboats, and lobsters, so you can stock up for any long voyage. They also offer quilting classes and a long-arm quilting service.

With its cluster of tiny, colorful incubator shops, Rock Hall village boasts a variety of wares and treats. At Sweet Cheeks (sweetcheekscookies.com), choose from iced cookies, candies, homemade donuts and seasonally-themed treats. Get the Scoop (facebook.com/getthescoop104) serves locally-sourced Kilby ice cream with flavors like hibiscus and the kid-favorite Cookie Monster.

Cozy Accommodations
Whether coming by land or sea, you’ll find a welcome berth for both boat and body at several local inns. Built-in 1993 in Colonial Williamsburg style, Osprey Point Inn, Restaurant and Marina (ospreypoint.com) combines a historic vibe with modern conveniences on 30 waterside acres. The inn features reclaimed-wood floors and four-poster beds, while the marina offers 160 slips. Serving dinner Wednesday through Sunday and Sunday brunch in season, the restaurant features seafood specialties from fried oysters with lemon Old Bay aioli to crab-crusted scallops in lemon-garlic butter. A pool, bikes, kayaks, paddleboards and a cozy bar are also available.

Choose from single rooms, cottages or a whole house at the Inn at Haven Harbour (havenharbour.com), which boasts two pools; a seasonal bar and grill; kayaks, bikes and lawn activities. Many of the bright, nautically-themed rooms spill onto small, private decks overlooking Swan Creek. The marina has 200 boat slips, plus another 150 at the New Haven Harbor South.

For a secluded getaway between Rock Hall and the wildlife refuge, meander over to the Inn at Huntingfield (huntingfield.com) where accommodations range from rooms in the elegant Manor House to private cottages that allow visitors to disconnect in luxury. A pond, a pool, fields of sunflowers and lavender, woods and a tranquil creek enliven the property’s 70 acres. The full breakfast may include berry bread pudding with blackberries grown onsite. Some cottages are pet-friendly.

Rockin’ Festivals
From triathlons (June 2-3; vtsmts.com/rockhall) to log canoe regattas (July 14-15; rockhallyachtclub.org), Rock Hall celebrates water-based events all season long. From mid-May through September, the town hosts Festive Fridays from 6 to 8 pm each weekend. Catch live music at both ends of Main Street and sample sidewalk sales and treats. The town’s annual Fourth of July celebration is considered one of the best on the bay with impressive fireworks over the harbor on July 3rd and an old-fashioned, small-town parade the next day with flags a-flying.

Unleash your swashbuckling side at Pirates and Wenches Fantasy Weekend (rockhallpirates.com). Celebrating its 11th year, this popular, town-wide costume festival welcomes pirate re-enactors and musicians and includes a decorated dinghy contest, fun run, rum tasting, sea-shanty sing-a-long and Caribbean-style beach party. Vintage-car lovers should check out Cruise Night every third Friday during the summer months; this festive event closes down Main Street so aficionados can admire the stylish jalopies and enjoy a DJ spinning oldies.

Harbor City From its beginnings in 1649 as a Puritan community on the Severn River to its present status as an international sailing mecca, Annapolis has been welcoming guests for centuries. The town boasts an array of seasonal activities, shops, and history—much of it revolving around the riches of the river and the nearby Chesapeake Bay.

With a cornucopia of American architectural styles, Annapolis is commonly called a “museum without walls.” Color-coded, octagonal markers help visitors find 240 well-preserved, historic structures across the city. For example, red means Georgian (1715-1800) while yellow highlights distinctive early 20th-century styles, from Beaux Arts to Craftsman.

To get the lay of the circles, streets, and waterways, head first to the Visitors Center for an acclimating tour of the city by trolley or five-passenger electric vehicle. Two central circles mark the oldest section of Annapolis: State Circle surrounds the circa-1772 Maryland State House, which once served as our nation’s capitol building and is in legislative use today. Located in Church Circle, St. Anne’s Church dates back to 1858. From these circles, Annapolis divides into roughly five scrollable main areas, each of which will tickle both your fancy and your taste buds.

