A Different Kind of Shore

by Tracey Meloni

Rock Hall. Courtesy of Kent County
Rock Hall. Courtesy of Kent County

A funny thing happened on the way to the shore: the discovery of picturesque and historic sites and towns around the Chesapeake Bay. Not a single town but a whole rural region to explore, the bay area has enticed previous generations: George Washington, Tallulah Bankhead, Eric Clapton, Thomas Jefferson and Charlie Byrd have discovered hidden gems like Rock Hall and Chestertown and made them their exploration, if not their destination.

Head north to Maryland’s Sandy Point State Park, a 786-acre mini beach treasure located just this side of the Chesapeake Bay Bridge. Since 1952, Sandy Point has inspired family memories. Open year-round, Sandy Point is a site on the Chesapeake Bay Gateways Network. The park’s beaches and picnic areas are well-known for scenic water views overlooking one of our true treasures, the Chesapeake Bay.

From the park, head east over the Bay Bridge to historic Kent Island. As you face Kent Island with the bridge behind you, Love Point is to your left, Metapeake Beach to the right (one of the top dog-friendly beaches in Maryland). Also overlooking the bay and bridge is Terrapin Nature Park, another Fido-friendly spot. (Tip: check online for parking information or other requirements.)

ROCK HALL, Maryland

All roads lead to water in Rock Hall. Located directly on the National Chesapeake Scenic Byway, Rock Hall is a jumping-off point for venturing back into history and preservation and forward via biking, hiking, fishing and boating. And swimming—Rock Hall has its own bayside beach.

    Don’t miss the Rock Hall Museum and Waterman’s Museum for vivid depictions of history and the challenging waterman’s life; discover decoy carving, fabulous skipjacks and other working boats.

When it’s time to refuel, try Waterman’s Crab House, with breathtaking views of the Bay and award-winning casual dining: crabs, barbecued ribs, steamed jumbo shrimp. Rock Hall has free concerts, boat races, food fests and Waterman’s Days. 


Named for the Chester River that it faces, Chestertown offers up history, arts, shopping and varied lodging and dining experiences. Home to the Schooner Sultana, Chestertown provides a link to the maritime heritage of the Chester River and the Chesapeake Bay. The town is also home to Washington College, a private liberal arts school dating back to 1782.

The county seat of Kent County on Maryland’s upper Eastern Shore, Chestertown centers a rich tapestry of farmland and Chesapeake Bay estuaries that almost surround the county with water. 


Terrapin Nature Park. Courtesy of Queen Anne's County
Terrapin Nature Park. Courtesy of Queen Anne’s County

Sandy Point State Park: Swimming beaches, picnicking, fishing, crabbing, boating, hiking and (for longer trips) camping are offered. The park also has a marina store and boat rentals. Wildlife viewing and bird-watching are favorite pastimes thanks to Sandy Point’s location on the Eastern Flyway. // dnr.state.md.us

Cross Island Trail: A repurposed rail trail and part of the American Discovery Trail, it spans Kent Island from Terrapin Nature Park to Kent Narrows, a distance of about 6 miles. There are several places along the way where you can park and enter the trail, including Old Love Point Park, Castle Marina Road, Kent Narrows Boat Launching Ramp and the Chesapeake Bay Exploration Center. // findyourchesapeake.com

The National Chesapeake Scenic Byway: This byway meanders from Rock Hall to Chestertown, Maryland, a treasure hidden in plain sight according to the National Trust for Historic Preservation, which calls waterfront Chestertown “an ideal retreat.” // chesapeakebyway.org

The Chesapeake Wine Trail: Follow the Chesapeake Wine Trail and discover yet another reason to love the region, with delicious and appropriate accompaniments. // chesapeakebaywinetrail.com

Love Point: The northernmost tip of Kent Island, legendary for separated lovers, Love Point is a destination for engagements or vow renewals—or maybe just romantic picnics.


Courtesy of Delmarva Ballon Rides
Courtesy of Delmarva Ballon Rides

Delmarva Balloon Rides: You, champagne, a ring and new promises as a colorful balloon soars silently over the Chesapeake, or maybe you and the one you’ve loved for 25 years making new vows. Delmarva Balloon Rides make all occasions special. Call for personalized planning with veteran pilot Todd Davis. Whether your goal is high-soaring or tethered partying, fun is in the air.

