Visit our quaint riverside small towns for a unique opportunity to enjoy local charm, uncluttered water views and a sense of calm away from the hustle and bustle of city life. A short drive gets you the chance to exhale and inhale the smells of local fresh catches and the salty air of the Chesapeake’s tributaries.
Once a bustling Royal Port of Entry for the colonies, Chestertown is now a National Historic Landmark District, home to a remarkable collection of Colonial and Victorian architecture and the tenth oldest liberal arts college in the country — Washington College. Downtown is a Maryland Arts & Entertainment District with galleries, studios and creative venues in every block.
For a walkable weekend, book a room in town at the meticulously restored colonial inn, the White Swan Tavern, wherearchaeological exhibits showcase objects found onsite. Unwind on a Friday afternoon with drinks on the deck at the new riverside restaurant and bar, 99 Cannon Riverfront Grille. The restaurant features fabulous river views on three sides and is surrounded by Chestertown’s totally rebuilt municipal marina, so you can watch the boaters tie up. Want an even better view of the river? Reserve your spots aboard the Chester River Packet, a 1920s style tour boat, for a sunset cocktail cruise. For fine dining or a cozy bar supper, reserve at The Kitchen at the Imperial. If you arrive on a Thursday evening, you may be welcomed by the convivial residents who meet in the bar for their weekly Martini Night. Check the schedule at the Garfield Center for the Arts next door, home to some of the finest community theater anywhere.
On Saturday morning, the award-winning Chestertown Farmer’s Market in Fountain Park is the place to be. It’s where the locals start the weekend, catching up with each other’s news in between purchases of fresh local produce, baked goods, plants, meat and eggs.
Locals are also likely to meet over coffee and bagels at Play it Again Sam or return later for a hearty sandwich or salad. The line sometimes snakes out the door at Evergrain Bread Company, where patience is rewarded with a delicious latte and something delectable from the bakery case. You don’t have to be gluten-sensitive to appreciate the array of tasty gluten-free baked goods, quiches, and breakfast sandwiches at Figg’s Ordinary.
Later in the day, foodies will want to stop at Chester River Wine and Cheese Co., a well-curated gourmet mecca for anyone who loves wine, cheese, charcuterie and comestibles. (Owners Jenn and John also run a gem of a kitchen shop a few doors down at Welcome Home.) Tipplers should check out Bad Alfred’s Distilling, where they can sample a selection of locally distilled brandy, vodka, gin and whiskey. Bad Al also serves up pints of lager, stout and pilsner from the nearby Bull and Goat Brewery and makes crisp, satisfying brick-oven pizzas. Scheduled to open in June on Cannon Street is Casa Carmen Wine House and Tapas Bar, serving red, white and rose from Chestertown’s newest winery.
Fashionistas will find plenty of shopping, from chic vintage finds at She-She on High and Walnut & Wool (where owner Sam Arrow’s pet pigs are often in residence) to sophisticated new fashions at Mimi’s Closet. The Dockside Emporium offers stylish casual wear, and newcomer Blackbird Boutique sells well-priced on-trend pieces. Children’s boutique Tiny Tots outfits the fashionistas in training. For gifts and housewares, Twigs and Teacups has long reigned as a browser’s delight, the store that truly has “something for everyone.” Gabriel’s is a popular place to pick up a hostess gift or an affordable accessory. Head up Cannon Street to find two surprises: David Hoatson’s vintage electric lighting and appliance shop, Chestertown Electric, and his son Michael’s high-performance audio store right next door. The Listening Room sells vinyl along with stereo systems to please the most highly tuned ear.
Explore the wealth of galleries starting with Massoni Gallery, a second-floor space at the corner of Queen and High Streets where curator Carla Massonioffers beautiful contemporary artwork by regional and national talents. Massoni also teamed up with five local artisans to open Create, a store thatoffers exquisite handmade furnishings, accessories and jewelry from across the country. Nearby, furniture maker Robert Ortiz welcomes visitors to the spacious studio where he shapes wood slabs into beautifully crafted tables, cabinets and other functional pieces. Another group of artists runs Artists’ Gallery, with an ever-changing display of paintings and crafts. Completing the visual arts tour, Brady Hart Gallery sells a mix of fine art by accomplished artists both living and dead, with a specialty in American Impressionists. And the nonprofit RiverArts gallery stages a new members show monthly. Right across the breezeway you may catch the couple behind Hegland Glass piecing together and firing their striking glass bowls and platters.Book lovers must stop by The Bookplate, a browser’s paradise and the center of local literary life beyond Washington College.
