Welcome to the delightful state of Maryland, a gem on the East Coast with stunning coastlines, rich colonial history, and charming small towns just waiting to be explored. If you’re looking to step away from the hustle and bustle of the major cities like Baltimore and discover the hidden treasures of Maryland, you’re in for a treat.
Join us as we journey through 15 of the best small towns to visit in Maryland. From arts festivals to outdoor adventures, and historic landmarks to delicious dining spots, these towns have something for everyone. Get ready to immerse yourself in the beauty and charm of these picturesque destinations that will make you feel like you’ve stepped back in time.
1. Thurmont, Maryland
Thurmont, located in Frederick County, is a small town nestled in the northern part of Maryland. Known as the “Gateway to the Mountains,” Thurmont boasts a historic downtown, beautiful nature trails, and a vibrant arts scene. If you’re an outdoors enthusiast or art lover, this town is a must-visit.
- Must-See Attractions:
- Catoctin Colorfest
- Cunningham Falls State Park
- Catoctin Mountain Park
- Loy’s Station Covered Bridge
- Catoctin Mountain Orchard
- Springfield Manor Winery and Distillery
2. Berlin, Maryland
Don’t confuse Berlin, Maryland with the European capital – this charming town in Worcester County has its own unique charm and history. Known for its fishing and hunting grounds, Berlin has revitalized its downtown area and is now a popular destination for visitors looking to experience small-town charm on the East Coast.
- Must-Do Activities:
- Assateague State Park
- Dr. Shred’s Surf Adventures
- Burley Oak Brewing Company
- Maryland Wine Bar
- The Blacksmith
- Bakes Dessert Cafe
3. Hampstead, Maryland
Located in Carroll County, Hampstead was once an agricultural hub and has now transformed into a modern town with a rich history. Whether you’re a nature lover or a food enthusiast, you’ll find plenty to explore in this quaint Maryland town.
- Top Highlights:
- Happy on Hooves
- Prettyboy Reservoir Park
- Leister Park
- A Town Bar and Grille
- Snickerdoodles Bakery and Coffee House
- Hilltop Hideaway Bed and Breakfast
4. Crisfield, Maryland
Crisfield, a town in Somerset County, is known as the “Seafood Capital of the World” and offers a glimpse into Maryland’s fishing heritage. With festivals, seafood bakes, and scenic tours, Crisfield is a seafood lover’s paradise waiting to be explored.
- Don’t Miss Out On:
- National Hard Crab Derby
- J. Millard Tawes Crab and Clam Bake
- Scorchy Tawes Pro-Am Fishing Tournament
- Janes Island State Park
5. Eastport, Maryland
For a laid-back coastal experience just across the bridge from Annapolis, Eastport is the perfect destination. With waterfront views, watersports activities, and charming dining spots, Eastport offers the best of both worlds – relaxation and adventure.
- Must-Visit Spots:
- Carrol’s Creek Cafe
- Third and Severn
- Maritime Museum
- Davis’ Pub
- Ocean City Beach and Boardwalk
- Odyssea Watersports
6. Ocean City, Maryland
Ocean City, a resort destination in Worcester County, is a popular coastal getaway for tourists from the Mid-Atlantic region. With luxury resorts, waterfront dining, and exciting water activities, Ocean City is the perfect destination for a summer escape.
- Top Things To Do:
- Princess Royale Resort
- Hobbit Restaurant
- Harborside Bar
- Ocean City Beach and Boardwalk
- Odyssea Watersports
7. Havre de Grace, Maryland
Situated at the confluence of the Susquehanna River and the Chesapeake Bay, Havre de Grace is a picturesque town with a French connection. With historic landmarks, scenic promenades, and vineyards, Havre de Grace offers a peaceful retreat for visitors.
- Explore These Gems:
- Spencer-Silver Mansion
- Havre de Grace Promenade
- Concord Point Lighthouse
- Susquehanna State Park
- Mount Felix Vineyard & Winery
8. Monkton, Maryland
Escape to the countryside in Monkton, a charming town in Baltimore County known for its horse farms and historic homes. Whether you’re a nature lover or a foodie, Monkton has a variety of activities to suit every traveler.
- Discover Monkton:
- “My Lady’s Manor”
- Ladew Topiary Gardens
- Millstone Cellars
- Gunpowder Bison & Trading Co
9. Oakland, Maryland
Located in Garrett County, Oakland is a former railroad town with a rich history and natural beauty. From historic train stations to sprawling parks, Oakland offers a peaceful getaway for nature lovers and history buffs.
- Must-See Sites:
- Swallow Falls State Park
- Circle R Ranch
- Lodestone Golf Club
- Will O’ the Wisp hotel
10. St Mary’s City, Maryland
Step back in time to the colonial era in St Mary’s City, the site of Maryland’s first colonial settlement. With living history museums, colonial farms, and historic ships, St Mary’s City is a paradise for history enthusiasts.
- Uncover History at:
- Reconstructed Colonial Settlement
- The Dove Sailing Ship
- Living History Museums
11. New Market, Maryland
Known as the “Antiques Capital of Maryland,” New Market is a charming town in Frederick County with a rich history. Explore the downtown area, visit antique shops, and enjoy the town’s annual festivals to experience the best of New Market.
- Highlights of New Market:
- Antique Shops
- Christmas in New Market
- A Day in New Market
- Vintage
- Strawberry Inn B&B
12. Vienna, Maryland
Surrounded by lush greenery and located on the Nanticoke River, Vienna is a hidden gem in Dorchester County. From vineyards to waterfront views, Vienna offers a tranquil escape for visitors seeking peace and serenity.
- Relax and Unwind at:
- Layton’s Chance Vineyard and Winery
- Tavern House
- River Pavilion
13. Emmitsburg, Maryland
Emmitsburg, located in Frederick County, is a pilgrimage site with a rich Catholic heritage. From historic shrines to charming inns, Emmitsburg offers a peaceful retreat for visitors seeking spiritual reflection and relaxation.
- Discover Emmitsburg:
- National Shrine Grotto of Our Lady of Lourdes
- Basilica and National Shrine of St. Elizabeth Ann Seton
- Mason Dixon Welcome Center
- Mount St. Mary’s University
- Emmitsburg Antique Mall
14. Leonardtown, Maryland
As the county seat of St. Mary’s County, Leonardtown is a seafood lover’s paradise with a vibrant downtown area and waterfront attractions. From shopping to watersports, Leonardtown offers a variety of activities for visitors of all interests.
- Experience Leonardtown:
- Leonardtown Wharf
- Tudor Hall
- St. Andrew’s Church
- Fitzies Marina Restaurant and Pub
- Executive Inn
15. St. Michaels, Maryland
Named after an Episcopal Parish established in the 17th century, St. Michaels is a historic town in Talbot County with a rich maritime history. From historic landmarks to fresh seafood, St. Michaels offers a charming coastal experience for visitors.
- Must-Visit Attractions:
- Cannonball House
- Historic District
- Chesapeake Bay Maritime Museum
- St. Michaels Crab & Steak House
Whether you’re a history buff, a nature enthusiast, or a foodie, these 15 small towns in Maryland have something for everyone. From scenic views to historic sites, delicious dining spots to outdoor adventures, these towns offer a perfect blend of charm, culture, and relaxation. So pack your bags, hit the road, and explore the hidden gems of Maryland’s small towns – you won’t be disappointed!