10 Cutest Small Towns In Maryland
Defined by sweeping coastlines along the Atlantic Ocean, rugged wildernesses in the foothills of mountain ranges, and iconic historical markers throughout its territory, Maryland captures the perfect balance between rich history and natural splendor. This mid-Atlantic destination blends the sophistication of urban life with the serenity of rural landscapes, offering endless discoveries beyond the crowded streets of Baltimore. The Old Line State is replete with endearing small towns where you will discover the true charm of the region.
However, some of these hidden gems leave a lasting impression with their majestic natural surroundings, unique vintage architecture, and colorful traditions, compelling first-timers to schedule a return date. From the ever lively Main Street atmosphere in Berlin to the picturesque oceanfront of Ocean City, here are the cutest small towns in Maryland for 2025.
Hyattsville
Hyattsville is a laid-back suburb of Washington, DC, boasting a deep connection with nature and the arts. The town hosts more than a dozen parks to ensure ample space for outdoor recreation. From Burlington Park to Centennial Park, guests can take advantage of picnic areas, walking trails, and playgrounds to commune with Mother Nature. The Pyramid Atlantic Art Center showcases Hyattsville's artsy side. This lovely venue welcomes newcomers to workshops, exhibitions, and classes on papermaking, printmaking, and demonstrations designed to inspire the community.
Meanwhile, the Mall at Prince George's is a hub for shopping and dining in Hyattsville. It is riddled with brand retailers, dining destinations, and entertainment venues awaiting discovery. Another great way to stay entertained is to connect with local patrons over craft beer at Streetcar 82 Brewing Company.
Elkton
This historic community in Cecil County is renowned for its stunning open spaces and vibrant downtown area, featuring diverse attractions. Elkton traces its fascinating beginnings back to the late 17th century, and the Historical Society of Cecil County is responsible for sharing the past with visitors. A tour of the facility reveals a genealogical library and a military museum that chronicle various historical aspects.
Those seeking to connect with the arts can visit the Cecil County Arts Council, where a vibrant community of creatives comes together to inspire one another through exhibitions, performances, workshops, and more. Elkton offers a serene outdoor escape at Elk River Park, which spoils vacationers with unprecedented vistas of the water. The area is a favorite among picnickers, boaters, and anglers, spanning 68 acres of marshland habitat.
Havre De Grace
Between the vintage architecture decorating its historic district and the dramatic collision of the Chesapeake Bay and the Susquehanna River waters, Havre de Grace is one of the cutest small towns in Maryland to visit. Nature photographers love to position themselves along the Havre de Grace Promenade to capture the beauty of the two waterways in the town. However, ardent adventurers venture deeper inland into the open wilderness of the Susquehanna State Park.
Punctuated by dense forest cover and a rugged topography along the Susquehanna River, this natural recreation center accommodates fishermen, hikers, campers, and mountain bikers. Downtown Havre de Grace is home to a rich collection of museums interpreting the town's dynamic history. The Havre de Grace Maritime Museum stores resourceful documents and artifacts that explain the region's rich nautical history, which is complemented by the unmissable Friends-Concord Point Lighthouse.
Oxford
Oxford is a waterfront village in Talbot County, boasting small-town charm rooted in its colonial heritage. The community's heritage dates back to the 17th century, when it was founded, and first-timers can immerse themselves in its captivating past at the Oxford Museum. Exhibited within the facility is a diverse collection of vintage photographs, paintings, boat-building equipment, furniture, and documents chronicling various aspects of local history.
Meanwhile, the Water's Edge Museum focuses on the African American experiences in Oxford throughout the years, featuring artifacts that illustrate how the community lived. The Oxford Bellevue Ferry offers tourists a rare opportunity to ride on the country's oldest private ferry. Established in 1683, it takes you on relaxed cruises along the calmly flowing Tred Avon River.
Salisbury
Salisbury is a vibrant municipality on Maryland's Eastern Shore with something for everyone. It is the famous home of the Salisbury Zoological Park, a 12-acre wildlife sanctuary with a diverse variety of species. Families love coming here for unforgettable encounters with animals native to South America, North America, and Australia. Elsewhere, the Pemberton Historical Park offers a unique journey through time amidst beautiful natural surroundings. The property features Pemberton Hall, an 18th-century plantation home situated within a lush natural area, complete with woods, trails, ponds, and a creek.
