9 Small Towns In Maryland To Visit For A Weekend Getaway
Maryland is one of the United States' original 13 states and is part of a populous, economically vibrant region on the Eastern Seaboard, stretching from Maine to Virginia. Geographically, it sits adjacent to the Chesapeake Bay and encompasses the Appalachian foothills to its west. Given its rich history and diverse culture, it should come as no surprise that this is a fantastic place for vacation. If you are looking for a fantastic weekend getaway, consider visiting any of these 9 small Maryland towns.
Saint Michaels

Arrivals in Saint Michaels will find themselves along the Miles River, perfect for those who love time on the water. An ideal option for a place to stay is the St. Michaels Harbour Inn, Marianna, and Spa. This waterfront inn puts you at the heart of the area's most popular activities. While walking along the docks, you can head for a tour on the Saint Selina II. Moonlight cruises, wine tastings, and general river tours are all available within walking distance. Also within walking distance is the waterfront shopping area along South Talbot Street. The area is dotted with shops and dining locales to enjoy while you walk near the river. For those who want to learn more about the region's relationship with the water, the Chesapeake Bay Maritime Museum offers an in-depth look at the history of the Chesapeake Bay. Historic vessels dating back over a century are maintained and afloat on the river, while indoor displays feature tales that date back to the War of 1812 and the conflicts that erupted on the bay.
Berlin

Berlin is a town of live music, culture, and art. Visitors to town will want to head to the Holland House Bed and Breakfast for a cozy stay, where they can enjoy uniquely themed rooms and a delicious breakfast in the morning. From here, you will be within walking distance of Historic Downtown Berlin. The nearby Welcome Center on Main Street is the start of an afternoon filled with shops and restaurants. Visitors can enjoy farmers' markets, live jazz and blues, and art festivals. They will also be close to the unique destination, The Mermaid Museum. The museum showcases the history of mermaids in American culture through a collection of artifacts and artwork. As just one example, the historic P.T. Barnum once advertised that it was possible to see mermaids at his circus, and the advertisement is currently on display in the museum. Around the corner, you can find the Worcester County Arts Council, which focuses on promoting art from creators in the county. Themed exhibits feature miniature works and landscapes, as well as oil and mixed-media presentations.
Havre de Grace

Another waterside location perfect for those who want to enjoy the shores is Havre de Grace. Located on the banks of the Susquehanna River and the Chesapeake Bay, visitors will want to stay at the Vandiver Inn. This bed and breakfast is conveniently located within walking distance of many popular attractions. Guests will find the Concord Point Lighthouse within a 15-minute walk. The lighthouse is the oldest in Maryland that the public can visit, and the second-oldest in the state. It is situated within Concord Point Park, where guests can stroll along the surrounding trails while taking in views of the bay. Just north of the park, visitors will find Sailing Sur le Vent, a sailing charter offering casual daytime and sunset cruises that can last up to four hours. Just a little further north, guests can enjoy dining and shopping along St. John Street, which runs parallel to the river, making for exquisite evening meals by the water before returning home.
Chesapeake City

Chesapeake City does not sit along the bay but does enjoy a cozy spot along Back Creek. The Inn at the Canal is an ideal spot for a weekend getaway, offering a waterfront bed and breakfast that provides a lovely setting for meals or a drink by the water. Just around the corner, the Pell Gardens Park provides even closer access to the creek. Visitors during the summer can enjoy live performances at the summer concert series, while guests can enjoy views of ships sailing by throughout the year. Just steps away, you can also find the Chesapeake City Museum, which highlights the area's history through maps of the region, depictions of the city bridge, and artifacts brought by early settlers. And for those who love time outdoors, the Lums Pond State Park is just minutes away by car. Lums Pond is located in neighboring Delaware and is crisscrossed by park trails that are ideal for hiking and biking. Those who want to hit the water can head out on kayaks, while those interested in a thrilling afternoon can launch over the park on ziplines. This park is also ranked the best RV park in Delaware, making it a great option for spending a night on the grounds before heading back into town.
Bel Air

