8 Easygoing Small Towns in Maryland
Maryland is known for its prime real estate on the Chesapeake Bay and its abundance of seafood, especially the world-famous blue crab. Many of its small towns are laid-back retreats with a wealth of maritime and colonial history to explore, parks and landmarks to visit, and local restaurants and shops that serve unique fare and products not found in major cities. Here, you will find museums dedicated to ghosts and mermaids, a replica of the very first tall ship that brought British colonists to the state, and access to both the Atlantic Ocean and the Appalachian Mountains. These easygoing sweet spots are a must-visit for anyone looking to explore something new and in need of a bit of a breather, and they deserve a closer look on your next Maryland travel itinerary.
Chestertown
On the banks of the Chester River is Chestertown, a walkable community with a rich history and plenty of opportunities for recreation on the water. The High Street Town Dock is the spot for public events and is home to the Chester River Packet, offering both public and private cruises on the river from April through November. The Chestertown Marina provides a place for boat owners and renters to explore the river, a place to fuel up, launch their boats, go on fishing trips, and enjoy a sunny day on the water, all steps from shops and cafes.
Downtown, the Garfield Center for the Arts at the Prince Theatre is the place to enjoy a local play or musical, not to mention annual events like the Chestertown Jazz Festival and the Chestertown Tea Party Festival. Across from the theater is the White Swan Tavern, a historic inn in the heart of downtown. The suites are well-appointed and historic, and provide the perfect place to gather for weddings and reunions, which gives guests access to everything downtown Chestertown has to offer.
Berlin
The town of Berlin has incredibly fun and unique museums in the heart of downtown. For starters, at the Mermaid Museum, guests can learn more about the iconic fictional beings through engaging, interactive exhibits that invoke all the senses. The Ghost Museum is within walking distance of the Mermaid Museum, and its mission is to entertain and educate the curious on the history of ghosts, with stories of sightings and the folklore behind them.
The rest of downtown is full of wonderful restaurants, shops, and hotels that give visitors and residents alike a warm welcome. The Atlantic Hotel is in the center of the action, providing guest rooms and junior suites. It also hosts special events and is home to a fabulous bistro and bar for tasty bites and cocktails or a craft beer. Just up the street is CounterClox and the Vault at 104, a local restaurant serving up memorable meals, excellent drinks, and live music in an upbeat and modern setting.
Easton
In Easton, historical charm meets a vibrant arts scene. The Academy Art Museum is a cultural hub with over 1,700 pieces on display that hosts art education classes and workshops, as well as community events and classical music series. The Avalon Theatre is a historic art deco theater in downtown that also hosts cultural events, musicals, plays, and much more.
Across from the theater is the Tidewater Inn, a luxury boutique hotel providing a breathtaking escape. The hotel has premier guest rooms and suites, and invites guests to unwind in Hunter's Tavern for an authentic Eastern Shore meal. Beyond the hotel, the Scossa Restaurant and Lounge serves fine Northern Italian dining from a diverse, seasonal menu.
Leonardtown
Near Breton Bay on the southern end of the state is Leonardtown. Leonardtown Wharf Park gives people spectacular views of the bay and boat launches for those wanting to get out on the water, as well as a boardwalk, playground, and park for all to enjoy. You'll find wonderful small museums, restaurants, and shops along Washington Street. The Old Jail was built and used by the oldest sheriff's department in the country, operating from 1876 until 1945. Today, it's home to a museum and visitor center. Sweetbay Restaurant and Bar is right in the heart of downtown, serving gourmet meals in an upscale setting.
St. Mary's City
Just down the road, St. Mary's City was the first European settlement in the state and Maryland's original capital. A great spot for an introduction to the town and its history is at the Maryland Dove, a replica of the tall ship that brought the first British expedition to Maryland in the 17th century. The Historic St. Mary's City itself is essentially a living museum that preserves and protects the archaeological and historic record of the state and country's early days, with historic buildings on display for visitors to tour, and reenactments of events and everyday colonial life.
St. Mary's City is also home to St. Mary's College of Maryland, a public liberal arts college in the community, which features the Nancy R. & Norton T. Dodge Performing Arts Center, where visitors, residents, and students can enjoy world-class performances in a 700-seat auditorium or a 125-seat recital hall, and take music classes within the facility.
Havre de Grace
At the mouth of the Susquehanna River and the Chesapeake Bay is the easygoing city of Havre de Grace. Given its maritime setting, it should come as no surprise that there are several marinas in town. Tidewater Marina, Havre de Grace Marina at the Log Pond, and Penns Marina at Heron offer boat storage and fueling, all within walking distance of downtown. The Havre de Grace Maritime Museum honors the heritage, culture, and industries that support life on the Susquehanna River and the Chesapeake Bay, and it is next to Concord Point Park, where people can enjoy scenic views of the waterfront and visit the state's second-oldest lighthouse and its Keeper's House Museum.
Another unique museum to visit in town is the Havre de Grace Decoy Museum, which goes into the history of duck decoys in hunting and fishing. To toast a day well spent, head to Market Street Brewery, a nano-brewery and event space with seats overlooking the Susquehanna River and local craft beers.
Boonsboro
Boonsboro is full of historic charm, thanks to its role in the US Civil War, has a walkable downtown, and is located in proximity to natural wonders and trails in the Appalachian Mountains. The town boasts three museums to satisfy history buffs. The Boonsboro Museum of History has artifacts from the Civil War on display and rare books from the era, the National Road Museum is dedicated to the history of the nation's first federally funded highway in 1806, and the Boonsboro Trolley Museum, housed in the town's trolley station from 1902 until 1938, displays trolley artifacts and photos.
In the heart of downtown is the Inn BoonsBoro, a boutique hotel giving visitors access to the museums, restaurants, and shops just steps away. The rooms are lovely and relaxing, and guests can enjoy a two-course breakfast in the morning. Just outside of town is the Devil's Backbone County Park, a scenic retreat where people can enjoy a walk on the footbridge with playgrounds for families, picnic tables, and grills for gatherings.
Thurmont
The laid-back town of Thurmont is considered a gateway to the Catoctin Mountains, home to numerous trails, such as the Wolf Rock and Chimney Rock Trail, a moderately rugged 3.8-mile loop that leads to outstanding vistas. Another popular but challenging hike is the Catoctin Mountain Extended Loop, an 8.8-mile trail rewarding visitors with breathtaking views of the landscape, geological features, and local wildlife.
Main Street and Water Street meet in the center of downtown, which features unique shops and local eateries. The 10Tavern is a great family-friendly spot to fuel up before or after a day exploring Thurmont, and it also hosts trivia nights, happy hours, and other local events for the community to enjoy. While in town, remember to keep an eye out for any presidential sightings, as Thurmont is also the home of the presidential retreat and Naval base, Camp David.
Life is Easygoing in the Free State
From towns like Havre de Grace and Chestertown, providing access to the water, to places like St. Mary's City and Leonardtown, showcasing the state's history, there's something special about visiting these delightful, easygoing communities that you won't find in larger cities. These towns inspire whimsical and local adventures, and they provide ideal backdrops for a weekend escape or quick getaway.
