The Most Charming River Towns In Maryland
Maryland's rivers wind east toward the Chesapeake Bay, and Chestertown still lines the banks of the Chester River with the 18th-century Colonial architecture of an old port town. Havre de Grace guards the mouth of the Susquehanna behind its restored 1827 lighthouse, and Snow Hill sits on the tea-colored Pocomoke, dark with cypress tannins. Together, these seven towns trace the water routes that once carried Maryland's trade down to the bay.
Chestertown
Chestertown is renowned for its stunning 18th-century Colonial architecture, maritime heritage thanks to the Chester River, and local culinary scene. On the banks of the Chester River is Wilmer Park, a quaint and relaxing green space with a wonderful picnic area, a gazebo, and the 0.3-mile-long Wilmer Park Loop for a calming walk with the river in view. The park hosts annual community events like the Chestertown Jazz Festival, which features local and regional artists performing soothing jazz, gospel, and blues, creating a family-friendly atmosphere with the river glimmering in the background.
Up Cannon Street is Modern Stone Age Kitchen, a restaurant serving food made from scratch using traditional methods like sourdough fermentation. Customers can order sourdough pizza, baked chicken wings, fermented French fries, and MSAK breakfast platters to start the day or enjoy a satisfying brunch or lunch. The Chestertown Marina, which sits on the Chester River, allows people to rent and store boats to explore the open waters, and provides fuel sales, winter storage, and kayak and canoe launching stations. The Marina is a wonderful place for boat enthusiasts to gather, as they go on fishing expeditions or have a delightful day on the water.
Havre De Grace
Havre De Grace sits where the Susquehanna River meets the Chesapeake Bay. Residents and visitors get stunning views of the surrounding landscape and bay, plus the historic landmarks that line its shore. The Concord Point Lighthouse, restored and dating to 1827, is preserved by the Friends at Concord Point Lighthouse, who keep its history alive for today's visitors. Millard Tydings Memorial Park is a wonderful waterfront spot with views of the bay and Park Island. From there, people can walk down to the Havre De Grace Basin Marina for access to water. The park also has a playground, pickleball courts, and a small gazebo for community events.
Near the park is the Havre De Grace Decoy Museum, showcasing one of the finest collections of decoys, their place in Chesapeake culture, and how they are carved for hunting. The museum also displays historic hunting boats, sink boxes, folk art, and carved decoys. The Market Street Brewery is an exciting place to grab a drink in town, as it has a diverse beer selection to choose from, like Eastbound & Brown, the Easy A, and the Stillwater, to name a few. The Brewery also offers stunning views of the Susquehanna River and is a great place to host small get-togethers and private events.
Brunswick
In southern Frederick County, on the state line, is Brunswick, a historic railroad and canal town thanks to the Potomac River and the Chesapeake and Ohio Canal, and a hub for outdoor activities. The Brunswick Family Campground sits on the Potomac River, giving locals and visitors a place to camp for the night, fish, and hike the Brunswick Family Campground to Landers Boat Dock trail, while an adjacent boat ramp opens up boating, canoeing, and kayaking. The site offers basic cabins, a place to park motorhomes and trailers, and is pet-friendly. Another trail to explore is a local stretch of the Chesapeake and Ohio Canal Towpath, where hikers, walkers, and bikers can take in the calm views of the canal and the adjacent Potomac River, and the sounds of nature.
A friendly place in town to grab lunch is Boxcar Burgers, serving classics like the Boxcar Burger, cheese fries, the pickler, and rodeo fries. Boxcar Burgers started as a food truck serving burgers at craft breweries and private events before expanding to more permanent restaurants in Brunswick and Middletown, while continuing to serve delicious, locally prepared meals. Just west of Boxcar Burgers is the Brunswick Heritage Museum, where visitors can learn more about the city's history, view HO-scaled model railroads, and browse exhibits of photographs, artifacts, and other items preserved from the past. The museum also hosts community events and educational programs that bring residents together around the town's history.
Cambridge
Cambridge, near the mouth of the Choptank River, has a rich maritime heritage and deep ties to the Underground Railroad. Seafood from the Chesapeake Bay is abundant. The Richardson Maritime Museum is a place to explore and learn about the city's history and maritime culture. The museum sits on four acres of waterfront property, with two main buildings and a growing outdoor collection of maritime artifacts. It also hosts events, lectures, and boat cruises. On Cambridge Creek, Portside Seafood Restaurant serves boom boom shrimp, cream of crab soup, crab cakes, and steamed mussels. There's outdoor seating overlooking the creek and the boaters cruising by, and the restaurant can host private parties and events.
