Best Small Towns in Maryland
The best small towns in Maryland are St. Michaels for the Chesapeake Bay Maritime Museum, Chestertown for its 18th-century brick streets, Havre de Grace for its lighthouse and decoys, Berlin for a walkable Main Street near Assateague, and Cumberland for the end of the C&O Canal. Most sit on the Chesapeake, but the list also climbs into the western mountains. Here are 10 worth the trip, grouped by region.
- Best season: May through October; November for Easton’s Waterfowl Festival
- Regions: Upper Bay, Eastern Shore, Lower Shore, Southern Maryland, Western Maryland
- Closest big cities: Baltimore, Washington DC, Wilmington, Philadelphia, Pittsburgh
| Town | Region | Best for | Nearest airport |
|---|---|---|---|
| St. Michaels | Eastern Shore | maritime history, boat cruises, tasting rooms, weekend getaways, Frederick Douglass history | Baltimore/Washington (BWI), about 1 hr 30 min |
| Chestertown | Eastern Shore | colonial history, sailing, festivals, walkable downtowns, college-town culture | Baltimore/Washington (BWI), about 1 hr 30 min |
| Havre de Grace | Upper Bay | maritime history, waterfront walks, lighthouses, mountain biking, day trips from Baltimore | Baltimore/Washington (BWI), about 45 min |
| Berlin | Lower Shore | shopping, small museums, beaches, wild horses, day trips from Ocean City | Salisbury (SBY), about 35 min |
| Easton | Eastern Shore | art, live music, history, birding, fall festivals | Salisbury (SBY), about 1 hr |
| Solomons | Southern Maryland | boating, seafood, museums, fossil hunting, weekend getaways from Washington | Washington Reagan National (DCA), about 1 hr 30 min |
| Cumberland | Western Maryland | biking, trains, history, fall color, outdoor weekends | Hagerstown (HGR), about 1 hr 15 min |
| Chesapeake City | Upper Bay | ship watching, history, waterfront dining, cycling, B&B getaways | Philadelphia (PHL), about 1 hr |
| Oakland | Western Maryland | waterfalls, hiking, fall foliage, lake trips, skiing, railroad history | Morgantown, WV (MGW), about 1 hr 15 min |
| Crisfield | Lower Shore | island day trips, kayaking, crab feasts, Chesapeake history, decoy carving | Salisbury (SBY), about 45 min |
Eastern Shore
1. St. Michaels
St. Michaels is a Talbot County harbor town on the Miles River, once a shipbuilding and oyster center. The Chesapeake Bay Maritime Museum fills 18 waterfront acres, and the Cannonball House recalls the 1813 British attack. Walking tours trace Frederick Douglass's teenage years here.
Pop. 1,049 (2020 Census) Talbot County Founded 1804 (incorporated) Nearest airport: Baltimore/Washington (BWI), about 1 hr 30 min Known for: Chesapeake Bay Maritime Museum, the town that fooled the British, Frederick Douglass history, Miles River cruises
- Best for: maritime history, boat cruises, tasting rooms, weekend getaways, Frederick Douglass history
- Don't miss: Chesapeake Bay Maritime Museum; St. Michaels Museum at St. Mary's Square; Cruises on the Miles River
- Heads up: Route 33 is the only highway into town; arrive early on summer weekends.
2. Chestertown
Chestertown is the Kent County seat on the Chester River, a colonial Royal Port of Entry with more 18th-century homes than any Maryland town but Annapolis. You can sail on the schooner Sultana, walk a 29-stop historic district tour and time a visit for the Tea Party Festival or Downrigging.
Pop. 5,532 (2020 Census) Kent County Founded 1706 Nearest airport: Baltimore/Washington (BWI), about 1 hr 30 min Known for: 18th-century historic district, schooner Sultana, Washington College, Chestertown Tea Party Festival
- Best for: colonial history, sailing, festivals, walkable downtowns, college-town culture
- Don't miss: Schooner Sultana; Historic district walking tour; Chestertown Tea Party Festival
- Heads up: Sultana public sails are ticketed; book ahead.
