Plan Your Chestertown Visit With Three Great Itineraries: Recreation, Culinary Arts and History


GET OUTSIDE: Suggestions for outdoorsy types

Throw the kayaks or bikes on the car and escape to Chestertown and the surrounding county—full of gorgeous Chesapeake landscapes, secluded waterways, and hikes.  Chestertown is the perfect launch site for all kinds of outdoors adventures—and a great place to rest, relax and fuel up for your next day on the river or trail.

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Packing a hearty picnic is a must, so be sure to stop by Evergrain Bread Company for a sandwich on a baguette, or Chester River Wine and Cheese for a lunch spread of cold sandwiches or hummus, charcuterie and cheese. For delicious gluten-free options, stop by Figg’s Ordinary to choose baked goods, quiche, salads and sandwiches. Then grab some fresh organic fruit or kombucha at Chestertown Natural Foods and you’ll eat like royalty in some of the loveliest scenery in Chesapeake Country.

The quiet waters of the Chester River provide some great options for kayakers, cyclists or paddleboarders, all within easy proximity of Chestertown, and local parks and wildlife refuges have some stellar hikes.

Our favorite paddle: Put in your small craft at Morgnec Landing as the tide is coming in, just off route 291 by the baby blue truss bridge. Paddle upstream on the lovely, unspoiled Morgan Creek, where you’ll see osprey, heron rookeries, river otters, and bald eagles—and probably not another soul on your whole trip. After about 45 minutes, you arrive at Riley’s Mill public landing—a great picnic spot before you head back the way you came. Once you’ve wrapped up your epic paddle, celebrate your day of calorie-burning adventure with a round of craft brews and an order of pulled pork nachos at Smoke Rattle and Roll.

A walk in the woods: A 20-minute scenic drive from Chestertown is Eastern Neck Island National Wildlife Refuge. Once inhabited, today this 2,285-acre island is covered in pine forests, verdant marshes, and fields—the perfect habitat for all sorts of migratory waterfowl, eagles, osprey, terrapin and other Mid-Atlantic species. Don’t miss the Duck Inn Trail, a 1-mile hike that takes you through forests and marsh to arrive at a gorgeous vista overlooking the Chester River.  Leashed dogs are welcome, so bring your pup along! Once you’ve finished your hike, reward yourself with a hand-dipped ice cream cone at Durdings Store, a former 19th century pharmacy in Rock Hall with its original soda fountain.

Pedal through the past: One of the oldest Kent County roads, Quaker Neck Road, begins in Chestertown and threads through the 18th century farmland adjacent to the river. Follow the fork to your destination in Cliff City, an old Chester River steamboat wharf (and still working boat ramp). A 20-mile round trip, it’s a relaxed, hour-long bicycle ride from Chestertown to Cliff City. You’ll be rewarded by glimpses of colonial homes, pedaling through shady avenues of trees and passing churchyards and a classic red schoolhouse. Take a breather, catch a gorgeous view and graze on some grub at the landing, then turn around and head back to Chestertown. It’s a great, slow way to see some of the most pristine farmland left in the Chesapeake region. Once you’ve cycled your way back to Chestertown, continue your river daydreaming with a cold glass of wine and a very modern burger at the Fish Whistle, built on the site of Chestertown’s 18th century wharf.

Crabcakes are an Eastern Shore specialty and there's lots more. Photo by Carolyn Spencer Brown.

LOCAL FLAVOR: A taste experience for foodies 

For unabashed foodies, Chestertown has a lot to offer. From the award-winning farmer’s market to local shops stocking fine wines, locally distilled liquors, imported cheeses and locally aged beef, culinary adventures await in the historic downtown and surrounding Kent County countryside.

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Saturday Special:  On Saturday morning from 8 a.m. to noon, running from the third Saturday of March through Christmas, the Chestertown Farmer’s Market is the place to find incredibly fresh local produce, baked goods, plants, meat and eggs—as well as a wide selection of crafts made by regional artisans.   This award-winning market is where the locals start the weekend and catch up with each other’s news.

Locals are also likely to share a latte and a breakfast bagel at Play it Again Sam’s. The café on Cross Street is a long-time meeting spot with a casual, laid-back vibe.

High Spirits: Love cocktail hour? Chestertown’s got you covered. Tipplers should check out Bad Alfred’s Distilling on High Street, where a selection of their own locally distilled brandy, vodka, gin and whiskey is sure to put some sparkle in your eye and hair on your chest. Sample the good stuff in their tasting room (you can always buy a bottle or two to take home) and settle in for the afternoon with some of their live music and crisp, satisfying brick oven pizzas. And for folks who prefer something a little lighter in their glass, Bad Alfred’s also serves up pints of lager, stout and pilsner from the nearby Bull and Goat Brewery. 

