11 Best Small Towns in Maryland for Outdoor Enthusiasts

Maryland is one of the most historic states in the US, with a rich colonial heritage. However, the state's abundant outdoor scenery shares the spotlight with its historic allure. As a Mid-Atlantic state, most of its small towns are perched on the gorgeous coastlines of the Atlantic Ocean and Chesapeake Bay. Thus, they offer endless scenic destinations for outdoor enthusiasts and those looking to break free from a life of seclusion. Beaches, lakes, state parks, forests, and sensational downtowns await every explorer in these towns, and fond memories are almost guaranteed.

Chesapeake City

Chesapeake City rests along the Chesapeake and Delaware Canal in Cecil County and features a population of less than 800. While it may be small in terms of population, this town is big on outdoor charm, with a city dock where boat lovers can explore the water channel or admire its views from walking around the harbor.

Visitors can also learn about its history and how the Canal created the city at the Chesapeake & Delaware Canal Museum. Next, visitors can hike on the Ben Cardin Recreational Trail, a waterfront trail along the channel, or rent a boat to soak in the sights and sounds of nature on the canal. More adventures, such as kayaking, canoeing, fishing, and paddling, await unsatisfied outdoor buffs at the nearby Bohemia River State Park.

Chestertown

Chestertown is a gorgeous little town in Kent County with a rich history, impressive natural scenery, and lots of exciting activities for outdoor enthusiasts. One of the most popular parks in town, Wilmer Park, runs along the Chester River and offers opportunities for kayaking, hiking, picnicking, and bird-watching. For more adventures, visitors can go on a shopping spree in the historic district, where local boutiques and shops are lined up waiting to offer the best crafts. While in the area, check out historical and art attractions, including the Bordley History Center, Massoni Art Gallery, and Garfield Center for the Arts.

Cumberland

Cumberland is a central business and commercial hub for western Maryland, but that does not stand in the way of its inviting outdoor charm. The Potomac River flows through the town and is home to the Chesapeake and Ohio Canal. This canal connects Washington, DC, to Cumberland, serving as a recreational spot for fishing, boating, and hiking.

Cumberland is also home to Wills Creek and the Cumberland Narrows (Lover's Leap) - a water gap that slices through Wills Mountain, presenting postcard-perfect views of Wills and Haystack Mountains. Don't miss the nearby 3,118-foot-long Paw Paw Tunnel along the Chesapeake and Ohio Canal, an engineering feat named after the paw paw trees on its ridges. 

Berlin

Berlin is a small town in Maryland that flaunts irresistible touristy appeal and a bustling outdoor scene. The downtown area of this town is unforgettable, with many Victorian-era buildings, shops, restaurants, and antique stores to explore. To begin, visitors can walk along the town’s downtown area on the National Register of Historic Places with a camera to capture the postcard views and appreciate a 19th-century ambiance. Afterward, head to Assateague State Park to unwind at its gorgeous powdery sand beaches. The park, part of the Assateague National Seashore, is also home to many seabirds and wild horses, among other wild and marine animals.

Crisfield

Crisfield is a charming fishing town in Tangier Sound and a scenic outdoor destination for those who love beaches, islands, and seafood. Visitors will be met with Wellington Beach, Brick Kiln Beach, and lively outdoor hotspots for sunbathing, picnicking, and hunting crabs. In addition, the pristine Janes Island State Park is adjacent to the town and features 30 miles of water trails through salt marshes.

Visitors can enjoy views of the salt marshes by paddling a canoe to its 7-mile-long unspoiled beach where there are opportunities to spot crabs, swim, enjoy picnics, and even camp. For more adventures here, take a boat cruise to and from the neighboring Smith and Tangier Islands.

Ocean City

Ocean City is a gorgeous town in Worcester County and a haven for outdoor activities. This resort town flaunts a gorgeous coastline that attracts tourists from all over the Mid-Atlantic and beyond. In summer, the town's population of around 6,800 rises to 300,000 and becomes the second most populated municipality in Maryland, tailing behind Baltimore.

