Aerial view of Oxford, Maryland on the Chesapeake Bay with clouds, water and shoreline.

11 Coolest Small Towns in Maryland for a Summer Vacation

Maryland might be one of the smallest states in the country, but this Mid-Atlantic gem has plenty of appeal, especially during the summer. In the west, the state is mountainous, overshadowed by the ancient Appalachian Mountains and regional offshoots, including the Allegheny Mountains. However, much of the state is defined by water, shaped by the Atlantic Ocean and the Chesapeake Bay, America’s largest estuary. One of America’s original thirteen colonies, Maryland is also one of the oldest states in the nation, meaning there are also plenty of historic destinations to explore. From outdoorsy mountain retreats to colonial-era hamlets to coastal villages renowned for fresh seafood, here are a few of the coolest small towns in Maryland for a summer getaway.

Havre de Grace

Aerial sunset panorama of Havre de Grace Maryland with orange sky and clouds reflecting on the Susquehanna River and the Chesapeake Bay
Havre de Grace, Maryland, with orange sky and clouds.

Situated at the confluence of the Chesapeake Bay and the Susquehanna River, Havre de Grace was named by General Marquis de Lafayette during America’s Revolutionary War, reportedly for its resemblance to the French town of Le Havre. A few years later, the hamlet was almost destroyed by British troops during the War of 1812, but fortunately, a few buildings survived.

Today, the town’s waterfront promenade features the Concord Point Lighthouse, the oldest continuously operated lighthouse in Maryland, originally constructed in 1827. Steps from the water, Havre de Grace’s walkable downtown boasts many cool restaurants and boutiques. As a nod to the town’s reputation as the "decoy capital of the world," the Havre de Grace Decoy Museum provides a glimpse into the region’s sporting history. Outside of town, Susquehanna State Park offers more than 15 miles of wooded trails for hikers and mountain bikers.


The Life of the Marsh Trail, Assateague Island National Seashore, Berlin, Maryland
The Life of the Marsh Trail, Berlin, Maryland.

Photogenic Berlin has appeared in two feature films, first providing the backdrop for the movie Runaway Bride in 1998 and later portraying the fictional village of Treegap for Tuck Everlasting in 2001. Berlin’s charming downtown certainly has plenty of cinematic appeal, with more than 47 structures listed on the National Register of Historic Places, including a number of well-preserved Federal and Victorian-era structures.

The walkable downtown is also loaded with restaurants, artisanal markets, galleries, and antique shops. For overnight getaways, the centrally-located Atlantic Hotel, built around 1895, offers rooms appointed with an authentically Victorian style. Berlin is also the perfect base for trips to the beach. Outside of town, the Assateague Island National Seashore is a 38,000-acre mosaic of maritime forest, tidal marsh, and seashore, roamed by wild horses. The adjacent Assateague State Park offers two miles of sandy beach, along with campsites beside the ocean.


Boats in the harbor of Oxford, Maryland.
Harbor of Oxford, Maryland.

Once a bustling colonial port, Oxford is among the oldest towns in Maryland, established around 1666. Rumored to have been the muse for James Michener’s novel Chesapeake, surrounding the photogenic town are multiple creeks and rivers, including the Tred Avon River.

Today, the waterside village is still home to the oldest privately operated ferry in the country, the Oxford-Bellevue Ferry, established in 1683. Visitors will discover the town’s 300-year history showcased at the Oxford Museum, the Water’s Edge Museum, and in the collection of historic homes still lining Oxford’s streets.


Bridges and mountains in the City of Cumberland, Maryland
Bridges in the City of Cumberland, Maryland.

Once known as the Gateway to the West, during the 1800s, the town of Cumberland was a hub for stagecoaches, and the starting point for the country’s first National Road (now known as US Route 40). After the arrival of the railroad, Cumberland remained one of Maryland’s top industrial towns until the early 1900s.

Today, Cumberland is anchored by an extensive Historic City Center studded with breweries, restaurants, and artisanal shops. The town also bookends the Western Maryland Scenic Railroad, a line linking Cumberland and Frostburg, offering a variety of scenic excursions. For outdoor lovers, Cumberland is the western terminus of the Chesapeake and Ohio Canal National Historic Park, a 184-mile multi-use trail extending to Washington, DC. The town also sits at the eastern end of the Great Allegheny Passage, a 150-mile rail-to-trail stretching to Pittsburgh.

St. Michaels

Aerial panorama of shipyard and lighthouse in St. Michaels harbor in Maryland in the Chesapeake Bay
St. Michaels harbor in Maryland in the Chesapeake Bay.

A colonial port pummeled by the British during the War of 1812, St. Michaels was once one of the Chesapeake Bay’s shipbuilding hubs, and a central player in the oyster industry. There are still plenty of reminders of the hamlet's maritime history, including the town’s extensive Historic District and the Chesapeake Bay Maritime Museum.

Many of the hamlet’s historic structures have been repurposed as art galleries, restaurants, and gift shops, most of them centrally located along the town’s main thoroughfare, North Talbot Street. For a unique overnight stay, the Wildset Hotel offers guest rooms housed in a collection of four thoughtfully-restored historic buildings, including a former schoolhouse, surrounded by leafy grounds. Outside of town, the Inn at Perry Cabin, a historic waterside resort anchored by a historic Greek-rival style estate, also famously appeared in the 2005 comedy Wedding Crashers.


Boats in the Harbor, Crisfield, Maryland
Harbor, Crisfield, Maryland.