The town of Bel Air is a good choice for anyone who wants to spend time outdoors. A cluster of hotels sits minutes away along the highway, such as the Hampton Inn and Suites Edgewood. From there, it is just minutes away from Hartford Glen Park. The park includes a popular loop that circles Edgewood Reservoir. Those who want to get true waterside views may instead want to head south to nearby Flying Point Park, which sits along the Bush River. The park offers a stunning view of the waterfront, boat launches for those who wish to set sail, and a range of fun outdoor activities, including picnic areas, volleyball courts, and horseshoe pits. For those who love history and want to escape the sun, a trip to the Hay House may be in order. The Hay House is the oldest home in Bel Air, originally built in 1788 and now a living historic site. As a living historic site, there are special performances, including hearth cooking, and exhibits of antique clothing. Unique events are also held, such as candlelight walking tours in the winter.
Easton

Easton is the town of choice for those who want to enjoy a destination steeped in Colonial and Victorian-era architecture. You can see these buildings during one of Easton's many events. The renowned Waterfowl Festival invites residents and visitors to view paintings, sculptures, and photographs of waterfowl while enjoying food and drinks. One destination in town, the Academy Art Museum, was first erected in the 1820s and visually reflects the charming architecture of a bygone era. The museum is yet another fantastic destination for those who want to see paintings, pen and ink art, and other media on display. You can also indulge in an art class while you are there. While you are in the area, you might want to visit the Mary Jenkins House, which dates to 1783. This historic structure is the oldest in town and was home to the Women's Suffrage movement. And just minutes away, the Tidewater House keeps the spirit of the past alive, making it a fantastic place to spend the weekend. First constructed in 1874, this mansion is a testament to luxurious period architecture, boasting well-appointed rooms just minutes from downtown.
Leonardtown

Leonardtown sits along McIntosh Run, not far from Breton Bay, and it is a lovely place for those who enjoy a blend of history and the outdoors. The Inn at Leonardtown sits in the heart of town and serves as a boutique hotel with exquisite rooms, putting visitors just minutes from downtown. Not far away, the Old Jail Museum serves as the town's visitor center, where you can learn more about what to do in the area. However, you can also learn more about the Old Jail, first constructed in 1876, and discover the stories of the heroes of the Underground Railroad who were imprisoned there. You can also learn about the Leonardtown Trolley, an excellent way to explore First Friday in town. The trolley takes riders through the town's historic streets to visit art galleries, cafes, antique shops, and more. Just down the road, Leonardtown Wharf is popular among those who enjoy the water. The waterfront not only boasts incredible views but also offers a chance to set out on a canoe or kayak. You can also book sunset cruises with Fish the Bay Charters to enjoy happy hour on an authentic Chesapeake Bay boat.
Mount Airy

The town of Mount Airy is a destination for outdoor lovers, and the Budget Inn, located at the heart of town, will put you close to all the best outdoor spots. Not far away, you will find the Audrey Carroll Audubon Sanctuary, a 129-acre sanctuary made up of woodlands, wetlands, meadows, and streams. Visitors can walk the trails in search of field sparrows, warblers, woodpeckers, winter wrens, and more. On the opposite side of Mount Airy, the Gillis Falls Recreation Area features multi-use trails for hiking and biking. Visitors can expect their journey to take them through stream valleys and ridges, and to the notable site of an old summer camp that is no longer in use. And just 20 minutes away, Piney Run Park sits on the banks of Piney Run Lake. Guests can enjoy the 300-acre lake while walking five miles of trails or head out by boat to cast a line into the water.
New Market

New Market is a historic town in Maryland, known for its Historic District. You will want to stay at the Strawberry Inn, which has stood since 1973 and boasts a lovely garden perfect for enjoying the afternoon. A step outside takes you into the Historic District, where you can find structures such as the Historic Kemp House and the Historic Huff House. These nominees to the National Register of Historic Places are situated near the Gettysburg Campaign Marker, which describes the town's role as the Union Army camped here before moving on to nearby towns and ultimately, to Gettysburg. Close by, the Hill Chapel has stood since 1857 and sits along the historically preserved Main Street of town, where you can also find places to dine. If you want to relax in the sun, nearby New Market Plains Vineyards offers visitors a chance to enjoy a glass while listening to live music. For families with kids, Gaver Farms hosts seasonal events, including hayrides, a Christmas Café, and the Fall Fun Fest.
Maryland is a historic destination where armies from the Civil War passed through and refugees from the Underground Railroad escaped. It boasts incredible views at natural destinations like Concord Point Lighthouse, but also depicts its history in places such as the Old Jail Museum. If you are looking for a place to enjoy your weekend, consider visiting one of these 9 small towns for a combination of historic destinations, cultural events, and natural sights.