CITY DOCK/MAIN STREET
For the busiest and most touristy part of town—and views of the harbor—follow Main Street toward City Dock, which overlooks Ego Alley. This narrow strip of water offers boat owners a chance to strut their stuff for the crowds at surrounding coffee shops and restaurants, provided they don’t get themselves stuck navigating the maritime traffic. No boat? Set sail with the Woodwind or Woodwind II, 74-foot staysail schooners that offer two-hour sails in the bay and around the Naval Academy, and overnight stays in the warmer months.

The poignant Kunta Kinte/Alex Haley memorial commemorates the spot wherein 1787, Kunta Kinte and 97 other slaves debarked in Annapolis Harbor from the ship Lord Ligonier. The memorial depicts a life-sized bronze statue of Haley reading to a group of children and points toward the Chesapeake Bay—the road his ancestor traveled to get here. Visitors can also read excerpts from Haley’s influential novel, Roots, and more, on 10 markers along Compromise Street. The site hosts an annual Kunta Kinte Heritage Festival in September with live music, food, and vendors.

An Annapolis institution, the always-hopping Chick and Ruth’s Delly makes its own donuts, along with colossal shakes, crab eggs Benedict and an array of Maryland politician-themed sandwiches. At Preserve, husband-and-wife Culinary Institute of America grads Jeremy and Michelle Hoffman celebrate pickled and fermented foods with offerings from a glazed beef rice bowl to house-made specialty pickles. Drop by for happy hour specials to pique your palate. Overlooking the dock, Iron Roosters serves breakfast all day, along with house-made pop tarts.

Shopping in this area of Annapolis ranges from nautically themed Sperry shoes to fashions by Lily Pulitzer. Want to immortalize your own piece of the shoreline? Head into Nautical North for custom wall charts and gorgeous 3-D maps of your favorite property or body of water. And from November 25 to December 17, take advantage of local artisans displaying their wares, from art and jewelry to gifts and holiday décor, at the Here A Pop-Up Shop at 186 Main Street.

Centrally located lodgings offer walking access to the sites and a chance to sleep in historic digs. Gibson’s Lodgings offers a Georgian main mansion, plus two other 19th century-themed homes and a breakfast that includes a waffle station. Historic Inns of Annapolis features three history-rich homes with Victorian flair on or near State Circle.

Not far from City Dock, the U.S. Naval Academy is open for walking tours of its impressive campus on prime waterfront real estate. Its domed main chapel houses four gorgeous Tiffany windows and the stunning marble crypt belonging to John Paul Jones, known as the father of the U.S. Navy. For something truly unusual, take a few minutes to wonder at the intricate, otherworldly sculptures of ships carved out of bone by French prisoners during the Napoleonic Wars, on view in the Naval Academy Museum.

For those who can’t get enough of Annapolis’s varied architecture, a two-hour, local architect-led tour of the city, ArchiTrex
highlights the most notable historic buildings; tours run the second and fourth Saturdays from City Dock, May through September. The Annapolis Yacht Club hosts sailboat races every Wednesday night from late April through August. More than 100 crews vie for weekly honors.

MARYLAND AVENUE
This charming, bustling street, which stretches northeast from State Circle, is a must-see destination for anyone interested in home design. Its eclectic community of designers and their shops offers myriad visions for your home, from nautical to vintage to traditional.

Lured by affordable finds? Evergreen Antiques and True Vintage will set your heart aflutter with its furnishings and clothes. Try sunny, airy Be Home for that perfect accent pillow or light fixture, and if cottage chic floats your boat, check out the furniture, gifts, and accessories at A Touch of Fancy. If your taste trends toward repurposed and vintage furnishings, Barefoot Dwelling’s (barefootdwelling.com) unique finds and inventive ideas will make you smile. Don’t miss Natalie Silitch for handpicked antiques and whimsical, one-of-a-kind pieces that don’t stay long in her shop, including water-themed wall art and stuffed mermaids.

Serve your own spread of the Chesapeake’s bounty in a nautically themed platter or bowl from The Annapolis Pottery right on State Circle. Old Fox Books & Coffeehouse is the place to pick up a great read or enjoy a conversation over coffee. If the weather’s nice, hang out with the handsome suit of armor on its inviting deck.