Perched on Somers Cove, and offering easy access to the Tangier Sound, Crisfield was an epicenter of oyster harvesting during the late 1800s, and ground zero for the Chesapeake Bay’s bloody Oyster Wars. Today, the cool waterside town is still renowned for its seafood, and the perfect place to charter a boat for a day of fishing or sightseeing on the Bay. Crisfield is also a popular launch point for trips to Smith Island, the last inhabited archipelago in Maryland’s portion of the Bay. Just outside town, Janes Island State Park offers kayak rentals, a marina for fishing and crabbing, along with cabins and campsites for overnight visitors.

North Beach

Waterfront houses and boardwalk, in North Beach, Maryland.
Boardwalk in North Beach, Maryland.

Nestled along the western shore of the Chesapeake Bay, the waterside town of North Beach originated as a beachy getaway for residents of Washington, DC, and Baltimore. Today, the bayside hamlet is still a charming destination, especially for families. The town is anchored by a kid-friendly beach and boardwalk, paralleled by a paved bike trail. Further inland, the town offers a mix of souvenir shops, restaurants, and vacation cottages, as well as a handful of nature preserves for birdwatchers spread along the water. In the heart of town, the Bayside History Museum features exhibits on the region’s cultural and natural history.


CNB Bank office branch building, Hancock, Maryland
Downtown Hancock, Maryland. Image credit Alejandro Guzmani via Shutterstock

Nestled along the Potomac River in western Maryland, Hancock is among the oldest settlements in Maryland, even George Washington visited the hamlet. Once one of the state’s transportation centers, today, the town is a veritable trail junction, and the perfect getaway for cyclists. The town is traversed by the Chesapeake & Ohio Canal National Historic Park, threaded by a 184.5-mile crushed gravel trail extending from Washington, DC, to Cumberland, open to hikers and cyclists. The town is also situated along the Western Maryland Rail Trail, a 28-mile regional route stretching from Little Orleans to the Fort Frederick State Park just outside Big Pool. The town has plenty of creature comforts for cyclists, including trailside lodging, artisanal markets, and restaurants.


A red covered bridge, Loys Station Covered Bridge in Thurmont Maryland
Loys Station Covered Bridge in Thurmont, Maryland.

An idyllic base for exploring the Catoctin Mountains, Thurmont is an inviting destination year-round. Outside of town, there are orchards and vineyards, including Links Bridge Vineyards and the Catoctin Breeze Vineyard. The town is also surrounded by a trio of photogenic covered bridges, the Loy’s Station Bridge, the Roddy Road Bridge, and the Utica Mills Bridge. For more fresh air adventure, Cunningham Falls State Park features many options for cooling down, with hiking trails, and a lake for swimming and boating, and campsites and cabins. However, perhaps the region’s most famous attraction is trail-threaded Catoctin Mountain Park, renowned as the home to Camp David, a presidential retreat for almost a century.

Chesapeake City

View of Chesapeake City from the Chesapeake City Bridge, Maryland.
Chesapeake City from the Chesapeake City Bridge, Maryland.

Anchored by a historic district studded with buildings from the mid-19th century, Chesapeake City is the only town in Maryland situated along a functioning commercial canal, the Chesapeake and Delaware Canal, now a link in the Intracoastal Waterway. Completed in 1829, the canal connected markets in Baltimore and Philadelphia, and put Chesapeake City on the map. The largest remaining portion of the original town is still situated along the southern side of the canal.

Beyond the atmospheric architecture, the Chesapeake City Museum also showcases the town’s engaging history, and many of the town's historic buildings have been reinvented as one-of-a-kind boutiques, inns, and restaurants. In addition, there are more than a dozen wineries located less than an hour from Chesapeake City, all part of the Chesapeake Wine Trail. For outdoorsy visitors, the 1.8-mile Ben Cardin C & D Recreational Trail begins in town and extends to the Delaware border and connects with the 12.4-mile Michael Castle Trail. Outside Chesapeake City, Elk Neck State Park spreads over a peninsula bounded by the Chesapeake Bay and Elk River, offering swimming beaches, hiking trails, campsites, and cabins.

Rock Hall

A middle aged caucasian couple is sitting on a bench by the beach. They have their identical bikes parked next to them. Woman gives the man a pat on the back, Rock Hall, Maryland
Sitting by the waterfront in Rock Hall, Maryland.

A historic fishing and crabbing village established in 1706, Rock Hall is a serene summer getaway. Nestled along the eastern shore of the Chesapeake Bay, this cool town is inextricably connected to the massive estuary. Fresh seafood harvested from the Bay is available at the town’s waterfront bars and cafes. So it’s easy to catch an epic sunset during dinner, and, it’s easy for visitors to get on the water too.

The town offers a swimming beach at Ferry Park, and paddlers can launch kayaks or stand-up paddleboards from the beach, the Rock Hall harbor, or opt to explore the waters of Swan Creek. There are also a variety of operators offering charters for sightseeing tours or fishing trips departing from the town’s harbor, along with two sailing schools for aspiring mariners. South of town, the Eastern Neck National Wildlife Refuge is a hotspot for birdlife, offering six hiking trails, kayak launches, and exhibits on the region’s ecology.

From the Appalachian Mountains to the Atlantic Ocean, Maryland has a lot to offer travelers, especially during the summer. With an abundance of historic sites, natural wonders, fresh local seafood, and miles and miles of coastline along the Atlantic Ocean and the Chesapeake Bay, there are plenty of reasons to visit one of these coolest small towns in Maryland.

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