The Maryland State House and St. Anne’s Church are in view  from the picturesque City Dock along Main Street.
The Visitors Center is a great place to start an Annapolis tour.
Sailors compete in the Wednesday Night Races in waters surrounding Annapolis from April to August.
A draw all year round, Main Street is notable for its quaint shops and varied eateries.
Sights to behold include the Alex Haley Memorial, which commemorates Kunta Kinte’s landing in Annapolis Harbor.
Annapolis boasts historic treasures such as the Maryland Inn.
U.S. Navy midshipmen are a common sight on the city's streets.
Annapolis celebrates Fall Festival in September.
Boat shows take place in the marinas every spring and fall.
Nautical North on Dock Street features custom charts and 3-D maps.
 In the Design District, a mural embellishes In Home Stone.
Artist Nancy Hammond in her studio.
The Ram’s Head Tavern.
The Loews Annapolis Hotel.
Crew teams row by City Dock.
Vin 909 in Eastport features a farm-to-table menu. © Ana Fallon
Steamed little-neck clams, on offer at Vin 909. © Ana Fallon

Harbor City

Annapolis bustles with walking tours, eclectic shops, charming eateries—and a strong sense of history

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 strollable 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 where in 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 travelled 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 a 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 an 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.