THE DESIGN DISTRICT
Keep walking out West Street from the circles and you’ll hit the Annapolis Design District, an eclectic, up-and-coming neighborhood with an industrial mix of car dealerships, consignment stores, and home-design showrooms. Design junkies will love letting their imaginations wander through the latest innovations at large showrooms such as Kitchen Encounters, proffering a range of cabinetry options plus design services, and Walterworks Hardware. In Home Stone offers shoppers two full-service showrooms featuring a tantalizing array of tile and granite.

The Design District boasts 12 colorful, eye-catching murals created by street artists with Urban Walls Brazil over the last two years to beautify this grittier area. The annual Art in Action—Fall Street Festival celebrated the murals’ unveiling in September.

WEST STREET
Dubbed the Arts and Entertainment District of Annapolis, West Street fans westward from Church Circle. Catch a show at Ram’s Head On Stage; the coming line-up includes eclectic acts, from the jazzy strains of the Stanley Clarke Band to Judy Collins’s soulful crooning to Jim Belushi’s comedy. The Annapolis Shakespeare Company performs works of the Bard and other masters on the main stage and in a smaller black box theater.

In the spirit of European cafés, 49 West Coffeehouse, Winebar & Gallery epitomizes the artsy mix of food, wine, and conversation to which this section of Annapolis aspires. When the cold sets in, satiate your craving for sweets at the Annapolis Chocolate Binge Festival on December 3rd at the intersection of West and Calvert Streets.

Farther up the way, Sailor Oyster Bar specializes in oysters and craft cocktails in a casual, industrial setting. Featured on “Diners, Drive-Ins and Dives,” Miss Shirley’s Café will make you a morning cocktail (a mimosa, sangria or their own spicy Bloody Mary) and fill you up with their Southern skillet or chicken ’n waffles (open only through lunch). Drop into the hip and happening Ceremony Coffee Roasters for a needed jolt of energy.

Galleries abound as you walk this neighborhood. The Annapolis Collection Gallery focuses on the paintings and photography of seven Annapolitan masters, with an array of styles from historical recreations to Asian brush painting. Pop into painter Nancy Hammond’s colorful studio to check out her annual Annapolis poster.

Overnight visitors who prefer larger venues will enjoy O’Callaghan’s Irish ambiance or Loews’ modern conveniences.

EASTPORT
For a funky, independent vibe, follow Compromise Street across the bridge at Spa Creek and into an area dubbed “the Maritime Republic of Eastport” in 1998, when the bridge to Annapolis was closed and Eastport “seceded.” Since this tongue-in-cheek incident, the bridge has reopened, but many locals still fly a flag commemorating that event. Or, you can take the water taxi from City Dock to arrive in style, May through Labor Day.

Despite its smaller size, Eastport offers a host of superb dining options. Head to Lewnes Steak House for hearty meats in a traditional, chop-house setting. Craving that perfect crab cake? Boatyard Bar & Grill is a hopping spot for crab and other local delicacies. Located in one of Eastport’s many Craftsman-style homes, Vin 909 never disappoints with its organic farm-to-table focus and fine wines. Sample the wild boar meatballs, local sea scallops or brick oven pizza.

Living up to its description as quirky, Eastport hosts several outside-the-box events each year. You can test your—ahem—skills at the annual .05 K race across Spa Creek Bridge. (Yes, you read that right.) Or cheer residents on during the annual tug-of-war contest with the other side of Annapolis, which spans the width of the river each year. The Eastport Yacht Club Lights Parade, which won a USA Today reader’s choice award for Best Holiday Parade last year, will again illuminate the waters on December 9.

Other Eastport activities to note: The Annapolis Maritime Museum hosts an annual Annapolis Oyster Roast & Sock Burning to mark the Spring Equinox and celebrate the opening of boating season when socks become superfluous. The 2018 festivities on March 24 will feature live music, an oyster-shucking contest and oysters served in myriad styles. Feeling adventurous? Tour the city by water at night on a LED-illuminated paddleboard tour that leaves from Eastport, of course.

