2025's 9 Best Small Towns To Visit In Maryland
Maryland's allure comes from its diverse natural landscapes, noteworthy cultural contributions, and rich historical heritage, making it one of the most sought-after destinations on the East Coast. Between the Blue Ridge Mountains to the west and the Atlantic Ocean to the east, you'll come across an endless list of fine destinations where you can spend a vacation.
But beyond the well-known cities and coastal hubs lies a quieter charm, centered around the state’s small towns. These hidden gems are packed with unique character, scenic beauty, and welcoming communities, promising a gratifying tourist experience. Whether you're craving waterfront tranquility in Oakland or a cozy mountain retreat in Thurmont, the best small towns to visit in Maryland guarantee unforgettable experiences without the crowds.
Boonsboro
This charming village in the foothills of South Mountain offers boundless outdoor opportunities across its beautiful natural spaces. Boonsboro is home to Greenbrier State Park, a popular recreational hub bordering a 42-acre man-made lake. Hikers, swimmers, picnickers, boaters, hunters, and canoers alike often converge here to relish the fresh air. With the famous Appalachian Trail cutting through Boonsboro, hikers can look forward to a refreshing trek in South Mountain State Park, with 360-degree panoramas to soak in at High Rock and Weverton Cliffs.
But the town delivers more than outdoor adventure. Along its Main Street, you'll come across the Boonsborough Museum of History, which brings local history to life with a catalog of glassware, weapons, ceramics, and other artifacts. Also, souvenir geeks can invest in a cute vintage treasure at Boonsboro Antiques for their memories.
Oakland
Oakland is a popular escape for nature lovers in Garrett County, situated near Deep Creek Lake and surrounded by breathtaking scenery at every turn. Swallow Falls State Park is the epitome of the town's outdoor splendor, teeming with exquisite waterfalls, mature hemlock trees, and rugged hiking trails. This is an invitation for adventurers to explore a beautiful jungle, with the highlight being a 53-foot spectacle that is Swallow Falls. Meanwhile, Alpaca Acres Farm and Fun presents a family-friendly reason to be outside, with a chance to pet cute alpacas in a serene farm set in the mountains of Western Maryland.
The town preserves its enduring railway heritage at the Oakland B & O Railroad Museum, whose exhibits highlight the contributions of the railroad to the area's growth through the years. Also, guests will relish getting to know the locals and supporting their businesses at the Mountain Fresh Farmers Market.
Havre De Grace
Whether you appreciate natural beauty, historical heritage, or modern entertainment, this Harford County town delivers it all, and then some, making for one of the best small towns to visit in Maryland. Havre de Grace's historic downtown district harbors treasures like the Havre de Grace Maritime Museum, which portrays the longstanding heritage of crabbing, fishing, and sailing in the region. This is possible due to the town's location at the confluence of the Chesapeake Bay and the Susquehanna River, a magical scene that you can admire from the delightful Havre de Grace Promenade.
Millard Tydings Memorial Park is where residents chill out and enjoy a cool atmosphere during their free time, perfect for lazy walks and nonchalant picnics with family. Finally, the Cultural Center at the Opera House entertains guests for a mix of classic and contemporary performances, featuring dance, film, plays, live music, and more.
Frostburg
Home to Frostburg State University, this charming village enjoys a bubbly arts and culture scene and lies in the beautiful mountains of Western Maryland. Several tourists come for the cultural experience, which they find by browsing traditional art pieces and antiques at Mountain City Traditional Arts or watching an electrifying dance routine at the Mountain City Center for the Arts. A unique history lesson awaits visitors to the Thrasher Carriage Museum. The venue exhibits dozens of vintage horse-drawn carriages, sleighs, wagons, and other forms of vintage vehicles chronicling the nature of transportation in the late 19th century and early 20th century.
However, you can get a deep dive into the region's broad heritage at the Frostburg Museum, whose displays represent everything from coal mining and military to music and everyday life. Frostburg's mountain appeal comes into perspective during a scenic rail bike tour courtesy of Tracks and Yaks, which weaves through the tranquil countryside.
