Visit Where The Locals Play

County of Kent on Maryland’s Upper Eastern Shore


Many describe the shores of the Chesapeake Bay and its tributaries as breathtaking and relaxing, for there is something that touches the human senses when water abounds. Maryland’s smallest county, the County of Kent, is a perfect example of how a getaway destination is able to release stress from our body and minds. The peaceful vistas and beautiful landscape of rolling hills, farms, vineyards and open space reminds us of a time past, when life was simpler. Enjoy the peace and beauty, but be ready to have fun, for this quaint countryside is host to hundreds of events. Combine an event with the many attractions, recreational activities, local fresh foods, natural history, shopping, musical and theatrical performances, and you have the beginning of a perfect escape.

Historic Towns

Its historic towns and villages, such as Chestertown, Rock Hall, Galena, Millington, Betterton, Fairlee, Kennedyville and Georgetown, are packed with history, some with more than 300 years of perseverance, turmoil, triumph, hard work and prosperity. Those who reside in the County of Kent know what it’s like to live where visitors come for fun and relaxation. Pride of sharing their heritage, waterfront, landscape, music, wine, and enjoyment through festivals, events, tours and more is the cornerstone of this special place.

Driven by its location along the Chesapeake Bay, there are many ways to “get on the water” in the County of Kent; in fact, you will find dozens of marinas throughout the County. Charter a boat with a licensed captain, who is ready to take you for a sail, cruise or fishing. Calm rivers and creeks set the perfect conditions for paddling. Look for a licensed guide, join one of Sultana’s themed guided tours, or paddle yourself along the three most beautiful water trails you will ever experience: Chester River Water Trail, Sassafras River Water Trail and Eastern Neck Island Water Trail.

Outdoor Recreation

Bring your bicycle or rent one to get out on flat, winding country roads. You may even find yourself on the Chesapeake Country National Scenic Byway. Or take a ride to Eastern Neck National Wildlife Refuge, only seven miles from Rock Hall, where you’ll find walking trails, picnic areas, fishing spots, observation decks, launch ramps and more.


Undoubtedly, this outdoor exercise will work up an appetite, but not to worry, there are plenty of ways to eliminate those hunger pains in the County of Kent. Known for its terrific restaurants, you will find one here for every taste. From mouth-watering burgers to gourmet seafood and beef entrees, the flavor is yours to choose. From waterfront vistas to historic red-brick sidewalks, the view is yours to pick. And, summer is the season for picking — picking crabs that is — find the Chesapeake Bay Blue Crab at a waterfront restaurant in Rock Hall or pick up a bushel from a local seafood company. Now if you want to catch your own dinner, try your luck at fishing. You may choose from more than two-dozen licensed fishing captains to get you to their favorite fishing holes on the Chesapeake Bay. Find the list of the charter captains at


Be sure to leave enough time for shopping. From the whimsical shops and antique stores of Rock Hall and Galena to boutique shops and art galleries in Chestertown, you will find one-of-a-kind gifts and enjoy old fashion, friendly service. Teeming with “Made in Kent County” vendors, don’t miss the award winning Chestertown Farmers’ and Artisans’ market, which begins every Saturday morning at 8 a.m in Downtown’s Fountain Park or the outdoor markets in Rock Hall and Millington too.


Music lovers will not want to miss a show at the Garfield Center for the Arts in Chestertown or the Mainstay in Rock Hall. Before the show, try a wine or spirits tasting at Crow Vineyard and Winery in Kennedyville or Cassinelli Winery and Distillery in Downtown Chestertown. You will also want to try a craft beer tasting at Chester River Brewing Co. in Chestertown. Whether cycling, bird watching, getting out on the water, taking a nature walk on one of Eastern Neck National Wildlife Refuge’s trails, exploring history, touring or having fun at one of the many events, you will fall in love with this very special Chesapeake Bay region called the County of Kent. For more details, visit


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