Easton is more than Talbot County’s capital. It’s the sophisticated center of Maryland’s Eastern Shore. Home to museums, music venues, galleries and artists’ studios, its vibrant cultural scene draws an international crowd. Add to the mix indie boutiques, critically acclaimed restaurants, significant historic architecture, along with a roster of world-class festivals, and it’s no wonder Easton rates among America’s Top Ten Towns. A host of accommodations, including an historic hotel and a Michelin-noted inn, make lingering easy.


Oxford with its historic homes, picket fences, tree-lined streets, and brick sidewalks is postcard perfect. A pristine small beach, waterfront restaurants, a bookstore, a general store and artisanal ice cream shop round out the offerings. Yachts, powerboats, simple skiffs and the oldest operating ferry in America ply the water—The Tred Avon to one side, Town Creek on the other — casting an air of serenity. It’s no mystery why James Michener chose this as his home base while penning his classic novel Chesapeake. Historic inns and waterfront cottages showcase the best of what Oxford has to offer.

St. Michaels

St. Michaels is a charming waterfront town that beckons visitors to boat, bike or stroll. Shops and cafes flank the main street, plus a trio of tasting rooms invites visitors to try locally crafted beer, wine and spirits. Restaurants run the gamut from crab shacks to fine dining, all with an emphasis on local bounty. St. Michaels’ jewel is the world’s leading museum dedicated to the Chesapeake Bay, and the only place where visitors can explore a rare screwpile lighthouse. Plenty of historic inns and a world-class resort with a golf course invite visitors to stay a while.

Tilghman Island

Tilghman Island is the quintessential Chesapeake Bay village, a place where tradition runs deep. Cross the drawbridge over the Knapps Narrows (the only access to the 2.7-mile island) and you are transported to a slower pace of life. For generations watermen have worked the waterways in pursuit of crabs, oysters and rockfish. Today, Tilghman Island is prime place to take a sailing charter, cruise aboard a traditional boat designed to dredge oysters known as a skipjack or sample fresh local seafood. Stay awhile at one of the quaint family run bed and breakfasts or a stylish rustic chic hotel complete with saltwater pool.

Other Waterfront Villages

Each of the quaint waterfront villages that pepper Talbot County has its own unique character. Bellevue is a sleepy community where you can pick up the Oxford-Bellevue Ferry to cross the Tred Avon River to Oxford. Trappe, a small town surrounding by fields and forests, has a launching ramp right on the banks of the Choptank River. In Tunis Mills, just across an historic bridge with rare wooden decking that crosses tranquil Leeds Creek, you’ll find one of locals’ favorite launching docks, especially for canoes and kayaks. Cordova nestled amid farmland, offers a public boat ramp with courtesy docks. Claiborne’s laidback vibe extends to its small beach where kite boarders chasing the wind and beachcombers searching for sea glass converge. A gentle river runs through Wye Mills, which today is best known for its water-powered mill that’s been in operation since 1682. Bozman, which is set on gentle Harris Creek, is an ideal place for launching kayaks and canoes. Wittman, home to many watermen for generations, has a boat ramp leading directly into the Chesapeake Bay. Neavitt, which is perched beside the Choptank River, is a magnet for crabbers. And the tiny hamlet of Sherwood is home to a full service marina, complete with a lodge and a restaurant where you can plunge your toes into the sand and savor fried oysters while soaking in a killer sunset over the Chesapeake Bay.

Boaters—and those who love the life on the water — have ranked this among their favorites for generations.  The pristine waterfront offers spectacular views of beach, marsh, fields, and forests, along with historic mansions.

Talbot County is always upping its game. Those traversing the Chesapeake Bay will be thrilled to know that the Army Corp of Engineers recently dredged Knapps Narrows, the channel that separates Tilghman Island from the mainland and provides a welcome shortcut to Oxford.  Plus, Talbot County offers two (free) waterfront trail maps that will make your exploration of the area’s waterways a dream. You can find them at

It’s no surprise that many high quality waterfront events take place here, including the 2018 Star World Championship sailing regatta that will draw the best sailors from around the world. These races will be hosted by the Tred Avon Yacht Club in Oxford from October 5-15, 2018.

Whether you have a yacht or a powerboat, you’ll find a comfortable home here. The area boasts many full-service marinas and high quality maintenance facilities, historic towns, and waterfront attractions.

Don’t have your own boat?  No problem. The nautical lifestyle isn’t reserved for those captaining their own boats.  Talbot County is home to many outfitters who can provide kayaks, canoes, and paddleboards for the day so visitors can explore the waterfront.  Plentiful gentle tributaries and rivers mean you need not power through to experience the best of what the area offers. Paddling allows you to slow down and soak in the natural wonders.  

For visitors looking for a waterfront experience without breaking a sweat, no worries.  We’ve got you covered. Sailboats, yachts and working fishing boats can guide you along Talbot County’s waterways.  Or you can hop aboard The Oxford-Bellevue Ferry, the country’s oldest continuously operating ferry, which this year happens to be celebrating its 335th anniversary.  For just a few dollars you can board the ferry—on foot or with your car— and cross the Tred Avon River from the scenic small town of Oxford to the charming hamlet of Bellevue as you take in wide water views, along with glimpses of heron, osprey and bald eagles.

To learn more about the water, the people who work it and the boats that that ply it, head to The Chesapeake Bay Maritime Museum in St. Michaels, one of the finest of its kind in the world.  While there, you can explore a distinctive screwpile lighthouse to get a sense of the spartan and difficult life lighthouse keepers led. And for a hands-on experience, you can even participate in a restoration of a vintage vessel in an “Apprentice For A Day” program.

And no matter what you do, don’t miss a chance to dine at one of Talbot County’s fabulous restaurants, where you can enjoy the fresh crab, oysters, rockfish, skate, and other seafood plucked straight from the water surrounding you.