Maryland is home to a variety of scenic small towns, each offering its own unique charm, history, and character. Whether nestled in the mountains or perched by a river, these towns are often overlooked by travelers heading to the more famous cities. Here are 10 of Maryland’s most charming—and sometimes underrated—small towns that should be on your bucket list.
1. Thurmont
Located in the heart of the Catoctin Mountains, Thurmont is a paradise for outdoor enthusiasts. The town offers beautiful scenic views and plenty of hiking opportunities at Catoctin Mountain Park. For a fun autumn experience, don’t miss the Catoctin Colorfest, a lively local festival celebrating the season’s colors.
2. Hancock
Situated along the Potomac River in Western Maryland, Hancock is a quiet retreat for nature lovers. The town is well-known for its access to the Western Maryland Rail Trail, which is perfect for biking and hiking. The charming downtown, with its specialty shops and the Blue Goose Family Market, offers a unique old-town experience.
3. Emmitsburg
Emmitsburg, surrounded by rolling hills and picturesque countryside, is a town steeped in history. It offers visitors a chance to explore historic buildings, dine at cozy restaurants, and visit the National Shrine of St. Elizabeth Ann Seton. If you’re into outdoor activities, the Emmitsburg Trail is perfect for hiking and biking.
4. Bel Air
Bel Air, located in Harford County, offers a vibrant small-town experience with a lively downtown area full of independent boutiques and restaurants. Visitors can also enjoy the town’s art scene, farmers’ markets, and nearby parks, making it a great place for a laid-back afternoon.
5. Havre de Grace
Where the Susquehanna River meets the Chesapeake Bay, Havre de Grace is a historic town with plenty of charm. The town features a scenic promenade, the iconic Concord Point Lighthouse, and delicious Chesapeake seafood served at its waterfront eateries. History lovers and foodies will appreciate the local museums and art galleries.
6. Oxford
Founded in 1683, Oxford is one of Maryland’s oldest towns, known for its tranquil pace and beautiful riverfront. The Oxford-Bellevue Ferry, which has been in operation since the 19th century, is a fun way to experience the town. Oxford also offers a fantastic seafood dining scene and a relaxing atmosphere perfect for a peaceful getaway.
7. St. Michaels
St. Michaels is a town rich in maritime history, where cobblestone streets and historic homes create a picturesque atmosphere. A visit to the Chesapeake Bay Maritime Museum is a must for history buffs. Whether it’s boating, enjoying fresh seafood, or browsing art galleries, St. Michaels offers a delightful mix of culture and natural beauty.
8. Monkton
Monkton is a rural town that’s surrounded by beautiful countryside, making it an excellent place for outdoor activities. You can explore the Northern Central Railroad Trail or take in the stunning topiaries at Ladew Topiary Gardens. With its calm and peaceful setting, Monkton offers a perfect escape from busy city life.
9. Leonardtown
As one of Maryland’s oldest incorporated towns, Leonardtown is known for its colonial architecture and scenic waterfront along Breton Bay. It’s also a hub for the arts, with local galleries and events throughout the year. The town’s antique shops, cozy cafes, and waterfront attractions make it an ideal spot for a leisurely visit.
10. Pocomoke City
Located near the southern border of Maryland along the Pocomoke River, Pocomoke City is a small town rich in history. The Delmarva Discovery Center highlights both the region’s colonial and natural history, while the town itself is filled with historic buildings and peaceful parks. Visitors can enjoy exploring unique shops, riverside parks, and enjoying a slower pace of life.
Maryland’s small towns may often be overlooked by travelers heading to the big cities, but these 10 charming towns prove that there’s more to discover beyond the well-known destinations. From mountain retreats to riverside escapes, these towns offer a glimpse into Maryland’s history, local culture, and natural beauty. If you’re seeking a more relaxed and authentic experience, these underrated gems are waiting to be explored.
Sources
[1] https://traveltriangle.com/blog/small-towns-in-maryland/
[2] https://www.pods.com/blog/best-small-towns-maryland
[3] https://www.attractionsofamerica.com/travel/most-beautiful-small-towns-maryland.php’
[4] https://www.worldatlas.com/cities/the-7-can-t-miss-towns-in-maryland.html
[5] https://www.hotels.com/go/usa/must-visit-small-towns-maryland