Amy Brecount White launches her search for nautical views and delicacies from Arlington, Virginia. Photos courtesy of visitannapolis.org.

Stand anywhere in Oxford and you’ll likely find yourself peering through a cluster of sailboat masts toward peaceful waters beyond. The heart of this quaint village with shipyards and marinas galore rests on a peninsula jutting into the Tred Avon River, due south of St. Michaels on Maryland’s Eastern Shore.

“We have more boats than people!” says Judy Bixler, who for the past 30 years has co-captained (with husband, Tom) the historic Oxford-Bellevue Ferry (oxfordbellevueferry.com)—the lifeblood of this town at the end of the road. Established in 1683 (as was Oxford itself), the ferry is a favorite of both road trippers and cyclists making a loop through St. Michaels and Easton. Crossing the river from 9 a.m. to sunset every 15 to 20 minutes from April through October (and weekends in November), it offers one means of parting the local waters.

Oxford’s proximity to the Chesapeake Bay made it an official port of entry during the colonial era when it was a center for international shipping and the local tobacco trade. Another heyday came at the waning of the 19th century when trains, steamships, and the local oyster industry still boomed. However, over the years the pace of life in this village has slowed to what locals refer to as “Oxford time.” To trace the town’s ebb and flow through the last three centuries, drop by the Oxford Museum (oxfordmuseum.org), open from April 22 through the fall.

With a brand new public boat landing and several new businesses welcoming visitors this spring, this hamlet of watermen, families, and retirees is experiencing a quiet renaissance. Now is the perfect time to stroll Oxford’s brick sidewalks and admire its bright frame homes where rocking chairs and flags festoon the front porches. As Ben Sheets, a local resident and the co-owner of Capsize (capsizeoxmd.com), a new waterfront restaurant scheduled to open in late April, describes it, “Oxford is as close to a Norman Rockwell town as you can get.”

Old-Fashioned Festivities  Not surprisingly, most of Oxford’s special events celebrate the surrounding waters and local history. Oxford Day on April 22 features an old-fashioned parade, live music, vendors and local cuisine. For something entirely different, head to town on June 24 for the cardboard boat races. Or watch the fascinating and historic log canoe races during the Oxford Regatta on August 12 and 13.

Want to own a piece of Oxford? Every spring, local artists paint sections of picket fences to celebrate the town’s idyllic qualities. Their work is displayed in town throughout the summer, then sold to the highest bidders at the annual Picket Fence Auction on October 7, with proceeds benefiting the artist’s charity of choice.

Call of the Water  Those arriving in Oxford by water will find ample slips for tying up boats. Or rent your vessel of choice at Dockside Boat Rentals (docksideboatrentals.com), which offers inflatables, wave runners and powerboats as well as kayaks, paddle boards—and bicycles for landlubbers.

To spy the yacht of your dreams, visit the elegant Cutts & Case Shipyard (cuttsandcase.com), which harkens back to the days of classic wooden boats and superb craftsmanship. And on Friday evenings from May through September, cheer on sailboats competing in these inviting waters during the Oxford Amateur Racing Series.

Clues and Sundries  Oxford’s zoning laws keep the commercial district small, but the shops that call the town home are gems. The figure of a fierce dragon guards the eclectic treasures at Americana Antiques (americanaantiques.net), which specializes in furniture, folk art, and vintage carousel animals; take a gander at the miniature portraits, vintage political buttons, and maritime landscapes. Across the way, the newly opened Yacht and Home (yachtandhomeoxford.com) showcases sunny accent pieces—pillows, rugs and local art—to personalize your home or boat. Here you can shop for resort apparel, designer doorknockers, gifts and nautical finds.

And don’t miss the comfy bookstore Mystery Loves Company (mysterylovescompany.com), located in a former bank. Complete with an open vault stocked with books, it’s owned by a former librarian who, upon hearing your predilections, matches you with a mystery. The store also specializes in local authors and Chesapeake-related reads.

