2025's Most Underrated Towns In Maryland

While top cities like Annapolis and Baltimore grab all the headlines regarding Maryland travels, the Old Line State is chock-full of unknown destinations that don't get the attention they deserve. Scattered between the undulating Allegheny Mountains to the west and the chilled-out Chesapeake Bay to the east, these hidden gems remain unfairly underexplored, perhaps because of their isolated settings or more famous neighbors. Nevertheless, this doesn't take away from their appeal, providing the ideal escape from the chaos and commotion in major metro areas. As remote work becomes more mainstream and travelers increasingly seek off-the-beaten-path experiences, these underrated towns in Maryland prove to be the ideal vacation destination in 2025.

Chestertown

Chestertown is often overshadowed by other top destinations on the Eastern Shore, such as the culturally rich Easton and the historically captivating Cambridge. Despite this, the community charms its visitors with a vibrant art scene. Enthusiasts catch captivating stage productions at the Garfield Center for the Arts, whose lineup of performances ranges from concerts and dramas to musicals. With ready access to the calm waters of the Chester River, guests can set on a remarkable boating excursion courtesy of the Chester River Packet Company. This easygoing cruise on a 1920s-style tour boat provides a unique perspective of Chestertown's beauty from the water.

Finally, tourists who want to delve into the community's past can find invaluable resources at the Historical Society of Kent County. The venue stores relics, documents, and archives that preserve and interpret the region's dynamic history.

Thurmont

For many travelers, Thurmont is just but a mere pitstop on their way to Pennsylvania. However, there is much to see and do in this adorable mountain town, which invites ardent adventurers to immerse in its rich wilderness. Almost 25 miles of trails thrust vacationers into the heart of the Catoctin Mountain Park, renowned for its rugged terrain and stunning overlooks. The reserve offers camping, fishing, rock climbing, and backpacking recreation against the scenic backdrop of the Blue Ridge mountains.

More opportunities await in the adjacent Cunningham Falls State Park, which features a 43-acre reservoir as its focal point. The park's highlight is a gorgeous 78-foot cascade, hailed as Maryland's largest cascading waterfall.

North Beach

North Beach is not the most famous Maryland town on the Chesapeake Bay, it is often outshined by St. Michaels and Cambridge. As tourists flock to the other cities, it serves as a blessing in disguise for North Beach, which enjoys a less crowded atmosphere. Regardless, the views are as satisfying as any other when strolling down the North Beach Boardwalk. This picturesque promenade has an eclectic mix of restaurants, shops, wine bars, and even a Friday night farmer's market.

Nature enthusiasts will enjoy the serene setting of Wetlands Overlook Park. This peaceful sanctuary provides a habitat for wetlands wildlife and migratory fowl, serving as the perfect spot for nature photography. If you love the big screen, North Beach welcomes you to join other movie lovers during its annual North Beach American Film Festival for screenings of the best domestic and international films. The event is scheduled for September 2025.

Crisfield

Crisfield's remote location on the southern tip of Maryland, near the Virginia border, robs many visitors of a chance to explore it. The adorable fishing village promises exciting boat tours for those who venture that far, allowing them to experience the majesty of the Chesapeake Bay through Experience Smith Island. This authentic boat excursion features local islanders as guides and explores the area's culture with stops at close-knit villages. Another exciting trip leads to Janes Island State Park, where 30 miles of water trails, pristine beaches, and isolated marshlands set the stage for off-beat adventures.

Meanwhile, Crisfield has a thriving Arts and Entertainment District, home to a colorful community of artists, writers, musicians, crafters, and other creatives. This is the perfect escape to discover the arts and culture scene. Alternatively, you can wait for the Tangier Sound Music Festival on May 24, 2025, for an even more immersive experience.

Brunswick

Brunswick is next door to Virginia, separated by the Potomac River, giving it an isolated setting that few travelers attempt to access. Nevertheless, it has a range of exciting attractions, especially for the outdoorsy tourists. Brunswick City Park offers several lush acres of grassy lawns and shady trees with winding paths suited for lazy strolls to let loose and unwind. Meanwhile, you can't miss out on the local brewery culture. Use the opportunity to sample local drafts by touring Smoketown Brewing Station, known for producing over 20 varieties of award-winning beers.

Brunswick has a rich railroad heritage that it tributes during the annual Brunswick Railroad Days. Scheduled for the first week of October 2025, this family-friendly celebration of the town's history brings together artists, crafters, performers, and vendors from the region, culminating in a fun day for all ages.

Grantsville

It would seem there isn't much to do in this tiny Garrett County village of less than 1,000, making it one of the most underrated towns in Maryland. However, Grantsville silences doubters with its respectable attractions, starting with Casselman River Bridge State Park. This 4-acre site hosts an 1810s bridge built as part of the National Road and provides picnicking and fly fishing opportunities. Adventurers can find additional room for play at the larger New Germany State Park. This 500-acre forested wilderness features 10 miles of trails and access to a 13-acre lake for swimming, angling, and paddling.

Beyond the great outdoors, Grantsville welcomes art lovers for a quaint culture lesson at Spruce Forest Artisan Village. This unique heritage center preserves the region's arts and culture through a quirky exhibition of pottery, sculptures, jewelry, metalwork, and other art forms. It also hosts workshops and demos for visitors to witness the intricate art-making prices.

Parkville

Parkville's proximity to Baltimore ensures most holidayers don't pay much attention to it as a vacation destination. While it may not be as flashy as its bigger neighbor, it is a great destination if you want a more natural setting. Outdoor lovers can bask in the green atmosphere of Double Rock Park, which spans 102 acres of recreational terrain, inviting them for mountain biking, hiking, and sports. Also, Cromwell Valley Park keeps the outdoor fun going with over 400 acres of space that is prime for birding.

Elsewhere, if you enjoy a good laugh, you can always stop by Sully's Comedy Cellar. The venue hosts acclaimed comedians from popular networks, including Comedy Central and the Last Comic Standing.

Laurel

Laurel is a short drive away from Columbia and Washington, D.C.; hence, it's no surprise that it remains overshadowed by the bigger cities. However, those who take a chance on it access serene outdoor areas like Granville Gude Park. This cozy oasis features two lakes, picnic tables, a boat ramp, a lakehouse, and boat rentals for the public's amusement. Laurel's history is well-preserved at the Laurel Museum, a vintage home built in the 1830s. It is a great spot to understand the local heritage and culture through engaging exhibits.

For a lovely cultural and culinary experience, you can try shopping at the Dutch Country Farmer's Market, which sells delicious eats from Dutch Country. Besides interacting with friendly local vendors, you get to savor fresh dairy products, homebaked goods, candies, BBQs, and more.

Final Thought

A trip to the Southern United States presents travelers with a long list of exciting destinations for a short retreat or long vacation. However, this also leaves many decent places underexplored that deserve as much attention. The underrated towns in Maryland highlighted above are a fraction of what guests are missing out on when they go for the big cities in the state. From the often-overlooked North Beach to the remote Crisfield, they make for enticing places to include in your 2025 itinerary.