Maryland's 9 Most Underrated Towns To Visit In 2025

From the foothills of the Allegheny Mountains and the shores of Deep Creek Lake to the beaches along the Chesapeake Bay, the Old Line State is home to many charming small towns that don't always get the recognition they deserve. While places like Baltimore and Annapolis see plenty of visitors yearly, several under-the-radar communities across the state are worth exploring. In 2024, consider heading off the beaten path to discover some of Maryland's most underrated towns.

Shielded from the hustle and bustle of the big cities, these hidden gems promise a relaxed retreat in the heart of the state’s backcountry. Each offers a taste of small-town charm, historic architecture, natural beauty, and local culture, making getting away from it all a delight. Whether visiting for a weekend getaway or a month-long vacation, here are some of the most underrated towns in Maryland to see.

Thurmont

Many tourists on a Midwest itinerary often make Thurmont a quick stop on their way to Pennsylvania, but this small village in Frederick County offers a range of exciting attractions to explore. The town features several historic covered bridges, highlighted by the mid-1800s Roddy Road Covered Bridge. This bridge crosses Owen’s Bridge and is surrounded by lush natural scenery, making it perfect for a picnic. Thurmont is also an adventure lover’s paradise, serving as a gateway to the Blue Ridge Mountains. Visitors can lose themselves in the expansive Catoctin Mountain Park by enjoying activities like fly fishing, hiking, biking, and cross-country skiing. 

Cunningham Falls State Park is better suited for guests interested in aquatic fun. The park’s crowning jewel, Cunning Falls, is Maryland’s highest cascading waterfall, dropping almost 78 feet. Tourists also enjoy diverse water-based recreations, from kayaking and swimming to boating on the 43-acre artificial lake in the park. If you have a soft spot for social events, you can target the 20th Annual Thurmont Business Expo on April 27, 2024, to interact with locals and learn about their products. 

North Beach

Popular destinations like Cambridge and Ocean City dominate conversations about beachside getaways in Maryland, but the hidden gem of North Beach offers just as satisfying an experience. A lazy stroll along the North Beach Boardwalk is among the go-to experiences in town, spoiling you with breathtaking water vistas, a laid-back atmosphere, and easygoing fishing opportunities. Further inland, North Beach houses a few green spaces that will appeal to nature lovers, including Wetlands Overlook Park. Home to migratory shore birds and wetland wildlife, the atmosphere is perfect for relaxing and wildlife viewing. 

The indoor inclined can find a perfect pastime inside the Bayside History Museum, exploring a collection of exhibits documenting the area’s natural and cultural history. Alternatively, they can sample the local art scene by catching an exciting live performance at the Twin Beach Players. 

Havre De Grace

Situated where the Chesapeake Bay meets the Susquehanna River, Havre de Grace offers scenic waterfront views and harbors a rich maritime heritage. It was named after a port town in France, and its name translates from French to "Harbor of Grace." You can explore the area's nautical roots at the Havre de Grace Maritime Museum, home to artifacts and exhibits focused on the local fishing and crabbing industries. Also, take in spectacular Atlantic views while walking along the Havre de Grace Promenade while watching for shorebirds. 

The Friends-Concord Point Lighthouse is an iconic city landmark from the early 1800s worth touring. It served a vital role in warning ships of the choppy waters ahead but now gives educational tours. Nearby, Susquehanna State Park provides outdoor recreation like fishing, hiking, and boating and a spacious campground ideal for immersing oneself in natural beauty. One of the best ways to explore the open spaces is to take a guided Nature Trail Walk along the scenic North Park Loop Trail on March 9, 2024, for an easy 1.5-mile hike. 

Boonsboro

Civil War enthusiasts can look forward to captivating gems in this historic town in Washington County. Famous for its role during the infamous conflict, Boonsboro maintains intimate relics and reminders of the great battles that played out within its borders. It is home to the rustic Washington Monument, built in 1827 in honor of George Washington. But for a deeper dive into the area’s colorful history, the Boonsboro Museum of History brings the town’s past to life through a vast collection of artifacts. 

Boonsboro also delivers a range of recreational opportunities across its many natural attractions. Campers, hikers, swimmers, and anglers assemble inside the expansive Greenbrier State Park to enjoy its fun activities. The same applies to South Mountain State Park, which houses 50 miles of trail and a stunning 80-foot waterfall. If you visit with kids, be sure to sign them up for the Annual Fishing Derby on May 4, 2024, for a fun family day out. 