Wine About It: The Chester River Wine and Cheese Co. is a gourmet mecca for anyone who loves well-curated wine, cheese, charcuterie and comestibles. Prepare to leave with your shopping bags bulging after browsing their selection of bright rosés, rich cheeses, and sharp, spicy sausages. They also carry an extensive array of mustards, sauces, crackers, cookies, chocolates, and other things to serve with your handpicked cheese board. The staff is happy to provide tastings of new cheeses or suggestions for how to up your cocktail party or evening in. Thanks to a change in the shop’s liquor license, you can now sit a spell at its indoor and sidewalk tables and enjoy wines by the glass along with their delicious sandwiches, salads and cheese & charcuterie boards. 

Back to School: A fifteen-minute drive from Chestertown through rolling farmland is the village of Kennedyville, where you can find one of the county’s culinary gems, K&B Market and Kitchen School. Here, chef Kevin McKinney and wife Barbara (the K and the B, natch) make scrumptious carryout meals that are the perfect antidote to the midweek “don’t feel like cooking” quandary. Check their website ( for weekly menus and market hours. For the ambitious foodie, schedule a custom cooking class, where would-be Julia Childs can create a meal of their choice from scratch alongside Chef McKinney and a few of their closest friends. Beer and wine is included—and is chosen to compliment your meal. So throw on an apron and get ready to do your best Gordon Ramsay as you slice, knead, mince, boil, and roast your way through a truly memorable and delicious evening.

Queen Street

PAST IS PRESENT: Exploring a sense of place and history. 

In a town with a rich past and so many extant historic buildings, Chestertown has long been a draw for history lovers of all ages. From its brick cobbled sidewalks to its impressive colonial waterfront mansions, Chestertown’s history is a big part of what makes it unique—and also makes it the perfect getaway for history buffs.

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Over 300 years, Chestertown has seen great changes—and many of its buildings, museums, and civic spaces tell fascinating stories about how national, regional, and local events shaped the community over time.

Walking through time: Chestertown’s Visitor Center, the red brick building at the intersection of N. Cross Street and Maple Avenue, offers a brochure with a comprehensive historic architectural walking tour of downtown Chestertown. Many of the town’s remaining 18th century houses are discussed in detail, from the Buck-Bacchus House (a colonial store) to the Customs House at the waterfront, where imported goods from around the world were brought in by sailing vessels to Chestertown’s Port of Entry. Pick up a tour map to follow along as you walk through shady streets that, except for an automobile or two, haven’t changed much in over 200 years. A convenient place to stop along the way for an elegant bite and some liquid refreshment is The Kitchen, where you can eat in the cozy bar or, in good weather, dine al fresco on the front sidewalk or back courtyard.

A blast from the past: Centrally located in downtown Chestertown, the Bordley History Center is the home of the Historical Society of Kent County. A former storefront, the plate glass windows that once displayed merchandise are now mini-exhibits featuring stories and subjects from the county’s rich history. Call ahead to dig deeper into their comprehensive research library, where genealogical sleuths can peruse ledgers, maps, genealogies, cemetery records, photographs, original architectural drawings and oral histories, and stop in the Center’s gift shop for books of local history or historically-inspired gifts.

Explore Sumner Hall: One of only two existing African American G.A.R. buildings still standing in the United States, G.A.R. Sumner Hall is a civic space created in 1908 by local African American Union veterans from the Civil War, as part of a group known as the Grand Army of the Republic. A hub of African American social and cultural life for six decades in Chestertown, jazz notables performed on Sumner Hall’s stage. After falling into disrepair in the 1950’s, the site was restored by a coalition of preservationists, philanthropists and locals, ultimately reopening in June 2014.  Today Sumner Hall welcomes visitors on Saturdays to explore its exhibits documenting African American life, history, and culture in Kent County.

Tea for Two: After exploring Chestertown’s fascinating history, head over to afternoon tea at the White Swan Tavern, offered from 2 to 5 p.m. Quaff a cup of the good stuff and nibble through some finger foods inside by a warming fire in winter, or take it outside to the back lawn to enjoy a lovely spring day. This beautifully restored 18th century “public house” turned B&B offers cozy overnight lodgings. History lovers will enjoy the lovely period atmosphere and the archaeological exhibits; all objects were found onsite during the restoration of the Tavern in 1978.

Plan your trip to Chestertown with these three trip itineraries!