Mouth-Watering Menus  For a teeny town, Oxford offers an array of dining options to set a foodie’s heart aflutter. When master chef Mark Salter and his partner, Ian Fleming, (both formerly of the Inn at Perry Cabin) refurbished and reopened the Robert Morris Inn (robertmorrisinn.com) in 2010, they put Oxford on the map as a dining destination. Salter’s emphasis on seasonal and locally sourced ingredients keeps the menu fresh and varied, and the inn offers to dine both indoors and out. Mark your calendar for Salter’s delightful cooking demonstrations and themed dinners with music, comedy or wine pairings throughout the year.

With 30 slips available to those coming by boat, Capsize will capitalize on its waterfront setting by offering deck seating for 130—including on lounge chairs. Diners can relax under the awning sails and bring Fido along (hush puppies served daily.) Chef Doug Kirby —who also oversees Easton’s Washington Street Pub—will serve locally sourced fare, such as softshell crab tacos with wasabi and watermelon salsa. Also slated to open in late April, Doc’s Sunset Grill will welcome guests to watch the evening colors shimmer on the water as they dine. And Latitude 38 (latitude38.biz) features an outdoor patio and creative delights such as hazelnut-infused profiteroles.

Oxford’s Town Park, with its sandy beach, play equipment, and tables in the shade, provides a tranquil setting for picnics and watching the world float by. Pope’s Tavern at the Oxford Inn recently opened Pope’s Pantry (oxfordinn.net) for gourmet carryout. And On the Park, a cafe envisioned by Yacht and Home’s owners as the town gathering spot is scheduled to open Memorial Day serving trendy nitro teas and sustainably grown coffees, along with light lunches, tapas, and desserts.

With its award-winning gelato-style ice creams and sorbets, Scottish Highland Creamery (scottishhighlandcreamery.com) alone is worth the trip. Its 600 flavors include sugar-free and gluten-free options—and even Old Bay sorbet.

Landlubber Lodgings  Ideal for nature buffs or couples seeking quiet romance, the Combsberry Inn (combsberryinn.com) boasts a secluded setting outside of town. Guests can stay in the stately manor house or have a charming cottage all to themselves. Hoping to ditch your car in favor of walking, paddling or biking? Then Sandaway Waterfront Lodging (sandaway.com) is ideal. With a sandy beach complete with Adirondack chairs facing the sunset, this tranquil spot is minutes from the town’s attractions and includes a continental breakfast delivered in a basket to your door.

The 1710 Robert Morris Inn (robertmorrisinn.com) supplies a more social and historic setting with mostly tech-free rooms and a complete Maryland breakfast. Within these walls, George Washington likely raised a glass with the wealthy financier, Robert Morris, and writer James Michener also outlined his novel Chesapeake here. If you want a nightcap, you’ll find a warm welcome in its brick and timber-beamed  Salter’s Tavern. The circa-1880 Oxford Inn(oxfordinn.net) also offers seven cozy rooms above Pope’s Tavern and its own porch with rocking chairs.

Amy Brecount White launches her search for nautical views and delicacies from Arlington, Virginia.

Time Traveling in Chestertown Strolling the streets of Chestertown is a little like traveling back in time. A visitor might be in the midst of ordering a cranberry-orange scone with her latte when suddenly the tall ship Sultana glides into port from the peaceful Chester River, conjuring a long-ago vista. The seat of local government since 1706, Chestertown—also known as “America’s best-preserved Colonial seaport”—embraces history and the passage of time in all its rich complexity.

In fact, the Sultana—a replica of a British Royal Navy vessel that enforced those nasty tea taxes during revolutionary times—helped launch this small town into the 21st century. Since the ship’s construction was completed in 2001, educators and tourists alike have flocked to Chestertown to sail on the “Schoolship of the Chesapeake,” learn about the bay’s marine treasures and relive its history. The Sultana is also a centerpiece for the town’s many festivals. If this ship or other vessels are in port when you go, a sail on one of them will show you the town and its environs from the water. Many rural views from this Chesapeake tributary are virtually unchanged since the 1800s, and it’s great fun to peek into the backyards of the lovely waterfront homes. The Chester River Packet Company (chesterriverpacketco.com) also offers day and evening cruises on a 1920s-style tour boat.