Delve into local history at the centrally located Bordley History Center, home to the Historical Society of Kent County, where you can pick up a brochure with a comprehensive historic and architectural walking tour of downtown (also available at the Visitors Center, Maple and Cross). Sumner Hall, a former G.A.R. Hall founded by African American veterans of the Civil War, is a couple of short blocks off the main shopping streets. Open Saturdays and by appointment, its first floor holds interesting displays on local African American history.
Start your day in Denton at the Wharves of Choptank Visitor Center on the Choptank River. While you’re there, check out the “Snapshot in Time” murals beneath the the bridge that show what life was like on the bustling steamboat wharf.
Next, make your way into Downtown Denton – just a short walk up from the river. You’ll find delectable pastries and treats made by Food Network finalist Chef Steve Konopelski at the Turnbridge Point Shop. Chef Steve also offers baking classes, so roll up your sleeves and learn something new!
A short walk to the Denton Artsway will bring you to the Foundry Community Arts Galleryand the Fiber Arts Center of the Eastern Shore (FACES). Home of the Caroline County Council of Arts, the Foundry features works in all media by local artists. At FACES, you’ll find rotating exhibits of historic and contemporary works by fiber artists from throughout the Delmarva Peninsula.
For lunch, head to the Market Street Public House – a local favorite that serves up a delectable fusion of Irish-American fare. The Pub is located right on the Courthouse Green in the heart of Denton. Be sure to check out the surrounding shops, including Joviality, which features gifts, home decor and more!
History buffs will want to be sure to visit the Museum of Rural Life, which offers visitors a rare glimpse into Caroline County’s agrarian history. The exhibits feature portions of four historic houses, including an entire circa 1824 log cabin.
Next, make your way to Shore Gourmet Denton Market, located within the Chesapeake Culinary Center. Here you’ll find specialty food items grown and produced in the Chesapeake region. From cheese to chocolate, you’ll find a variety of delicious treats to take home.
Those looking for an outdoor adventure can rent a kayak or Boston Whaler from Mathews Landing Rentals and explore the upper reaches of the winding Choptank River,
End your perfect day with handcrafted cocktails and fine dining at Harry’s Food & Spirits. Enjoy the views from the wrap-around porch, or sit by the crackling fire and recount the day’s adventures. You belong here.
Kick off your day at the Ward Museum of Wildfowl Art located at 909 S. Schumaker Dr. Discover the artistic vision of wildfowl sculptors who strive to capture the spirit of the natural world. While touring the galleries notice the exquisite details of lifelike sculptures that appear ready to take flight. Be sure to stop by their gift shop Treetops. They carry a wide range of hand- made jewelry, decoys and nature themed home and outdoor décor.
After visiting the Ward Museum, grab lunch along the Wicomico River at Brew River, voted Maryland’s Best Bar and Seafood Restaurant, there is something for everyone. After lunch, head across the street and grab a slice of pie from our friends at the Ugly Pie and shop for unique handcrafted art at Chesapeake East at 501 W. Main St.
Then make your way up the Plaza and visit some of the locally owned shops in Downtown Salisbury. Not to be missed, head to Salisbury Art Space and the SU Downtown Art Gallery to check out an art exhibition.
Looking for a casual cocktail? Stop in to Roadie Joe’s Bar and Grille across the street from the galleries. From burgers to cheesesteaks to melt in your mouth scallops, their food is simply delicious!
Snow Hill, MD
Come enjoy a Friday in Snow Hill! Start off your day with a coffee and lunch at Daily Brew Coffeehouse! Rent a kayak from Pocomoke River Canoe Company and grab some photos on the river. Round out your morning with a visit to Nancy Thompson Art Studio where she can teach you how to paint that photo on canvas or she can do it for you!