9 Best Small Towns In Maryland For A Crowd-Free Summer

Across Maryland, there are plenty of towns where summer feels a little slower and the crowds stay away. Western Maryland’s Appalachian Mountains and old-growth forests offer quiet trails, native wildlife, and scenic landscapes, while Eastern Shore and Chesapeake Bay communities lean into their waterways, marshes, and coastal charm. In Boonsboro, the Appalachian Trail runs nearby, making the town a familiar stop for hikers looking to rest and resupply. Farther south, Leonardtown brings a waterfront setting along the Potomac River. These nine towns show there’s no one way to enjoy a Maryland summer.

Oakland

Oakland is a quiet, Appalachian Mountain town that combines natural beauty with railroad history. Surrounded by forests, rivers, and mountains, the town's mild summer temperatures support activities like hiking and fishing. Swallow Falls State Park is a 257-acre preserve with trails through old-growth forest and along the Youghiogheny River. Muddy Creek Falls, the park’s main attraction, is one of Maryland’s tallest waterfalls.

Nearby, Herrington Manor State Park offers swimming, camping, and canoeing. The downtown features a local museum, B&O Railroad Station Museum, in a restored Victorian train station. It preserves local railroad history with artifacts and photographs. Its outdoor exhibits include an engine and a caboose.

Leonardtown

In southern Maryland, Leonardtown sits on Breton Bay near the Potomac River, with waterfront parks and opportunities for outdoor recreation. The walkable downtown area has locally owned shops, including used bookstores and antique shops. The town's Arts and Entertainment District, a designated arts district, has art galleries and several murals across town.

Leonardtown Wharf Park features walkways, a fishing pier, and a kayak launch. Tudor Hall adds another historic stop near the waterfront area. The Port of Leonardtown Winery hosts live music and scenic views.

Rock Hall

Rock Hall, on Maryland’s Upper Eastern Shore, is a coastal community with waterfront restaurants and harbor views. Centered around Rock Hall Harbor, it is well known for sailing and recreational boating, with numerous marinas providing access to the Bay.

The Eastern Neck National Wildlife Refuge spans more than 2,000 acres on the Chester River and the Chesapeake Bay. Habitats include marshes, upland forests, and grassland. With more than 240 bird species seen in the area, it is an Audubon Society-designated Important Bird Area. The Waterman’s Museum nearby, celebrates the oystering and crabbing traditions of Chesapeake Bay watermen.

Berlin

Berlin has a walkable historic district lined with galleries and boutiques in restored Victorian buildings, many on the National Register of Historic Places. Fans may recognize Berlin as the filming site for the 1999 movie "Runaway Bride," starring Julia Roberts and Richard Gere, as well as the 2002 film "Tuck Everlasting."

Downtown Berlin hosts local musuems such as, the Mermaid Museum and the Ghost Museum, each reflecting the town's offbeat side. Meanwhile, the Calvin B. Taylor Museum re-tells Berlin's past through exhibits on African American history, antique textiles, and the people who shaped the community. At 62 acres, Heron Park has ponds, woods, and wetland edges that draw waterfowl, herons, raptors, and migrating songbirds.

Crisfield

Set on Maryland’s Eastern Shore at Tangier Sound, Crisfield is a working waterfront community built on Maryland blue crab and oyster harvesting. The Chesapeake Bay shapes daily life, earning the town the nickname, Seafood Capital of the World. Regular ferry service connects Crisfield with Smith Island and Tangier Island, making the town an important gateway to two of the bay's most remote communities.

At Janes Island State Park, a 2,900-acre preserve, you can fish and kayak through more than 30 miles of water trails. The Crisfield Heritage Foundation Museum preserves exhibits and displays about the town's maritime history. Somers Cove Marina gives boaters direct access to Tangier Sound and the lower Chesapeake Bay.

Brunswick

Brunswick is near the Virginia and West Virginia borders in west-central Maryland, along the north bank of the Potomac River. The town was built on canal and railroad history, as a trading post on the Chesapeake and Ohio Canal and a railroad industry hub with the Baltimore and Ohio Railroad. Originally named Berlin, the name was changed to distinguish it from the Berlin on the Eastern Shore. Brunswick was chosen because of the large number of railroad workers from Brunswick, Germany.

The Brunswick Heritage Museum has a 1,700-square-foot model railroad and other exhibits that preserve the impact that the C&O Canal and the B&O Railroad had on the town. Built in 1832, the Catoctin Creek Aqueduct towpaths are nearby, offering hiking and bicycling paths, as well as opportunities to learn about the history of the aqueducts. These “water bridges” transported canal boats over the small creeks that ran to the Potomac River.

Havre de Grace

Havre de Grace is set where the Susquehanna River meets the Upper Chesapeake Bay. Despite its proximity to Interstate 95, it maintains a residential rather than commercialized hub. Its walkable main street has boutique shops and family-owned seafood restaurants. The Havre de Grace Decoy Museum highlights the Bay’s decoy-carving traditions, sharing examples of its status as the Decoy Capital of the World.

On the Susquehanna, the Havre de Grace Promenade spans from Millard Tydings Park to Concord Point Park. Blue herons and ospreys can sometimes be seen on the waterfront. At the southern end of the ¾-mile boardwalk, the 1827 Concord Point Lighthouse is one of Maryland’s oldest publicly accessible lighthouses. A museum is within the light keeper’s house. The Susquehanna State Park has forest trails and a boat launch to get out on the river or the Bay.

Boonsboro

In central Maryland at the base of South Mountain, Boonsboro is known for its natural landmarks and uncrowded setting. The town has a combination of American history and outdoor recreational opportunities. Boonsboro serves as an access point for hikers taking on the nearby Appalachian Trail, which follows the ridgeline of South Mountain. It is one of Maryland’s first designated Appalachian Trail Communities and features gear outfitters, shuttle services, and other resources for hikers.

On South Mountain, Washington Monument State Park features the nation’s first monument dedicated to George Washington, a stone tower erected in 1827. Hawks and eagles can often be seen in the area. The 40-mile-long South Mountain State Park has hiking trails and waterfalls.

Thurmont

Thurmont is a mountain town near the Pennsylvania border with forested parks and covered bridges. Located at the entrance to the Appalachian region, it has outdoor activities and nature watching. One of three covered bridges in town, the Historic Roddy Road Covered Bridge is a single-span bridge crossing Owen’s Creek. Built around 1856, it is 40 feet long and 16 feet wide.

With 25 miles of scenic hiking trails, Catoctin Mountain Park is a hardwood forest on the eastern edge of the Blue Ridge Mountains. Native plants and threatened species can sometimes be seen. Catoctin Wildlife Preserve is a habitat for monkeys, leopards, birds, and other animals.

Maryland Towns Where Crowds Are Few

Maryland’s mountain towns and coastal communities offer scenic landscapes and natural landmarks without the heavy crowds. On the Eastern Shore, wildlife defines destinations such as Crisfield's Janes Island State Park and Rock Hall, where Eastern Neck National Wildlife Refuge serves as a habitat for migratory birds. Other towns are distinguished by the waters of the Chesapeake Bay and the hills and valleys of the Allegheny and Catoctin Mountains. Despite their varied landscapes, these Maryland towns share friendly communities that makes them suitable for short or extended visits.