Historic Highlights  History buffs won’t want to miss a 30-minute audio tour of the town’s waterfront area researched by scholars, performed by students from local Washington College and available via headphones at the 1746 Custom House. The self-guided tour features riveting personal stories of soldiers, slaves, and revolutionaries—including Thomas Ringgold, a wealthy slave trader and “Son of Liberty” whose house is one of the stops.

A leisurely amble through town will also yield architectural and horticultural delights. Pick up a walking-tour map that will guide you past 24 mostly Colonial gems in mint condition, from the red-brick Geddes-Piper House (home of the Kent County Historical Society and its exhibits) to the 1733 White Swan Tavern, which may have hosted George Washington and is now a bed & breakfast. Washington College, to which George gave his name and some founding funds, abuts the town and is worth a meander for its scenic buildings and landscaping.

Festival Fun  Fall is a festival season in Chestertown. Downrigging Weekend (October 28 through 30; sultanaeducation.org), features historic boats ranging from the pristine tall ship Kalmar Nyckel (a replica of a Swedish Colonial ship) to adorable wooden Beetle Cat sailboats. Many of the gorgeous crafts in the harbor are available for touring, and visitors can take a spin on tall ships including Sultana, Kalmar Nyckel, The Pride of Baltimore (a Baltimore clipper) and several oyster-dredging skipjacks. The festival also spotlights live music, nautical book talks, and fireworks.

To coincide with Downrigging Weekend, the Chestertown RiverArts Studio Tour (October 22, 23, 28 and 29; chestertownriverarts.org) welcomes art lovers into more than 50 artisans’ studios across Kent and Queen Anne Counties. Pop into the Chestertown RiverArts Gallery to plan your tour while browsing each artist’s work, from paintings to jewelry to vases, on display there. For those planning a springtime visit, Chestertown reenacts its own version of the Boston Tea Party every Memorial Day weekend.

Arts Scene  But, if you’re not in town for a festival, try to make Chestertown’s First Friday event from 5 to 8 p.m. on the first Friday of each month, when shops, restaurants, and galleries offer nibbles and special deals to visitors.

The elegant Carla Massoni Gallery (massoniart.com) showcases paintings, sculpture and woodcuts by highly regarded national artists; the nautical paintings of local favorite Marc Castelli and the works of contemporary realist Greg Mort can be found in the collection. Or visit Hegland Glass Studio (heglandglass.com), where husband-and-wife team Dave and Patti Hegland create kiln-formed art glass with intricate swirls of color and texture. The new, collaborative gallery, Create (createartcraftdesign.com), showcases the Heglands’ work, along with other fine crafts by a metalworker, a fine-furniture maker, a potter and a textile artist. Curated by Carla Massoni, these varied works are selected to complement each other. The artists can be commissioned to create pieces for public and private spaces.

Blue Canary Letterpress (bluecanarypress.com) features work by local and emerging artists along with unique cards, prints and custom designs by second-generation printer Jodi Bortz. And check out the studio of independent publisher Idiots’ Books (idiotsbooks.com), which offers quirky, satirical illustrated titles for adults and a line of children’s books. For musical performances and theater, visit the casual and intimate Art Deco Garfield Center for the Arts (garfieldcenter.org).

Fodder for Foodies  Whether you prefer coffee and a croissant at Evergrain Bread Company (evergrainbreadco.com) or local baked goods and produce from the Chestertown Farmers’ & Artisans’ Market (Saturday mornings, mid-March through December; chestertownfarmersmarket.net), you will not go hungry here. The bright and friendly Lemon Leaf Café (thellcafe.com) serves up everything from flannel cakes with homemade apricot syrup to an assortment of crab entrées. The White Swan Tavern (whiteswantavern.com) offers a traditional tea from 3 to 5 p.m. daily. And the newly renovated Kitchen at the Imperial (imperialchestertown.com ) boasts an all-you-can-eat brunch buffet with a fun build-your-own Bloody Mary and mimosa bar on Sundays.

To further titillate your taste buds, drop by Chester River Wine & Cheese Co. (chesterrivergourmet.com) for a glass (or bottle) of fine wine and an impressive cheese, olive or antipasto board.

