Here are 15 charming small towns in Maryland that most travelers tend to miss but are definitely worth visiting for their quaint atmosphere, rich history, and scenic beauty:
1. Emmitsburg
Nestled in Frederick County with rolling hills, historic sites like the National Shrine of St. Elizabeth Ann Seton, and outdoor trails for hiking and biking.
2. Thurmont
A haven for art and nature lovers with access to Catoctin Mountain Park, Cunningham Falls, and local history exhibits.
3. Monkton
Known for natural beauty and historic sites like Ladew Topiary Gardens, featuring amazing hiking and historic architecture.
4. Hampstead
Rich in small-town charm, scenic parks, festivals, and historic buildings like the Hampstead Train Station Museum.
5. Leonardtown
Maryland’s oldest incorporated town with colonial architecture, waterfront views, and arts and culture events.
6. Berlin
Historic town near Assateague Island famous for quirky festivals like the Bathtub Races and numerous preserved 18th- and 19th-century buildings.
7. Bel Air
A town combining historic charm with vibrant local shops, eateries, and cultural events close to Baltimore.
8. St. Michaels
Charming waterfront town known for maritime history, boutique shopping, and the Chesapeake Bay Maritime Museum.
9. Chesapeake City
A scenic canal town with historic homes, local shops, and delicious seafood diners.
10. Oakland
A gateway to western Maryland’s outdoor adventures with a quaint downtown and Victorian architecture.
11. Vienna
A small town with friendly community vibes and historical local sites off the beaten path.
12. Havre de Grace
Not far from the Susquehanna River, known for its picturesque waterfront, museums, and lively local arts scene.
13. Easton
Offers historic streets, art galleries, and a lovely farmers market in the heart of Maryland’s Eastern Shore.
14. Cumberland
Undergoing downtown revitalization, this historic town boasts trails, local dining, and river views for a relaxed visit.
15. Boonsboro
A small town with scenic beauty, historic landmarks, and a peaceful atmosphere ideal for quiet retreats.
These small towns in Maryland combine rich history, natural beauty, and welcoming communities quietly off the typical tourist track, perfect for travelers seeking authentic, peaceful Americana experiences.
Sources
(https://traveltriangle.com/blog/small-towns-in-maryland/)
(https://www.worldatlas.com/cities/most-underrated-towns-in-maryland-2025.html)
(https://www.worldatlas.com/cities/8-cutest-small-towns-in-maryland-for-2025.html)
(https://www.hotels.com/go/usa/must-visit-small-towns-maryland)
(https://itravelforthestars.com/towns-in-maryland/)
