Boaters enjoy easy access to the marinas at the Inn at Haven Harbour.
No visit is complete without an ice cream float at Durding's Store, housed in a building from 1872.
Beachcombing in the Eastern Neck National Wildlife Refuge.
A Rock Hall sojourn may include a stroll on the dock at Osprey Point.
The Inn at Hungtingfield Creek boasts a sea of sunflowers on its property.
Items for an al fresco meal, courtesy of Vintage Picnic.
Unique items are available at the Hickory Stick.
Young mariners embark on a Rock Hall Yacht Club Sailing School course.
The Waterman's Museum chronicles the town's fishing, oyster and crabbing industries.
Durding's Store awaits on Main Street.
Pirates & Wenches Fantasy Weekend attracts cosseted revelers from August 10 to 12.

Up-and-Coming Rock Hall

First settled in 1706, this once-bustling fishing village now comes alive for recreational boaters and visitors—at least in season

Geography 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.