Memorable Lodgings   If your idea of a holiday means stashing the car keys, central Chestertown has no shortage of options for accommodations from which you can walk everywhere you’ll want to go. The Widow’s Walk Inn B & B (widowswalkinn.com) and the John L. Stam House (jlstamhouse.com) are Victorian gems in the middle of town that offer full breakfasts and relaxing porches from which to watch the world go by. If driving appeals, the Brampton Bed and Breakfast Inn (bramptoninn.com) a mile outside town boasts private cottages and wood-burning fireplaces in many rooms. You’ll also enjoy a full breakfast, freshly baked cookies, and afternoon tea.

Finally, Great Oak Manor (greatoakmd.com) in Chestertown offers a waterfront experience that is both elegant and active, with kayaks and paddleboards available onsite. At this inn, you’ll enjoy a lovely view of the bay with your full breakfast and complimentary sherry or port to punctuate your evening.

Amy Brecount White explores the nooks and waterways of the world from her base in Arlington, Virginia. 

Escapes Festive & Artsy Easton Easton has long been a gathering spot for a cornucopia of people—from the Quakers who built a meeting house there in 1682 to the art aficionados who now flock to its annual plein-air painting festival. Standing before its impressive Federal-style Talbot County Courthouse, visitors will see both a monument to the “Talbot Boys” who fought for the Confederacy and a statue honoring Frederick Douglass, who was jailed here for a few years before he escaped slavery in 1838. Both the town’s statues and its well-preserved architectural relics attest to the variety of minds and tastes that have called this spot home.

While Easton has long been a seat of commerce and government, the locals also celebrate leisurely pursuits, particularly in the arts and the sport of hunting. The fingers of the Tred Avon River just touch its borders, so there’s no real waterfront in the main town. Instead, visitors will find strollable brick sidewalks and a preponderance of Federal architecture, mixed with some well-preserved Victorian and Neoclassical structures to entertain the eye. Easton exudes stately charm and respectability, but it has a playful side too.

HISTORIC MEANDERINGS  The Welcome Center on S. Harrison Street offers a detailed map for three self-guided walking tours highlighting the town’s local treasures. The Third Haven Friends Meeting House (1682) is the oldest documented building in the state; Quakers gather in its serene interior, open to the public daily. The county courthouse still occupies the site of the original brick courthouse and jail, built by colonists in 1710. Parts of the current courthouse date back to 1794. Housed nearby in the Mary Jenkins House, an early frame structure, the Talbot Historical Society features an interactive display that reveals how local waters and land have controlled the rhythm and growth of the area.

On your wanderings, pop into the lovely Academy Art Museum, located in an 1820 Schoolhouse (academyartmuseum.org), which showcases regional artists along with a fine permanent collection. Savor a sweet treat at Hill’s Drug Store, which boasts an old-fashioned soda fountain. Overnighters can also catch nationally known comedians and musicians at the charming Art Deco Avalon Theatre (tickets.avalontheatre.com).

FUN FESTIVALS  As the largest juried plein-air painting competition in the country, Plein Air Easton (pleinaireaston.com) puts this city on the map. During the 2016 event, 58 local and far-flung artists will paint outdoors all over Talbot County from July 9 through 17.  A favorite is the “Quick Draw” event, a two-hour paint-off when visitors can watch 200 artists in action and then buy paintings they fancy. With a block-party feel, the event also offers workshops, demonstrations and a bustling artisans market.

For a bird’s eye view of the region’s winding waterways, mark your calendar for the Great Chesapeake Balloon Festival (greatchesapeakeballoonfestival.com). Held this year on August 5 and 6 at the Triple Creek Winery, the event offers tethered balloon rides rising 60 feet up, passenger balloon flights over the county and a stunning balloon “glow” with 15 hot-air balloons illuminated and afloat after dark.

Located on the migratory bird flyway, Easton becomes a mecca for the hunting community each autumn during the Waterfowl Festival (waterfowlfestival.org), taking place this year from November 11 to 13. This celebration of Eastern Shore traditions includes everything from retriever demonstrations to superb wildlife art to wine tasting. Over the last four decades, the festival has also raised millions for Chesapeake watershed habitat restoration, education and research.

