Small Towns Near Baltimore
The best small towns near Baltimore are St. Michaels, Chestertown and Havre de Grace. St. Michaels has the Chesapeake Bay Maritime Museum, and Chestertown was a colonial port founded in 1706. Havre de Grace has a free lighthouse and a decoy museum at the top of the Bay.
The eleven towns below run nearest first, from Stevensville on Kent Island, about 25 miles out, to Crisfield and Berlin, about 100 miles away. Most sit on the Chesapeake Bay or the Eastern Shore, so this list leans toward water, boats and colonial history.
| Town | Distance | Best for |
|---|---|---|
| Stevensville, Maryland | About 25 miles | Bay views, a short first stop |
| Mount Airy, Maryland | About 30 miles | railroad history, Main Street |
| Chestertown, Maryland | About 30 miles | colonial history, a college town |
| Havre de Grace, Maryland | About 35 miles | lighthouse, decoys, waterfront walk |
| St. Michaels, Maryland | About 40 miles | maritime history, harbor, a weekend |
| Chesapeake City, Maryland | About 45 miles | canal views, a small historic district |
| Easton, Maryland | About 45 miles | arts, a festival weekend |
| Solomons, Maryland | About 65 miles | marine museum, fossils, the water |
| St. Mary’s City, Maryland | About 75 miles | colonial history, living history |
| Crisfield, Maryland | About 100 miles | crabs, kayaking, island ferries |
| Berlin, Maryland | About 100 miles | Main Street, beaches, wild horses |
Distances are straight-line miles from downtown Baltimore, Maryland, as the crow flies.
Stevensville, Maryland
About 25 miles as the crow flies · Best for: Bay views, a short first stop
Stevensville started in 1850 as a steamboat landing on Kent Island. It sits at the eastern end of the Chesapeake Bay Bridge, so it’s the first town you reach on the Eastern Shore. Its historic district holds roughly 100 old buildings.
Don’t miss: the Chesapeake Heritage & Visitor Center at Kent Narrows, with exhibits and observation towers, and the six-mile Cross Island Trail nearby
★ Good to know The visitor center is open May through November.
Mount Airy, Maryland
About 30 miles as the crow flies · Best for: railroad history, Main Street
Mount Airy straddles the line between Frederick and Carroll counties and grew up along the B&O Railroad. The name reportedly came from a B&O worker complaining about his cold ears. It’s a town of about 9,700.
Don’t miss: the Caboose Visitor Center downtown and the Twin Arch Bridge, a railroad bridge from 1901
★ Good to know The town’s things-to-do page also points to a rail trail and a drugstore museum.
Chestertown, Maryland
About 30 miles as the crow flies · Best for: colonial history, a college town
Chestertown was founded in 1706 and became one of Maryland’s Royal Ports of Entry. Washington College was founded here in 1782. The town of about 5,500 sits on the Chester River.
Don’t miss: the Sultana, a reconstruction of a British schooner launched in 2001, and the Washington College campus
★ Good to know Sultana Downrigging, a tall-ship festival, runs October 30 to November 1 in 2026.
Havre de Grace, Maryland
About 35 miles as the crow flies · Best for: lighthouse, decoys, waterfront walk
Havre de Grace sits where the Susquehanna River meets the Chesapeake Bay. It reportedly missed being named the U.S. capital by one vote in 1789. It’s a city of about 14,800 with a waterfront promenade rebuilt in 2004.
Don’t miss: the Havre de Grace Decoy Museum, founded in 1986, and Concord Point Lighthouse, with free admission to the tower and keeper’s house
★ Good to know Concord Point Lighthouse is open April through October and closed November through March except for special events.
St. Michaels, Maryland
About 40 miles as the crow flies · Best for: maritime history, harbor, a weekend
St. Michaels is known as “the town that fooled the British” after an 1813 raid. Shipyards here built Baltimore Clippers in the early 1800s. Frederick Douglass lived here as an enslaved young man in the 1830s.
