Aerial still image of the town of Boonsboro, Maryland, taken by a drone on a Fall afternoon.

8 of the Quirkiest Towns in Maryland

Although Maryland is famous for its natural beauty, scenic coastal areas, and captivating Civil War history, it is also home to an exciting mix of quirky towns that defy the norm and intrigue visitors. Beyond the well-known cities stealing the spotlight, hidden communities with unusual cultures and odd attractions showcase their uniqueness. These promise a fresh experience for those who prefer off-the-beaten-path adventures.

Whether you're seeking curious gems that go beyond the ordinary or hoping to embrace the weird during your Southern retreat, the quirkiest towns in Maryland have all it takes to guarantee a remarkable experience. Set the stage for an unconventional holiday in the Old Line State with these strangely interesting towns.

Savage

Station Six, built on Corridor Road in Savage, Maryland
Station Six, built on Corridor Road in Savage, Maryland, By Mwschaef - Own work, CC BY-SA 3.0, Wikimedia Commons

There is nothing savage about the community inhabiting this tiny Howard County village, located about 18 miles from Baltimore. Instead, you can look forward to friendly locals inviting strangers to take advantage of their diverse tourist offerings. The town boasts beautiful outdoor spaces if you love being one with nature, such as the picturesque Savage Park. With nearly 3 miles of trails, you can revel in the peaceful atmosphere during a leisurely walk and relax at its picnic pavilion while enjoying the scenery. But if you want to up the ante, it doesn't get better than Terrapin Adventures. This awesome local outfitter keeps your adrenaline flowing with thrilling activities like zip-lining, whitewater tubing, giant swinging, and tower climbing.

Savage houses its fair share of historical gems that will intrigue enthusiasts who come across them. The Carroll Baldwin Hall is just one of them. It was founded in 1920 for the welfare of the Savage community. Today, it hosts various educational, social, and recreational activities. Elsewhere, the Bollman Iron Truss Bridge is a noteworthy town landmark, considered one of the country's oldest functioning iron railroad bridges.

Funkstown

View east along U.S. Route 40 Alternate (Baltimore Street) between Westside Avenue and Antietam Street in Funkstown, Washington County, Maryland
View east along U.S. Route 40 Alternate (Baltimore Street) between Westside Avenue and Antietam Street in Funkstown, Washington County, Maryland, By Famartin - Own work, CC BY-SA 4.0, Wikimedia Commons

Funkstown compensates for its low population numbers with diverse and whimsical attractions that give the town a "funky" vibe. This Washington County community is home to fewer than 1,000 residents but promises tourists no shortage of excitement. Highlights include Funkstown Community Park, a popular public gathering space where you can find sporting opportunities such as tennis, baseball, and basketball. The venue also hosts seasonal Civil War reenactments that will interest United States historians. Alternatively, you can take a leisurely stroll through the tranquil downtown area and discover gems like Joker's Bar & Grill, an excellent spot to mingle and interact with the locals in a cheerful atmosphere.

For those with a taste for freshly crafted wine, a visit to Blue Mountain Wine Crafters is a must, offering the opportunity to sample the best local wine offerings while enjoying live music. Also, don't forget to stop by The Vintage Attic to hunt for a charming souvenir from your time in Funkstown. It boasts a brilliant selection of items, from vintage farmhouse decor to antique furniture.

Hancock

Downtown Hancock, Maryland.
Downtown Hancock, Maryland. Image credit Alejandro Guzmani via Shutterstock

Hancock's uniqueness stems from its location in the narrowest section of the state. This Washington County town is also home to a community of bikers and hippies that contribute to its distinctive vibe. Several hangouts in Hancock offer a peaceful space to sit and enjoy observing the activities around you, including Joseph Hancock Jr. Primitive Park. This modest park provides camping opportunities and features a small pavilion accommodating 30 to 40 individuals. Alternatively, you can visit the Sideling Hill Welcome Center to pick up informative brochures that will guide you to the best places to explore in Hancock.

The downtown corridor is an interesting neighborhood with a nice mix of shops, restaurants, antique malls, and other businesses. One of the best stops is Buddylou's Eats Drinks & Antiques, which offers ample outdoor seating and serves delicious sandwiches and refreshing craft beer.

Berwyn Heights

In Berwyn Heights, Maryland, a historic house at 5617 Ruatan Street
Berwyn Heights, Maryland: a historic house on Ruatan Street, By geraldshields11 - Own work, CC BY-SA 3.0, Wikimedia Commons

Some people have dubbed Berwyn Heights the "UFO Capital of Maryland" due to claims of sightings by locals. While there is no guarantee you will witness extraterrestrial activity in the town, you can look forward to numerous exciting outdoor opportunities. Several idyllic natural spaces, including Lake Artemesia Natural Area, invite adventurers to make the most of the open spaces. The same applies to Greenbelt National Park, Lake Artemesia, and the Anacostia Trails system, which provide outdoor enthusiasts with year-round hiking, biking, and nature viewing opportunities.