ABUNDANT ARTS  With art galleries at nearly every turn—there are eight official galleries and lots of other shops featuring art work—you’re sure to find a piece that suits your palate. Owned by two artists, Troika Gallery (troikagallery.com) offers year-round events and a chance to see the owners at the easel or chat them up about the 30-plus artists whose work they show.

“Easton is an incredibly creative town,” says local artist David Grafton, whose landscapes are collected by National Gallery of Art curator Earl Powell, III. Grafton owns a working and teaching gallery, Grafton Art (graftonart.com), featuring his soul-soothing paintings of rivers, coasts, and dunes, as well as works by his students.

Nestled in a Victorian home, South Street Art Gallery (southstreetartgallery.com) displays a gorgeous collection of local landscapes that will make you pine for more time in natural settings. It’s open Saturdays or by appointment. And don’t miss the lovely Trippe-Hilderbrandt Gallery (trippehilderbrandtgallery.com) with its exceptional photography collection. Taking a monthly First Friday Gallery Walk when the shops are open late and serve refreshments is an ideal way to kick off a weekend.

CULINARY DELIGHTS  Easton’s reputation for creativity includes the culinary arts with a locavore emphasis. With its motto of “dirt to the table in one day,” the Bartlett Pear Inn’s restaurant (bartlettpearinn.com) is touted as one of the best around. Try the chef’s tasting menu with wine pairings. The Inn also recently opened a cozy bakery across the street that sells sweet and savory breakfasts and the best baguettes in miles.

Open for lunch only, the bright Sunflowers & Greens (sunflowersandgreens.com) lets you compose your own salad from such treats as roasted corn and blackened ahi tuna. Drink your fill of antioxidants at nearby Bumble Bee Juices (bbjuices.com) and assume a calming pose between meals at Blue Mat Yoga Studio (bluematyogastudio.com). Thirsty? Hit happy hour at the newly renovated Hunters’ Tavern in The Tidewater Inn (tidewaterinn.com) for two-for-one drinks and half-priced appetizers.

On the way in or out of town, swing by Rising Up (riseupcoffee.com),  a local coffee roaster known for its smooth grounds and scrumptious baked goods. The Peacock Restaurant and Lounge in the Inn at 202 Dover (innat202dover.com) specializes in classic cocktails and fine dining in a Colonial Revival mansion. For al fresco dining and a range of American gustatory options, head to Mason’s (410-822-3204).

ECLECTIC SHOPPING  When it comes to shopping, Easton has something for everyone. For furniture, antiques, lighting, and accessories, don’t miss Bountiful Interiors (bountifuldecor.com), where the name rings true through an eclectic variety of design styles on display, from the classic hunt-country look to a bright and beachy vibe. For unique light fixtures that will add an exclamation point to any room or accessories with that colorful (especially blue) touch that can tie a whole room together, visit the fabulous Dwelling & Design (dwellinganddesign.com). Both shops proffer design services, along with tile, floor and fabric samples.

Bargain seekers will thrive at Tharpe House Antiques & Decorative Arts (410-820-7525), a consignment store run by the Talbot County Historical Society featuring new and antique furniture, crystal, china and books. The eclectic Lanham Hall Design (lanhamhalldesign.com) will have you salivating over select pieces. At Trumpeter Swan (trumpeterswanantiques.com), you may unearth some classic accent pieces and that vintage decoy you can’t live without.

NOTABLE LODGINGS  The Tidewater Inn, a Federal gem at the center of town, recently upgraded many of its rooms to “premier” status. It also offers a spiffy bar and meeting rooms of all sizes. The magnificent Inn at 202 Dover (innat202dover.com) treats guests to internationally themed rooms and a full breakfast, Victorian gardens and high tea on Thursday afternoons. The highly reviewed Bartlett Pear Inn features bright, minimalist rooms and includes a full breakfast at its bakery across the street.

Amy Brecount White explores and writes about the world from her base in Arlington, Virginia.

 

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