Don’t miss: the Chesapeake Bay Maritime Museum on the harbor, with the Hooper Strait Lighthouse, a working shipyard and a floating fleet
★ Good to know The maritime museum is open daily April through November; check winter hours before you go.
Chesapeake City, Maryland
About 45 miles as the crow flies · Best for: canal views, a small historic district
Chesapeake City is a town of about 740 on the Chesapeake and Delaware Canal, which opened in 1829. The town took its current name in 1839. A tall bridge built in 1949 now carries traffic over it.
Don’t miss: the C&D Canal Museum on Bethel Road, run by the U.S. Army Corps of Engineers, and the shops along Bohemia Avenue in the South Chesapeake City Historic District
★ Good to know The canal museum is self-guided and adds weekend hours between Memorial Day and Labor Day.
Easton, Maryland
About 45 miles as the crow flies · Best for: arts, a festival weekend
Easton grew up around a Talbot County courthouse authorized in 1710. Its Hill neighborhood is believed to be the oldest free African American community in the country. It’s a town of about 17,100.
Don’t miss: the Avalon Theatre, which books music and theater through the year, and the Third Haven Meeting House
★ Good to know The 55th Waterfowl Festival runs November 13 to 15, 2026, and it fills the town.
Solomons, Maryland
About 65 miles as the crow flies · Best for: marine museum, fossils, the water
Solomons sits at the southern tip of Calvert County, where the Patuxent River meets the Bay. More than 60,000 troops trained here for amphibious landings in World War II. It’s a village of about 2,650.
Don’t miss: the Calvert Marine Museum, with the Drum Point Lighthouse, fossils from Calvert Cliffs and a river otter habitat
★ Good to know The museum runs cruises on the Wm. B. Tennison, a historic bugeye; check its site for the schedule.
St. Mary’s City, Maryland
About 75 miles as the crow flies · Best for: colonial history, living history
Maryland was founded here on March 27, 1634, and this was the colony’s capital until 1694. Today the town is mostly a state-run outdoor museum and St. Mary’s College.
Don’t miss: Historic St. Mary’s City, with the reconstructed State House, a Woodland Indian Hamlet and the Maryland Dove, a working replica of a settler ship
★ Good to know The museum is open Tuesday through Saturday into November, so plan a fall visit early.
Crisfield, Maryland
About 100 miles as the crow flies · Best for: crabs, kayaking, island ferries
Crisfield called itself the Seafood Capital of the World after the railroad arrived in 1866. It’s a city of about 2,500 at Maryland’s southern edge. Passenger ferries leave the city dock for Smith Island and Tangier Island.
Don’t miss: Janes Island State Park, with more than 30 miles of marked water trails through 2,900 acres of salt marsh
★ Good to know The park’s five miles of beach are reachable only by boat.
Berlin, Maryland
About 100 miles as the crow flies · Best for: Main Street, beaches, wild horses
Berlin has 47 structures on the National Register of Historic Places. Its Main Street stood in for fictional towns in Runaway Bride (1999) and Tuck Everlasting (2002). It’s a town of about 5,000 in Worcester County.
Don’t miss: Assateague Island National Seashore, whose Maryland district is open year-round and known for its wild horses
★ Good to know Watch the horses from a distance; the park asks visitors not to approach them.
What’s the closest small town to Baltimore worth a day trip?
Stevensville, on Kent Island, is about 25 miles away as the crow flies. It’s at the east end of the Bay Bridge, and the Cross Island Trail starts nearby.
What’s the best small-town weekend trip from Baltimore?
St. Michaels is the easiest weekend, with the Chesapeake Bay Maritime Museum on the harbor. Easton is close by, so you can pair the two.
Which small towns near Baltimore have lighthouses?
Havre de Grace has Concord Point Lighthouse, open April through October. St. Michaels has the Hooper Strait Lighthouse at its maritime museum, and Solomons has the Drum Point Lighthouse.
Where can you see wild horses near Baltimore?
Assateague Island National Seashore, next to Berlin, has wild horses and its Maryland district is open year-round. Berlin is about 100 miles from Baltimore as the crow flies.