On the other side of Cambridge Creek is the Harriet Tubman Museum, which honors Tubman, who was born in Dorchester County. The museum shares her story, her perseverance, and the origins of the Underground Railroad. Visitors to the museum can also take walking tours of the Underground Railroad in downtown and outside of town, accompanied by banjo music afterward. Near the mouth of the Cambridge Creek is the Cambridge House Bed & Breakfast, where guests are treated to a relaxing atmosphere, waterfront views of the adjacent river, and rooms that transport them back to the 19th and early 20th centuries, all equipped with modern amenities. The bed and breakfast also features a lily pond and garden, a tranquil setting for guests to enjoy their morning coffee and breakfast in blissful style.
Solomons Island
Near the mouth of the Patuxent River is Solomons Island, a coastal village on the Chesapeake Bay with a rich maritime history and an incredible seafood scene. The iconic Solomons Island Boardwalk is a pleasant place to enjoy scenic river views and a vibrant atmosphere, with local shops, galleries, and restaurants across the water. One of those restaurants is the Island Hideaway, a seafood spot with stunning waterfront views and a welcoming interior. It has outdoor seating, and boats are docked at the residential homes. The Island Hideaway serves a delicious selection of seafood, wines, beers, and cocktails, and maintains a lively, upbeat atmosphere.
A relaxing place to spend the night or weekend in town is Solomons Victorian Inn, a quaint and alluring bed and breakfast with elegant rooms, a delightful breakfast to begin the day, and glorious shared sitting rooms. The Inn is a splendid place to gather for small weddings or elopements in style with the stunning bay as a perfect backdrop. A wonderful bar for gathering with friends and family during the summer is Tiki Bar Solomons, where patrons can order delicious seafood dishes such as crab cake burgers, fish tacos, and island salmon. The bar serves refreshing specialty drinks like a mai tai, blue tiki, and a Maryland mule, keeping the night young and interesting.
Snow Hill
On the banks of the Pocomoke River, on Maryland's lower Eastern Shore, is Snow Hill, a historic 17th-century port town known for its scenic waterway, well-preserved architecture, and outdoor recreation. The Pocomoke River, designated a scenic river by the state and tinted a deep tea color by cypress tannins, is the town's main draw for paddlers, and the Pocomoke River Canoe Company rents kayaks and canoes for trips through the surrounding cypress swamps and wooded creeks. Right in town is Byrd Park, a leafy 15-acre green space along the river with a playground, basketball courts, picnic areas, and a public boat launch for easy access to the water.
In the heart of downtown is the Julia A. Purnell Museum, housed in the 1891 former St. Agnes Catholic Church, where visitors can explore Worcester County history through exhibits on the Victorian era, local trades, and the needlework and textile art of the museum's namesake. A few miles outside of town is Furnace Town Historic Site, a restored 19th-century village built around the Nassawango Iron Furnace, where blacksmiths, broom makers, and other artisans demonstrate traditional crafts and guests can tour the grounds and museum. Back downtown, Bishop's Stock combines a fine art gallery with a wine shop, showcasing rotating exhibitions of painters, sculptors, and ceramic artists from the region for a relaxing afternoon stop.
Hancock
On the Potomac River at the western end of the state is Hancock, a premier "trail town" known for its 28 miles of paved trails, breathtaking views of the Appalachian Mountains, and agricultural roots. The 1878 RiverRun Bed and Breakfast is a great place to spend the night or a weekend in town, offering views of the Chesapeake and Ohio Canal and the Potomac River, cozy rooms, and a peaceful, historic atmosphere. The Western Maryland Rail Trail is an ideal natural wonder to explore, as it's about 28 miles long, surrounded by towering trees, and a perfect place to go hiking, biking, and running. The trail is near the Indigo Tunnel, which is home to eight different species of bats, and by the end of the trail, people can visit museums, restaurants, and shops in town.
On High Street is the Hancock Town Museum, which preserves the town's history, with a particular focus on transportation and local life. The museum has a nicely preserved collection of antique tools, memorabilia, and artifacts related to the Chesapeake and Ohio Canal. On the eastern end of town is BuddyLou's Eats, Drinks and Antiques, a local restaurant housed in a cottage serving craft beer, sandwiches, soup, and a full bar for patrons to enjoy. The restaurant also has an antique store selling glassware, pottery, historic bottles, vintage toys, and record players, making for one of the more interesting places to visit in the state.
All Rivers Flow to the Chesapeake Bay
Every one of these towns stays close to the water. Snow Hill sits on the banks of the Pocomoke River; Cambridge carries a deep-rooted maritime history along the state's eastern shoreline; and Havre de Grace keeps its museums at the mouth of the Susquehanna, where the river meets the bay. Rent a canoe from the Pocomoke River Canoe Company in Snow Hill, and you are paddling the same tea-colored water that once carried Maryland's trade down to the Chesapeake.