Mutt Strut: The Fifth Annual Mutt Strut Extravaganza on  April 22-24 at Wilmer Park in  Chestertown is “the biggest doggie celebration in years,” say planners. This year’s weekendlong extravaganza showcases activities including  food trucks, children’s activities, live music, a family-friendly 5K run/walk and “our long-standing tradition of parading our four-legged friends through town.” 

Taste of the Town: May 1, noon-3 p.m. One of Chestertown’s signature events, it pairs restaurants and diners, farms and chefs from throughout the county. Sample dishes include everything from crab soup to pulled pork, fresh mozzarella appetizers, gnocchi and Mexican hot chocolate brownies. Local beers and wines are also on hand. In the demo booth, chefs will create dishes from a mystery basket of local foods. Tickets available online in advance and at the door.

PORCHFEST: May 14, noon-5 p.m. A progressive, open-air music festival pairing local talent with historic homes and downtown shops. “Lineup and map will be presented as plans are cemented,” the organizers say. See Chestertown website for more information.

Chestertown Tea Party: May 27-29 An annual, very American reenactment, Chestertown joins Boston in celebrating history. “The festivities start on Friday evening with a family-friendly street party: good food, games, entertainment and music. “On Saturday we commemorate the local citizens’ revolt against the British Tea Tax,” says organizing spokeswoman Sabine Harvey. “The day starts with a 5K and 10-mile run, followed by a colonial parade, colonial demonstrators and the actual reenactment, starting at 2 p.m. In addition, enjoy great food, music, entertainment and craft vendors. Sunday features a wine and beer tasting event, craft vendors and a raft race of homemade rafts trying to stay afloat as long as they can.


Courtesy of Chester River Wine and Cheese Co
Courtesy of Chester River Wine and Cheese Co

Quaint shops featuring personalized service and specialized ingredients characterize area offerings. Don’t miss these unique treats.

• Chester River Wine and Cheese: Owners John Laucik & Jennifer Baker “offer domestic and international small-batch gourmet foods with a focus on wine and cheese. Our shop offers both retail and onsite wine by the glass and cheese boards,” Baker says. “It makes living and working here fun, which is exactly why we came.” 

• The Hickory Stick: Bayside in Rock Hall, Maryland, is a unique boutique with a selection of some of well-known lines including Brighton, Vera Bradley and Lindsay-Phillips Switchflops. Visitors say the shop is “within two hours of everywhere.” 

• If you happen to visit the region on a Thursday, check out the Kent Island Farmer’s Market, 3:30-6:30 p.m. year-round to pick up free-range chickens and eggs, homemade dog treats and locally sourced farm items.

• Simpatico St Michaels: All things Italian on the Eastern Shore: ceramics, gift items, pasta, specialized scarves.


inexpensive option Ellen’s Coffee Shop 205 Spring Ave., Chestertown, facebook.com/Ellens-Coffee-Shop-Family-Restaurant Family fare, friendly service. more expensive option Ram’s Head Shore House 800 Main St., Stevensville, ramsheadgroup.com Beaucoup Benedicts, huevos rancheros, “The Montoya,” grits, French toast and all the usual suspects. local favorite Beverly’s 11 Washington Square Shopping Center, Chestertown, facebook.com/BeverlysFamilyRestaurant Homecooking served up fast and friendly, all day long.
inexpensive option Fish Whistle 98 Cannon St., Chestertown, fishandwhistle.com Drunken clams and mussels, mac and cheese, meatloaf, Eastern Shore platter. more expensive option Fisherman’s Inn 3116 Main St., Grasonville, fishermansinn.com Shrimp, crab, oysters and, yes, burgers. local favorite The Narrows Restaurant 3023 Kent Narrow Way S., Grasonville, thenarrowsrestaurant.com Ahi sliders, crab cake twins, black and blue steak sandwiches.
inexpensive option Waterman’s Crab House and Dock Bar 21055 W. Sharp St., Rock Hall, watermanscrabhouse.com Crab, crab and more crab. more expensive option The Kitchen Hotel Imperial: 208 High St., Chestertown, imperialchestertown.com Lovely and palate-pleasing, this long-standing but newly owned landmark promises the best of the Chesapeake. local favorite Fisherman’s Inn 3116 Main St., Grasonville, fishermansinn.com “Nauti-Mermaid” bar, lobster bisque, fried oysters, crab cakes—the best.

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