Most Underrated Towns in Maryland
Maryland is chock full of history and culture, as well as beauty and charm, which makes it worth the visit. The state sits amidst the dense forests of the US and along the coast of the Atlantic Ocean, meaning there is plenty to see and do.
While there are many beautiful cities to tour through–and maybe even retire to–in Maryland, there are a number of exciting and charming towns to explore. Here's a list of the most underrated towns you need to visit in Maryland.
Berlin
Some towns require time to develop into their best version. Berlin, founded and used as a plantation as early as 1677, has evolved into a hub of vibrant flavor and character. Located just five miles from Maryland's Atlantic coast, its 5000 residents have arranged their community so that the main street features a collection of brick storefronts.
The preservation of history is especially important here, where three eras of American history—Federal, Victorian, and 20th Century—are on display. Visiting in late September is perfect, as the lively Berlin Fiddlers Convention kicks off with live bluegrass concerts. This Berlin might not be the capital of Germany, but it is Maryland's true crown jewel of charm.
Chestertown
Located in Kent County, Chestertown was established in 1705. It played a significant role during the Revolutionary War, notably hosting a minor tea party rebellion, which is celebrated annually at the Chestertown Tea Party Festival. This event features a reenactment of the protest against British tea taxes and includes colonial crafts and performances throughout the weekend.
Chestertown is also home to Washington College, which was established in 1782 and is the tenth-oldest college in the United States. The college's Literary House serves as a center for literature and creative writing, hosting numerous public events annually, including the Sophie Kerr Prize, the nation's largest undergraduate literary award.
Furthermore, the town is situated along the Chester River, offering plenty of opportunities for kayaking, bird-watching, and other outdoor activities. The waterfront features several 18th-century Georgian-style buildings, cementing Chestertown as a refuge for the dreams of our ancestors and the visitors who observe them.
Thurmont
Located in the northern part of Frederick County, Thurmont sits at the foot of the Catoctin Mountains. The town provides direct access to two significant nature reserves: Catoctin Mountain Park and Cunningham Falls State Park. These parks offer hiking trails, camping facilities, and the 78-foot Cunningham Falls, the largest cascading waterfall in Maryland.
Thurmont has a renowned apple-growing industry, and the town widely celebrates its agricultural heritage with the Catoctin Colorfest every October. Additionally, the town is home to the Springfield Manor Winery and Distillery, which offers local wine and spirits tastings—a perfect way to unwind after a long day of sightseeing.
St. Michaels
Located on Maryland's Eastern shore, St. Michaels is home to a scenic harbor and the Chesapeake Bay Maritime Museum. The small town is the ideal location if you're curious about the state's maritime history, or if you want to indulge in activities such as sailing, kayaking, golfing, and bicycling.
Nestled in the harbor, the town's seafood and waterfront restaurants are something you can't miss. And if you pay a visit during winter, be sure to check out the town's Christmas celebrations. You can explore the many boutiques and gift shops and relish in the jolly spirit of the Christmas village.
Bel Air
Located in Hartford County, Maryland, Bel Air is celebrated for its vibrant arts scene and historic armory. The armory park features beautifully landscaped gardens, benches ideal for relaxation, and a stage area for various performances.
Stop off at Bel Air and pay a visit to one of the town's many concerts, art galleries, or memorable holiday cultural events. You can also enjoy a self-guided public art tour and visit 23 different sculptures and murals.
Chesapeake City
It's no surprise that Chesapeake City–actually a small town–is situated on Chesapeake Bay. The town is on the National Register of Historic Places as it bridges the bay and the Delaware River, operating as a commercial canal.
Most of the town's 19th-century architecture still stands, and visitors can also enjoy dining and nightlife, trails, water cruises, boutiques and shops, and more! And if you'd like to stay a little longer, check out one of the cozy bed and breakfasts.
Oakland
A visit to Oakland, Maryland, consists of walking trails, parks, shopping trips, and events and festivals. The beautiful outdoor locations are perfect for picnicking, adventuring, and time well spent.
The town also boasts a vibrant art scene where visitors can enjoy different sources of entertainment, ranging from galleries to musical events and plays. And if you've got an inkling to shop, check out Maryland's main street.
Finally, don't forget the Historic District, where you'll find beautifully restored Victorian buildings.
Vienna
Located on the Nanticoke River, Vienna is one of the oldest colonial settlements in Maryland. It is known as a historic waterfront town as it boasts access to a 1768 Customs House, the Vienna Heritage Museum, as well as a waterfront park.
With an abundance of inns and bed and breakfasts to choose from, you can stop in for a weekend or take your time and enjoy the historical and cultural stories of the town.
Leonardtown
Leonardtown is home to picturesque landscapes and waterways, as well as historic buildings, specialty shops, galleries, and scrumptious restaurants. Visitors will also find a quaint town square that is charming and walkable, ideal for a relaxing visit.
If you do visit, don't forget to check out the town's art scene, including one-on-one art classes and entertaining shows. It's also the perfect spot to visit during the holidays, with a beautiful tree lighting ceremony, meetings with Santa, and more.
Visit These Towns and Be Mary(land)!
It's safe to say that Maryland is home to a plethora of unique small towns ideal for weekend adventures and exciting getaways. Whether you're interested in picturesque views, outdoor activities, delving into the history, or everything in between, add these small towns to your bucket list.
There's plenty to explore and see, and the only thing that will make your trip better is if you check out more than one!
