8 Stunning Small Towns In Maryland
Small-town life in Maryland is defined by history, as one of the founding 13 states, and by the importance of maritime life with Chesapeake Bay as the heart of the state. As the largest estuary in the United States, the bay is a crucial economic, cultural, and historic center of Maryland. In Havre de Grace, the Susquehanna River meets the Chesapeake Bay beside the scenic Havre de Grace Promenade and the 1827 Concord Point Lighthouse, giving the town one of the state’s most memorable waterfront settings. St. Michaels is equally striking for its red-brick historic district, working shipyard atmosphere, and the Chesapeake Bay Maritime Museum’s 1879 Hooper Strait Lighthouse. Below are the 8 most beautiful towns in Maryland.
Havre de Grace
This beautiful town is located at the confluence of the Susquehanna River and Chesapeake Bay. The waterfront is a key part of the town’s history, with the bayside Havre de Grace Promenade as an iconic focal point. This 0.75-mile boardwalk runs along the bay and offers perfect opportunities for strolling and birdwatching. With its historic and downtown district, Havre de Grace is also notable for almost becoming the US capital in 1789, losing by only one vote.
One of Maryland’s oldest lighthouses, located at the northernmost point of the Chesapeake Bay, the Concord Point Lighthouse was built in 1827 and is an iconic symbol of the town. The downtown district is centered around Washington Street, and its antique stores are a huge draw, including the Seneca Cannery Antique Mall, which is the largest in the county. Just outside of town is the Susquehanna State Park, featuring trails for hiking and mountain biking, plus lots of opportunities for fishing. Back in town, the Maritime Museum & Lock House Museum offers insight into the area’s canal and maritime histories.
Berlin
Getting away from beach resorts is a big draw for visitors to Berlin. Just 10 miles from Ocean City, Berlin is a quieter and slower-paced town with a lively Main Street and well-preserved architecture. Berlin has several historic districts and over 47 structures listed on the National Register of Historic Places. Main Street is a thriving commercial district with locally-owned shops, antique stores, and restaurants.
Right downtown, you can find the Calvin B. Taylor House Museum, inside a restored 1832 house and with a focus on local history. The Atlantic Hotel is a central part of downtown, built in 1895 and known for its Victorian architecture and its inviting porch with rocking chairs. Not far from downtown is Assateague State Park, Maryland’s only oceanfront park. The park is famous for its wild horses and has a beautiful beach.
The town is big on local goods and services, with "Made in Berlin" logos identifying local products in the independent shops along Main Street and throughout the historical districts. There's also the Berlin Farmers Market, which takes place every Sunday from May through September and features over 50 local vendors.
Chestertown
This historic college town is known for its Main Street and its beautifully preserved 18th-century homes. Chestertown’s scenic waterfront is located on the Chester River. This port city was once one of the major ports in the state, and it is home to Washington College, the 10th-oldest college in the United States. Chestertown is celebrated for its maritime heritage and a thriving art scene, as well as its well-preserved historical buildings. The Historic District has the second-largest number of 18th-century homes in Maryland, after Annapolis.
The Historical Society of Kent County is an important center for education on the town’s role in the Underground Railroad and in African American history. An important part of Chestertown's history and a major festival today, the Chestertown Tea Party Festival is held every year on the Memorial Day weekend. It celebrates Chestertown’s own historical tea party, an act of defiance in 1774 against the British authorities. The festival features a parade, colonial crafts, and a re-enactment of the tea party. For more contemporary crafts and foods, the Chestertown Farmers & Artisans Market is a year-round market featuring local produce, goods, and crafts.
St. Michaels
A historic waterfront town on the Eastern Shore, St. Michaels is known as the heart of Chesapeake Bay. The town is beautiful in its maritime charm and ambience, and is an important tourism location for boating, colonial history, and seafood. In particular, St. Michaels is famed for its oystering and crabbing heritage. The historic district features red brick sidewalks and Victorian structures now housing locally-owned businesses and antique shops.
The Chesapeake Bay Maritime Museum covers 18 acres and features the 1879 Hooper Strait Lighthouse. There is a working shipyard plus interactive exhibits on the area’s history in crabbing and oystering. In the Historic District, St. Michaels Museum at St. Mary's Square offers walking tours highlighting the history of the town, its role in the War of 1812, and the life of Frederick Douglass.