Grantsville

The sleepy village of Grantsville may seem like any other dull small-town stop on your Maryland trip. However, this hidden treasure features several underrated state parks that immerse you in the state’s stunning wilderness. It is well known for the Casselman River Bridge State Park, with its highlight being the 80-foot historic Casselman Bridge, built between 1813 and 1814. Grantsville also includes the larger New Germany State Park, covering 483 acres and bordering the Savage River State Forest. This outdoor recreation area offers camping, hiking, fishing, paddling, and swimming opportunities. 

On May 11, 2024, the New Germany State Park will host the Wild Spirit Native Plants at the Mountain Maryland Native Plant Festival, an excellent opportunity to learn about local flora. After working up an appetite from exploring the town’s outdoor attractions, you can enjoy a wholesome meal while admiring local crafts at Penn Alps Restaurant & Craft Shop. Later, check into the landmark Casselman Inn for a rustic accommodation experience to cap off the day.

Mount Airy

Not many people know about this precious gem in Maryland's Western mountains. Mount Airy offers a respite from busy life with its beautiful countryside landscapes and small-town hospitality. Wine and beer lovers will find themselves in paradise, thanks to multiple local breweries and wineries crafting fresh alcoholic drinks. Black Ankle Vineyards provides the perfect starting point, surrounded by Mount Airy's rolling hills. Guests can enjoy a guided tour of the scenic property, stopping at the tasting room before settling in for a picnic. For craft beer enthusiasts, Milkhouse Brewery will make for the perfect alternative.  

Nature lovers will appreciate Mount Airy's peacefulness within the Audrey Carroll Audubon Sanctuary. Spanning over 100 acres, this serene oasis protects diverse wildlife, from hundreds of bird species to other forest fauna. Spring and fall are the best times to visit, allowing guests to help with monarch butterfly tagging and observe migratory birds passing through. Alternatively, you can schedule your visit to coincide with Mt. Airy Fire Company Carnival in July & August 2024 for an immersive cultural experience. 

Jarrettsville

Remember to bring a camera to capture the magic in this relaxed rural town in Harford County. Jarrettsville is renowned for expansive sunflower fields, which paint the city with rows of green and bright yellow, resulting in postcard scenery. You can visit Clear Meadow Farm Sunflower Field to revel in a serene atmosphere with fresh air and a lovely aroma. The sunflower farm stretches as far as the eyes can see, compelling nature photographers to keep on snapping away. 

Some Jarrettsville residents will argue that most visitors come to Rocks State Park. Covering 855 acres of rocky woodlands, the park is a popular recreation hub, offering hiking, rock climbing, fishing, and river tubing opportunities. Those looking for a less remote alternative can check out Dr. James B. Rutledge Memorial Park, which offers a more family-friendly setting with amenities like nature trails, a soccer field, and picnic areas. 

Emmitsburg

From a distance, Emmitsburg appears like any other small town in Maryland, but you need to visit it to uncover its rich historical heritage, vibrant culinary scene, and notable academic landscape. Home to Mount St. Mary’s University, Emmitsburg is a little gastronomic hub, offering a diverse range of restaurants that serve all kinds of flavors, from Southern-style cuisine and seafood to Italian dishes. Seafood enthusiasts can visit Rube’s Crab Shack to try the state’s famous crab dishes. Established in 1785, Emmitsburg is one of Maryland’s oldest towns and features a couple of historical markers. 

These include the Frederick County Fire Rescue Museum and the National Fallen Firefighters Memorial. The latter pays homage to gallant volunteer firefighters who lost their lives in the line of duty. Before leaving the town, consider visiting Emmitsburg Antique Mall to shop for unique treasures. 

Leonardtown

The small town of Leonardtown in St. Mary's County offers something for every visitor. Historians can explore the town's roots at landmarks such as Tudor Hall, a Georgian-style home built in the 1700s. Another interesting landmark to visit is Moll Dyer Rock, where a woman accused of witchcraft was sadly found frozen after the public confronted her. Meanwhile, nature enthusiasts can head to Leonardtown Wharf Park for kayaking, picnicking, and paddleboarding with locals. The waterfront area is the perfect place to enjoy the outdoors. 

After a tedious day of adventure, stop by The Front Porch to restock with sumptuous Southern fare, then unwind for the evening at the Inn at Leonardtown. With intriguing tales of the past and scenic natural beauty, Leonardtown packs plenty of unexpected charm into its tiny space.

Discover Maryland's Hidden Charms

From Western Maryland mountain towns to waterfront communities along the Chesapeake Bay, each of these Maryland spots offers a distinct charm. Whether you're into history, outdoor activities, local food, or just relaxing, they provide peaceful settings to enjoy the state's hidden treasures. By exploring off the beaten path in 2024, you'll see a more genuine side of Maryland through scenic countryside, friendly residents, and cultural highlights often missed by tourists. So consider venturing into new areas and visiting at least one of these underrated towns to discover why locals proudly call them home.