3. Easton
Easton is the Talbot County seat and the Eastern Shore's arts hub, home to the free Academy Art Museum and the 1921 Avalon Theatre. The 1684 Third Haven Meeting House and the Hill, among the oldest free Black communities in the country, carry its history. Every November the Waterfowl Festival fills the streets.
Pop. 17,101 (2020 Census) Talbot County Founded 1710 (courthouse town); incorporated 1790 Nearest airport: Salisbury (SBY), about 1 hr Known for: Academy Art Museum, Avalon Theatre, Third Haven Meeting House, Waterfowl Festival
- Best for: art, live music, history, birding, fall festivals
- Don't miss: Academy Art Museum; Avalon Theatre; Third Haven Meeting House
- Heads up: Book lodging well ahead for the November Waterfowl Festival weekend.
Upper Bay
4. Havre de Grace
Havre de Grace sits at the mouth of the Susquehanna River, at the head of the Chesapeake Bay. Its free 1827 Concord Point Lighthouse, the Decoy Museum and the Maritime Museum line a waterfront promenade. Susquehanna State Park's trails and gristmill are just north of town.
Pop. 14,807 (2020 Census) Harford County Founded 1785 (incorporated) Nearest airport: Baltimore/Washington (BWI), about 45 min Known for: Concord Point Lighthouse, decoy carving, waterfront promenade, head of the Chesapeake Bay
- Best for: maritime history, waterfront walks, lighthouses, mountain biking, day trips from Baltimore
- Don't miss: Concord Point Lighthouse; Havre de Grace Decoy Museum; The Promenade and Tydings Park
- Heads up: Check the Lock House Museum's status before you go; the lighthouse is open weekends April through October only.
5. Chesapeake City
Chesapeake City is a Cecil County town of about 700 split in two by the Chesapeake & Delaware Canal. Ocean-going ships pass its 19th-century streets, the C&D Canal Museum keeps the old pump house, and a small ferry links the two sides in season. Waterfront restaurants, cruises and a canal trail round it out.
Pop. 736 (2020 Census) Cecil County Founded 1850 (incorporated) Nearest airport: Philadelphia (PHL), about 1 hr Known for: C&D Canal, ship watching, C&D Canal Museum, canal ferry
- Best for: ship watching, history, waterfront dining, cycling, B&B getaways
- Don't miss: C&D Canal Museum; Ship watching on the C&D Canal; Chesapeake City Ferry
- Heads up: The only car crossing is the high MD 213 bridge; the ferry links the two sides from mid-April to mid-October.
Lower Shore
6. Berlin
Berlin is a Worcester County town of about 5,000 whose brick Victorian Main Street starred in Runaway Bride and Tuck Everlasting. It has 60-plus shops and galleries, small museums, and a brewery. Assateague Island's wild horses are just down the road.
Pop. 5,026 (2020 Census) Worcester County Founded 1868 (incorporated) Nearest airport: Salisbury (SBY), about 35 min Known for: restored Victorian Main Street, Runaway Bride and Tuck Everlasting filming, gateway to Assateague Island
- Best for: shopping, small museums, beaches, wild horses, day trips from Ocean City
- Don't miss: Downtown Berlin and Main Street; Assateague Island National Seashore; Calvin B. Taylor House Museum
- Heads up: Summer weekends get busy with Ocean City traffic; use the public lot on Tripoli Street.
7. Crisfield
Crisfield is a waterfront city on Tangier Sound that once shipped seafood across the country. It's the jumping-off point for Smith Island and next door to Janes Island State Park's 30 miles of water trails. Every Labor Day weekend it hosts the National Hard Crab Derby.
Pop. 2,475 (2020 Census) Somerset County Founded 1663 (settled as Somers Cove); incorporated 1872 Nearest airport: Salisbury (SBY), about 45 min Known for: Seafood Capital of the World, Smith Island ferries, National Hard Crab Derby, Janes Island State Park, Ward Brothers decoys
- Best for: island day trips, kayaking, crab feasts, Chesapeake history, decoy carving
- Don't miss: Smith Island by boat; Janes Island State Park; Ward Brothers Workshop
- Heads up: Island cruises are seasonal and need reservations.