The Historic District and the waterfront are rich in opportunities to take in the famed local seafood, fresh from the bay. At the Chesapeake Bay Maritime Museum, every fall, the St. Michaels OysterFest celebrates the oystering heritage, taking place in late October or early November.
Ellicott City
By far the most populous town on this list, Ellicott City, with its dramatic valley setting, is a well-preserved 18th-century mill town. Situated in the scenic valleys of the Tiber and Patapsco rivers, Ellicott City is a drivable distance from both Baltimore and Washington, DC. The Ellicott City Historic District is a nationally recognized historic district featuring more than 200 buildings dating back to the 18th and 19th centuries. There are over 70 independent shops, galleries, and restaurants within the district.
The B&O Railroad Station Museum is contained within the oldest surviving passenger train station in the United States. The ruins of the 19th-century Patapsco Female Institute are now used for theatrical performances, while local lore tells of hauntings at the former girls’ finishing school. For a glimpse of settler life, the Thomas Isaac Log Cabin is one of the town's original homes, dating back to the 18th century. A more contemporary destination, Koreatown offers authentic Korean food, bakeries, and markets.
Chesapeake City
This picturesque town is located on the canal connecting Chesapeake Bay with the Delaware River. The town is actually divided by the canal into two distinct districts: primarily residential North and South, featuring the Historic District and most of the shops and restaurants. Chesapeake City features well-preserved Victorian architecture and a maritime heritage centered around the canal.
A small town of around 752 residents, Chesapeake City nevertheless features amenities and sights worth visiting. Waterfront dining along the canal, mostly on the South side, offers views of the large ocean-going vessels passing through. Throughout the warmer months, Sip & Stroll is a chance to tour the historical district while sampling wine, beer, and spirits. Chesapeake City Ferry is a seasonal transport option connecting North and South Chesapeake City. The C&D Canal Museum is located in the historic lock pump house and details the history of the canal. The museum features an original waterwheel. The Ben Cardin C&D Canal Trail is a multi-use trail connecting with Delaware’s Mike Castle Trail.
Boonsboro
This town, founded in 1792 by cousins of Daniel Boone, is located near the Appalachian Trail, at the foot of South Mountain. The official spelling of the town name is Boonsboro, although it was historically spelled Boonesborough; variations of the latter spelling are sometimes used for historical purposes. The town serves as an important gateway to colonial and Civil War sites, such as the National Road and Antietam National Battlefield. In addition to its history, the town is now a literary destination, thanks to the revitalization effort of author Nora Roberts.
Local destinations include Washington Monument State Park, which is home to the first monument dedicated to George Washington. The site offers beautiful panoramic views of the landscape. Boonsboro is Maryland’s first designated Appalachian Trail Community, and the town is a popular stop for hikers. The Crystal Grottoes Caverns are underground caverns open to the public and featuring unique geological formations.
In town, the Boonsborough Museum of History has an extensive Civil War collection. A major annual town event, Boonesborough Days, is held on the Labor Day weekend, focusing on 100% handmade crafts, with over 150 exhibitors, and Civil War displays.
Cumberland
Located in the Allegheny Mountains, Cumberland is considered the Gateway to the West. It once served as a key 19th-century transportation hub where the National Road, the B&O Railroad, and the Chesapeake & Ohio (C&O) Canal all met. One key attraction linking the town to its transportation past is the Western Maryland Scenic Railroad. This heritage railroad features vintage steam and diesel train trips through the Allegheny Mountains.
Maryland’s first certified Heritage Area, Canal Place was the western terminus of the C&O Canal and features a full-scale canal boat replica, as well as a 1750s log cabin in nearby Riverside Park that once served as George Washington’s headquarters. The historic downtown district is dotted with independent stops and restaurants.
Historic sites include the Emmanuel Episcopal Church, located near the site of Fort Cumberland, which contains historic tunnels that local sources suggest may have been used in Underground Railroad activities. The Great Allegheny Passage is a 150-mile rail-trail for hiking and cycling, connecting Pittsburgh, Pennsylvania, to Cumberland. It then connects with the C&O Canal Towpath and continues 184.5 miles to Washington.
Beautiful Heart Of Maryland Life
Maryland’s small towns capture the state’s history, culture, and maritime heritage in charming settings. From scenic waterfronts and historic districts to bustling streets lined with local shops and cafes, these communities offer a glimpse into colonial life, Victorian architecture, and enduring traditions. Whether exploring museums, strolling along boardwalks, or simply taking in the small-town atmosphere, visitors can experience the character and timeless appeal of this great state.
