These 10 Towns In Maryland Were Ranked Among US Favorites In 2025
Maryland is filled with small towns that capture a uniquely American blend of history, charm, and community. In 2025, a notable 10 of these towns have risen to the top of "favorite towns" lists across the US. From harbor front strolls to mountain trails, these destinations showcase historic architecture, local festivals, arts and crafts, and water activities. Here, we will explore each of these 10 towns, examining what makes them special, what you must see when you visit, and why they resonate with visitors and residents alike in 2025.
Annapolis
Although Annapolis, in Anne Arundel County, is the capital of Maryland, it still qualifies as a small town, with a population of 40,800. Sitting at the mouth of the Severn River on the Chesapeake Bay, Annapolis, with over seven square miles of area, offers much to see and do. This may be why CNN Travel named Annapolis one of "America's Best Towns to Visit" in 2025.
Annapolis was the capital of the US from 1783 to 1784, and its rich history is reflected in its streets today. The Maryland State House, the oldest state capitol still used, is one historic place in town that you can tour. If you prefer the arts, check out Maryland Hall, dedicated to Art for All since 1979. Take a trolley tour with Towne Transport to see all of the historic area in just one hour. Along the town's waterfront, visit the Annapolis Maritime Museum and Park, located in the former McNasby Oyster Company building.
Berlin
The historic town of Berlin in Worcester County was called the "Coolest Small Town in America" in 2022 by Baltimore Magazine. Its small-town charm has drawn filmmakers to use the town as a backdrop for the 1998 film "Runaway Bride" and 2001's "Tuck, Everlasting."
To learn more about Berlin's history, check out the Calvin B. Taylor House, a historic house museum on Main Street. The Mermaid Museum is a unique collection of mermaid memorabilia and artifacts from around the world. The unspoiled natural beauty of Assateague Island is just 20 minutes away and is known for its population of wild horses, which roam the island. If you crave the hustle and bustle of the beach, Ocean City's Boardwalk is also a 20-minute drive from Berlin.
Chestertown
Chestertown, located in Kent County, is home to approximately 5,500 people and was founded in the 1700s along the banks of the Chester River on Maryland's Eastern Shore. The Port of Chestertown Marina received the 2024 Maryland Clean Marina award in recognition of its efforts to prevent pollution. In addition to 15 transient slips and a public boat ramp, the marina includes office buildings and is just one block from Chestertown's downtown area.
Washington College in Chestertown, the first college chartered in the sovereign US, is also worth visiting. Check out Chestertown's Farmers' & Artisans' Market each on High and Cross Street every Saturday year-round for farm-fresh produce and local arts and crafts. To learn more about the town's history, visit the Historical Society of Kent County, which contains documents and artifacts dating to the early 1700s.
Cumberland
The Allegany County town of Cumberland, also known as the "Queen City" due to its former status as the second-largest town in Maryland, is home to approximately 19,000 people today. USA Today named Allegany County one of its 10 "Best Places to Visit for Fall" in 2025. Situated in the Appalachian Mountains, Cumberland is renowned as a hub of history, art, and culture.
Take a ride on the Western Maryland Scenic Railroad to see the mountains and beauty from Cumberland to Frostburg. For a truly unique experience, check out the Chesapeake & Ohio Canal-Paw Paw Tunnel, a 3,118-foot-long tunnel cut through a hill to shorten the canal by six miles. This can be explored on foot or by bike. The arts are evident throughout Cumberland, with notable examples including the Ferleman Gallery on Centre Street, showcasing world-class fine art, and the Embassy Theatre on Baltimore Street, which offers live performances.
Easton
The Talbot County town of Easton sits along the Chesapeake Bay near the head of the Tred Avon River along Maryland's Eastern Shore. This town of about 17,000 was a runner-up in USA Today's poll for "Best Small Town Cultural Scene" in 2025. The town's rich history, combined with its arts and culture, makes visiting Easton a can't-miss experience.
Take the Historic Easton Walking Tour to discover more about the town's rich history. The Talbot Historical Society Museum & Garden can also enlighten you on the history of the entire area. If you visit Easton on the first Friday of the month, the First Friday Gallery Walk showcases the art galleries, shops, and restaurants in the downtown area. The Waterfowl Festival, celebrating its 50th anniversary, takes place on the second weekend of November and attracts nearly 20,000 visitors from around the country to celebrate wildlife art and the work of artisans.