The highlight of a visit to this town is the Ocean City Beach and Pier, where visitors can sunbathe, promenade, play on the sand, catch the sunset, and swim. Stroll along its iconic boardwalk, home to several shops, arcades, restaurants, and two amusement parks for outdoor recreation. Trimper, one of the parks here, houses the oldest running carousels in the US and is called "The Pride of the Boardwalk."

Oakland

Oakland was once a bustling railroad town and still has occasional train transits. Not a train lover? The town is just a few miles from the Potomac River's source, a thrilling hub for boating, fishing, and sightseeing. In addition, Swallow Falls State Park is just nine miles from town, and visitors will enjoy some of the most stunning views of Maryland's nature. While in Swallow Falls Park, be sure to hike around to catch views of the charming 53-foot waterfall, the highest free-falling waterfall in the state. Afterward, stop by the 3rd Street Diner in town, where various American fares await to offer maximum satisfaction. 

Hampstead

Hampstead was a former British settlement that rose to become an agricultural melting pot in Carroll County. Today, it is a quaint town that outdoor lovers would be delighted to call their home as it features so many natural attractions like Cascade Lake, where one can swim, boat, or just sit by the shores and admire the views while munching a snack. Pretty Boy Reservoir Park is another incredible natural attraction in this town, featuring a scenic dam with a 2.6-mile loop trail for hiking. Visitors can also fish on the dam, admire its lush scenery, and spot diverse birds. Leister Park is another excellent place in town for hiking trails and relaxing spots for picnics.

Havre De Grace

Havre De Grace is a small, charming town on the shores of the beautiful Susquehanna River and Chesapeake Bay. On the river, outdoor enthusiasts are welcome to enjoy exciting activities like swimming, boating, and fishing. Additionally, the river is part of the Susquehanna State Park, where plenty of hiking trails exist.

Visitors who prefer laid-back activities can walk on the Havre De Grace Promenade, which offers scenic river views and leads to the 19th century Concord Point Lighthouse, which serves as a museum, while its top offers charming river views. Alternatively, walk across the Thomas Hatem Memorial Bridge to admire sailboats on the glistening waters and visit Millard Tydings Memorial Park to enjoy picnics and scenic river views.

Boonsboro

Boonsboro is the perfect example of what an outdoor haven should look like. Perched at the foot of the South Mountain, lush forest areas characterize this town, and imposing mountain views give it a paradisaic scenery. Boonsboro is home to the Crystal Grottoes, the state's only show cave, where adventurers can tour its interiors to behold magnificent stalactites and stalagmites. The town also features Greenbrier State Park, which offers many activities, from mountain biking to fishing, swimming, boating, picnicking, and camping. For more adventures, visitors can head over to the park’s 42-acre artificial lake to swim and promenade around its small 1,000-foot beach.

For hikers, Greenbrier State Park has a lot of trails, such as Yellow Trail, Bartman Hill Trail, and Water Tank Trail, which range between 0.4 to 4 miles in length. For something unique, visitors to this town can check out the Washington State Monument Park, which features a foot tower dedicated to George Washington and offers activities like picnicking and hiking.

Thurmont

Thurmont is a gorgeous town whose motto reads "Gateway to the Mountains." Visitors will be met with attractions like Cunningham State Falls Park, which offers hiking trails to the state's largest cascading waterfall. Adjacent to the Falls Park is the Catoctin Mountain Park, which boasts over 25 miles of scenic hiking trails that offer enchanting mountain views. This park is also home to the famous Camp David, a retreat for most US presidents. Visitors can also walk its tree-shaded streets in the downtown area, patronize the shops and restaurants, and relate with locals. The town hosts an annual Colorfest Arts and Crafts Festival in autumn that showcases artworks and local crafts.

Away from Baltimore, the largest and most famous city, Maryland is lavish with enchanting small towns that boast incredible outdoor allure and many fun things to do. Whether visitors want to spend their time relaxing outdoors or engaging in thrilling activities, these towns have something to satisfy every traveler across all seasons.