In addition to its outdoor pursuits, College Park offers exciting indoor activities with venues like the College Park Aviation Museum. Dubbed the oldest continuously operating airport in the world, this quaint facility houses several galleries with exhibits celebrating various aviation milestones. Alternatively, you can break a sweat by playing a competitive tennis game at the College Park Tennis Center.

Boonsboro

Historic buildings in downtown Boonsboro, Maryland
Historic buildings in downtown Boonsboro, Maryland

Unusual roadside sculptures make Boonsboro one of the quirkiest towns in Maryland. But there is more to this laid-back rural locality that will interest visitors, especially those with a soft spot for nature. Boonsboro is home to Greenbrier State Park, a recreational hub with hiking, camping, and nature viewing opportunities. The park also features a 42-acre reservoir where you can go swimming, boating, or fishing. Meanwhile, South Mountain State Park lets adventurers explore the town's wilderness through hiking, mountain biking, and horse riding excursions. It also boasts natural wonders, including a stunning 80-foot waterfall.

When you're not exploring the open spaces, you can stroll through the beautiful downtown corridor to discover its offerings. Noteworthy venues like the Boonsboro Museum of History provide insights into the town's storied past through a broad collection of artifacts chronicling historical events. The same is true for the Boonsboro Historical Society, which enhances your historical experience with a focus on two Civil War battles.

Poolesville

Poolesville, Maryland: Llamas enjoy a sunny afternoon at Homestead Farm during its annual Pumpkin Festival.
Poolesville, Maryland: Llamas enjoy a sunny afternoon at Homestead Farm during its annual Pumpkin Festival, via Nicole Glass Photography / Shutterstock.com

Poolesville's whimsical sculptures and eccentric boutiques liven up the unique vibe of this tiny Montgomery County town. However, that is not what makes Poolesville appealing to visitors. The town charms with numerous green spaces that allow you to experience the beauty of Maryland's backcountry, providing a quiet escape from the chaos of nearby Washington, D.C. These include Whalen Commons, which serves as the focal point of Poolesville's activities, drawing locals and visitors alike to enjoy its green spaces. Another excellent venue for outdoor lovers is EE Halmos Park, which offers various recreational amenities, including a basketball court, baseball fields, and tennis courts.

While exploring the outdoors, you can discover a historical gem at Riley's Lock, which is a part of the Chesapeake and Ohio Canal. Afterward, you can relax with a dip in the cool waters of the Sarah E. Auer Western County Outdoor Pool.

Chestertown

A residential street in historic Chestertown
A residential street in historic Chestertown, via George Sheldon / Shutterstock.com

Chestertown stands out for its vibrant art scene, with multiple art venues at nearly every street corner. This peaceful Kent County town is tailored for creativity and delights with attractions like the MassoniArt Gallery. Here, you can browse a fine collection of exhibits by artists from the Mid-Atlantic region. The Garfield Center for the Arts at the Prince Theater is a popular community art venue worth checking out, celebrating the arts by staging exciting live performances. But when you've had your fill of the cultural experience, you can explore the town's history at the Historical Society of Kent County.

The facility preserves Chestertown's past by displaying documents, artifacts, and other relics associated with the community. For outdoor enthusiasts, Wilmer Park offers a more enticing prospect and provides a mix of opportunities, including a picnic pavilion for loungers and sightseers, a playground for kids, and kayaking excursions along the Chester River for those seeking water-based fun.

Hagerstown

Street view in Hagerstown, Maryland
Street view in Hagerstown, Maryland

Just beyond the rolling hills of western Maryland lies the lively city of Hagerstown. With centuries of unique history, the town safeguards a treasure trove of interesting tales within its museums. You can glimpse the town's past at places like the Hagerstown Roundhouse Museum and feel the engrossing vibrations of yesteryear. For young adventurers curious to learn, the Discovery Station has hands-on puzzles to intrigue even the most seasoned scholars. It also presents interactive exhibits that stimulate young minds and educational displays that ignite the thirst for knowledge.

Hagerstown is blessed with natural beauty that beckons enthusiasts to explore its open spaces. You can follow the C&O Canal through hidden nooks and crannies to discover interesting natural surprises. Cyclists and hikers can traverse the terrain, surrounded by Mother Nature's splendor. Meanwhile, less strenuous adventurers can explore the diversity of Hagerstown City Park, a serene sanctuary teeming with wildlife and infused with human spirit.

Final Thoughts

The Old Line State has a wealth of history to explore but also offers unique experiences. The quirkiest towns in Maryland showcase the diversity of this fascinating Mid-Atlantic state and prove that the unusual can be exciting. While others gravitate towards Maryland's captivating history and spectacular coastal scenery, there is no harm in being drawn to its oddities and peculiarities.

Share
  1. Home
  2. Places
  3. Cities
  4. 8 of the Quirkiest Towns in Maryland

More in Places