Salisbury allows shopaholics, culinary buffs, and fun lovers to indulge in the pastime of choice at the Center at Salisbury. This expansive shopping mall is the largest on the Eastern Shore, housing a collection of branded retailers, entertainment venues, and dining options that span over 800,000 square feet.
Berlin
This Worcester County town impresses guests with its ever-infectious vibe, thanks to a vibrant downtown commercial district teeming with restaurants, galleries, museums, and breweries. The corridor is always bustling with activity, creating a perfect social environment for newcomers, especially at the Berlin Farmers Market. With dozens of growers, crafters, and vendors storming Main Street, the atmosphere is ideal for mingling and interacting.
Additionally, beer enthusiasts can sample Berlin's handcrafted brews at the Burley Oak Taproom & Brewing Company, a lively establishment that features live music. The Calvin B. Taylor House is a noteworthy landmark in downtown Berlin and a portal to the past. This Federal-style dwelling evokes small-town life in the Victorian period with its rare collection of rustic furniture, antiques, and memorabilia.
Chesapeake Beach
This picturesque waterfront village, situated on the shores of the Chesapeake Bay, offers travelers a wealth of water activities, delectable Chesapeake Bay cuisine, and outdoor exploration. The vast waters surrounding the town fuel aquatic activities, inviting fun-packed excursions into the bay, courtesy of Katherine Charter Fishing.
The Chesapeake Beach Railway Trail attracts outdoor enthusiasts seeking to explore the town's beauty along a 1.9-mile route, offering exquisite views of Fishing Creek and wildlife along the way. Lastly, nobody leaves Chesapeake Beach without tasting its famous seafood, particularly crab dishes. You can sample some of the best the town has to offer at Traders Seafood Steak & Ale, which serves favorites like crab cake sandwiches and drinks to go.
Cumberland
This picturesque town, nestled in the rugged mountain landscapes of Western Maryland, enchants vacationers with its rich natural surroundings and historic downtown area, lined with historic buildings. A walk through the district allows first-timers to get a glimpse of the early periods at the Gordon-Roberts House. This 1867 mansion welcomes guided tours, where you can explore Victorian furnishings and other relics that depict the lifestyle of its former owners.
Over 50,000 artifacts are exhibited at the Allegany Museum to chronicle Cumberland's rich and dynamic history, dating back to the original Native American residents. The best way to experience and appreciate the town's beauty is to hitch a ride on the Western Maryland Scenic Railroad. This classic ride on a steam engine traverses the forested wilderness of the Allegheny Mountains, offering a time-lapse of the spectacular countryside scenery.
Thurmont
Thurmont is a picturesque mountain town located near the Pennsylvania border, known for its numerous outdoor adventures, historic covered bridges, and tasty wines. It boasts a vast wilderness area, inviting outdoor immersion across the 5,200-acre expanse of Catoctin Mountain Park. Over 25 miles of trails snake throughout the park, opening doors for hikers, backpackers, campers, and fishermen to discover the reserve.
Families on vacation jump at the opportunity to interact with lovely wildlife species at the Catoctin Wildlife Preserve, which provides a home for hundreds of exotic animals from around the world. Driving down Thurmont's country roads will bring you to rustic covered bridges, such as the Roddy Road Covered Bridge from the mid-19th century. The well-preserved structure offers a glimpse into old-world craftsmanship. Lastly, remember to visit Catoctin Breeze Vineyard for a taste of local craft wines.
Ocean City
Ocean City is a popular summer destination on the scenic shores of the Atlantic Ocean, revered for its sandy beaches and lively atmosphere. The town hosts a series of festivals throughout the year, including the Oceans Calling Festival, which has earned it a reputation as a party central on the East Coast.
Outside the festival period, you will often find tourists and locals converging at the Ocean City Boardwalk. This busy corridor is lined with shops, restaurants, pubs, and ice cream bars, making it a major hub in the community. Those thinking of getting in the water can go to the nearby Ocean City Beach for a swim. Meanwhile, indoor enthusiasts can discover something interesting about the region's lifesaving heritage at the Ocean City Life-Saving Museum.
Whether planning to escape to the sandy beaches of Ocean City or explore the rugged trails of Thurmont, the cutest small towns in Maryland promise to leave you asking for more. Together, they capture the essence of the Old Line State, where coastal serenity, historic charm, and natural beauty come together in perfect harmony. Although each community offers a unique selection of local attractions, they are all a representation of Maryland’s most unforgettable experiences when you choose to hit the less-explored trails of the United States.