Southern Maryland
8. Solomons
Solomons sits at the southern tip of Calvert County, where the Patuxent River meets the Chesapeake Bay. The Calvert Marine Museum, with its climbable 1883 lighthouse, and the Smithsonian-affiliated Annmarie Sculpture Garden are the big draws. Calvert Cliffs' fossil beach is a short drive north.
Pop. 2,650 (2020 Census) Calvert County Nearest airport: Washington Reagan National (DCA), about 1 hr 30 min Known for: Calvert Marine Museum and Drum Point Lighthouse, Annmarie Sculpture Garden, boating and seafood
- Best for: boating, seafood, museums, fossil hunting, weekend getaways from Washington
- Don't miss: Calvert Marine Museum; Annmarie Sculpture Garden & Arts Center; Calvert Cliffs State Park
- Heads up: Summer weekends fill up with visitors from Washington and Baltimore; weekdays are quieter.
Western Maryland
9. Cumberland
Cumberland, the Allegany County seat, is where the 184.5-mile C&O Canal towpath meets the 150-mile Great Allegheny Passage. A restored steam train climbs 16 miles to Frostburg, and Washington Street's grand old houses recall its Queen City years. Rocky Gap State Park is just east of town.
Pop. 19,075 (2020 Census) Allegany County Founded 1787; incorporated 1815 Nearest airport: Hagerstown (HGR), about 1 hr 15 min Known for: end of the C&O Canal, start of the Great Allegheny Passage, Western Maryland Scenic Railroad
- Best for: biking, trains, history, fall color, outdoor weekends
- Don't miss: C&O Canal National Historical Park and Cumberland Visitor Center; Great Allegheny Passage; Western Maryland Scenic Railroad
- Heads up: Train seats sell out in fall; book ahead.
10. Oakland
Oakland is the Garrett County seat, a Victorian railroad town high in Maryland's mountains. It's the closest town to Swallow Falls and Herrington Manor state parks and sits at the south end of Deep Creek Lake. Its October Autumn Glory Festival is one of the state's best-known fall events.
Pop. 1,851 (2020 Census) Garrett County Founded 1851 (incorporated 1862) Nearest airport: Morgantown, WV (MGW), about 1 hr 15 min Known for: Swallow Falls and Muddy Creek Falls, 1884 B&O station, Autumn Glory Festival, Deep Creek Lake gateway, heavy snow
- Best for: waterfalls, hiking, fall foliage, lake trips, skiing, railroad history
- Don't miss: Swallow Falls State Park; Oakland B&O Museum and Train Station; Herrington Manor State Park
- Heads up: Swallow Falls requires day-use reservations on summer weekends and holidays.
- May–September: Boating season on the Chesapeake. Harbor cruises, crab houses and paddling trails are all running. Crisfield’s Hard Crab Derby closes the summer on Labor Day weekend. Book ahead for summer weekends in St. Michaels and Berlin.
- October–November: Cooler days suit the canal towpath and the western mountains. Easton’s Waterfowl Festival fills a weekend in November.
- Winter: Oakland is the snowiest place in Maryland, and Wisp Resort sits near Deep Creek Lake. Bay towns are quieter, and some tour boats stop for the season.
What is the prettiest small town in Maryland?
Chestertown is hard to beat, with brick mansions and townhouses from the 1700s along the Chester River. St. Michaels is the other strong pick.
What small towns in Maryland are best for a weekend?
Pair St. Michaels with Easton, since both are in Talbot County. From Baltimore, Havre de Grace is an easy trip up I-95.
What is the smallest town in Maryland worth visiting?
Chesapeake City had 736 people in 2020. It sits on both banks of the C&D Canal, with a canal museum, a 15-mile trail and boat cruises.
What are the best small towns in western Maryland?
Cumberland is where the C&O Canal towpath meets the Great Allegheny Passage to Pittsburgh. Oakland is the base for Deep Creek Lake.