Havre de Grace
Harford County's Havre de Grace, along the Susquehanna River, is a beautiful town that lives up to its name, meaning "port of grace." Approximately 14,800 people reside in Havre de Grace, which received the Sustainable Maryland Certified Award in 2019 from the University of Maryland's Environmental Finance Center, recognizing the town as one of Maryland's most sustainable communities.
The Promenade Boardwalk runs for almost a mile along the Susquehanna River and makes for a leisurely nature walk. The Concord Point Lighthouse, Maryland's second-oldest lighthouse, is a renowned landmark in Havre de Grace that is open for visitation on weekends from April to October. Susquehanna State Park offers over 15 miles of marked trails for hiking and biking. The Havre de Grace Farmers Market, located on Pennington Avenue, operates on Saturdays from May through December, featuring local produce and crafts from area artisans.
Leonardtown
The county seat of St. Mary's County in southern Maryland, Leonardtown, home to about 4,500 people, sits along Breton Bay and was once a busy port and steamboat landing site. The Maryland Municipal League recognized Leonardtown as a Banner City in 2025 for its demonstrated commitment to the municipality. There is much to see and do in this waterfront town.
Visit the Port of Leonardtown Park, where you can see Mcintosh Run Trail, a six-mile-long water trail that runs from Leonardtown Wharf Park to Abell's Wharf. The Leonardtown Butterfly Trail highlights historic landmarks and engaging activities in town. Check out the Old Jail Museum for a fun, historic experience. Wine lovers can visit the Port of Leonardtown Winery to sample its award-winning wines.
Oakland
In far western Maryland's Garrett County, the town of Oakland, with a population of 1,850, is surrounded by the Appalachian Mountains. It's easy to see why this small, charming town draws so many visitors, not just in autumn but year-round. It is just 15 minutes from Maryland's famous Deep Creek Lake, a man-made reservoir popular in all four seasons.
The Garrett County Historical Society Museum in Oakland tells the story of the area's founding and history. If you are interested in railroad history, the Oakland B&O Railroad Museum is a must-see. Outdoor lovers should check out Broadford Lake Park in town, complete with picnic areas, a beach with a swimming area, playgrounds, and sports courts.
St. Michaels
Talbot County's town of St. Michaels may be home to just 1,050 people, but it draws thousands of visitors year-round. It was voted the "Best Coastal Small Town" by Southern Living in 2024. St. Michaels sits on the Miles River, a tributary of the Chesapeake Bay, and the St. Michaels Harbor on the waterfront is a popular destination for boaters.
The Chesapeake Bay Maritime Museum features exhibits on navigation, boatbuilding, and oystering. If you prefer being outdoors, take the St. Michaels Nature Trail, a 1.3-mile-long rail trail from Railroad Avenue to Heathington Farm Road. Wine lovers should check out the St. Michaels Winery on Talbot Street, featuring 18 distinct wines.
Sykesville
In Howard and Carroll Counties, Sykesville is conveniently situated 25 miles west of Baltimore and 40 miles north of Washington, DC. It was a "Great American Main Street" semi-finalist in the 2025 National Main Street America program. This town on the Patapsco River is filled with activities for all ages.
The Gate House Museum, situated in Millard Cooper Park, showcases the town's artifacts and collections. A visit to the Sykesville Historic Colored Schoolhouse is also enlightening and educational. The Little Sykes Railway Park, open on Sundays in summertime, gives free rides on a 1949 12-gauge miniature train through two acres of parkland. The Sykesville Farmers Market is open on Sundays from May through October, featuring local produce, baked goods, and specialty items.
Favorites of the Free State
These 10 Maryland towns each offer visitors a multitude of special things to see, do, and experience. Maryland's rich history shines through in each of these towns. From the waterfront hubs of St. Michaels, Havre de Grace, and Easton, to the mountain splendor of Oakland and Cumberland, these destinations offer unique and enjoyable experiences for visitors of all ages. It is easy to see why travelers should put these 10 Maryland towns on their must-visit list for 2025.