Saint Michaels
This Chesapeake Bay community charms travelers with its terrific waterfront views, rich crabbing culture, and fun adventures on the water. First-timers can ride the St. Michaels Harbor Shuttle for a unique perspective of the town's beauty. This 30-minute to hour-long cruise explores the shoreline while delivering unmissable sightseeing opportunities. The Chesapeake Bay Maritime Museum preserves a library of old artifacts, documents, and even relics of vintage vessels to highlight the region's seafaring heritage.
Downtown St. Michaels boasts a vibrant scene with a mix of restaurants, bars, pubs, and local businesses. This is the perfect place to try out the famous Chesapeake Bay cuisine, with mouth-watering crab and lobster dishes awaiting at Foxy's Harbor Grille, before washing it down with craft beer at Eastern Shore Brewing.
Thurmont
Thurmont's distinct appeal comes from its spectacular mountainous surroundings, endless outdoor adventures, and a string of historic covered bridges. The town's motto, "Gateway to the Mountains," sets the stage for exciting pursuits in its vast wilderness area. These range from rock climbing and hiking to camping and hunting in the 5,000-acre Catoctin Mountain State Park. But if you don't want to strain your body, you can take an easier challenge on the 18 holes of Maple Run Golf for a low-key session with peers.
Thurmont’s covered bridges are a testament to impressive old-world engineering and craftsmanship. The Historic Utica Covered Bridge is an example, built in the 1830s, yet it maintains its structural integrity. Lastly, don't miss out on an opportunity to make a furry friend while checking diverse exotic species at the Catoctin Wildlife Preserve.
Ocean City
Ocean City is a popular summer escape on the shores of the Atlantic Ocean, loved for its soothing combination of sun, sea, and sand to deliver the perfect vacation. Many of the approximately 8 million annual visitors to the town come for the beaches, and Ocean City Beach is one of the best spots. This is where beachcombers, sunbathers, picnickers, and sightseers converge to revel in the serene environment. The historic Ocean City Boardwalk balances nostalgia with family-friendly fun, calling families to make the most of shopping, dining, and carnival fun.
Visitors can also explore some of the community's heritage at the Ocean City Life-Saving Museum, whose quirky exhibits highlight local sea rescues. Alternatively, a fishing or sightseeing cruise courtesy of West OC Watersports is an awesome pursuit during your stay in Ocean City.
Cumberland
Cumberland rests in the foothills of the Appalachian Mountains on Maryland's western corner, known for its pastoral allure that is complemented by a historic and walk-friendly downtown area. A slow-paced tour on the Western Maryland Scenic Railroad provides front-row views of the town's stunning wilderness as the train weaves through the Allegheny Mountains. If you are not riding the train, you can get up close with nature at Constitution Park, which offers walking trails, playgrounds, and picnic pavilions.
Back in downtown, the Gordon-Roberts House provides a glimpse into the Victorian era inside a 3-story mansion furnished with period artifacts and exhibits. Also, you can peruse a collection of pieces by local and regional artists at the Allegany Arts Council.
Crisfield
Crisfield is an adorable fishing village along the Chesapeake Bay that lures vacationers with its small-town charm, stupefying water views, and delicious local cuisine. It offers excellent tours on the water, with many local outfitters waiting at Somers Cove Marina to take guests on unforgettable sightseeing excursions. The Crisfield Arts and Entertainment District is the heart and soul of the community, hosting a mix of artists, creators, crafters, performers, and musicians that breathe life into the downtown district.
Historians can explore interesting backstories at the J Millard Tawes Historical Museum, which highlights various aspects of Crisfield's history, including shipbuilding, crabbing, oystering, and more. Finally, stop by Fisherman's Grille and savor scrumptious seafood favorites to wrap up your tour of Crisfield.
Final Thought
From the mountain serenity of Cumberland to the waterfront charm of Havre de Grace, the best small towns to visit in Maryland offer a refreshing escape filled with history, natural beauty, and local flavor in the United States. Whether you're wandering scenic trails or enjoying coastal sunsets, these towns embody the spirit of Maryland in unforgettable ways. Together, they expose tourists to the magic of small-town life while providing the perfect getaway from the endless hustle and bustle of the city.
