Aerial view of Chestertown on the Chesapeake Bay in Maryland.

9 Overlooked Towns In Maryland Worth Visiting

Maryland, also known as the "Old Line State" or the "Free State," boasts numerous amazing communities throughout the state that many people have come to know and love, including Baltimore, Annapolis, and Ocean City. However, there are plenty of overlooked communities with incredible local charm, fantastic restaurants and shops, and rich history that deserve some much-needed attention, as they often go unnoticed in favor of larger, more renowned communities that people tend to visit on long weekends or day trips. Each of these communities offers something unique to everyone, such as beautiful waterfronts, pristine natural surroundings, and proximity to major cities, making them a wonderful place to visit or potentially call home.

Hyattsville

Street view in the town of Hyattsville in Maryland. By Famartin - Own work, CC BY-SA 4.0, Wikimedia Commons.
Street view in the town of Hyattsville in Maryland. By Famartin - Own work, CC BY-SA 4.0, Wikimedia Commons.

Just north of Washington, D.C., is the city of Hyattsville, which may be overlooked due to its proximity to the nation's capital, making it part of the D.C. metro area. However, the city has all it takes to stand on its own with a wonderful arts scene in places like the Pyramid Atlantic Art Center, which specializes in paper-making, book art, and print art, and hosts the annual Hyattsville Arts Festival every September, which hosts about 100 local artists, craft-makers, food and craft beer vendors, and local musical entertainment.

Downtown has plentiful amazing restaurants, shops, and breweries, like Streetcar 82, which is named after the 82 Streetcar line that ran from 1888 until it closed in 1958, and is a deaf-owned business that is loved and respected in the community. Just west of downtown is the Hamilton Splash Park, a community waterpark with an aqua climbing wall, a water slide, and an affordable option for families wanting to relax on a hot summer day.

Leonardtown

Leonardtown, Maryland. Editorial credit: Alexanderstock23 / Shutterstock.com
Leonardtown, Maryland. Editorial credit: Alexanderstock23 / Shutterstock.com

Just on the Breton Bay is Leonardtown, another overlooked town known for its peaceful charm, robust arts scene, and natural beauty, thanks to its location on the bay. The Leonardtown Wharf is a serene spot to visit, offering a tranquil ambiance along the McIntosh Run and Breton Bay, while also hosting private events and weddings for a perfect weekend getaway.

Further inland is downtown, which boasts amazing local places to visit, including the Alice in Leonardtown Mural and Wine and Design, a local painting studio that hosts art classes and private parties, adding to the community's artsy ambiance. A local staple, the Fenwick Inn hosts weddings and other community events, offering charming pavilions and grounds for the perfect weekend getaway. Built in 1933, the venue is a testament to its rich history.

Chestertown

Chestertown, Maryland. Image credit: George Sheldon / Shutterstock
Chestertown, Maryland. Image credit: George Sheldon / Shutterstock

Tucked away on the banks of the Chester River is Chestertown, located on the eastern shore of the state, which often gets overlooked due to its limited major transportation options compared to the hubs of Baltimore and Annapolis. The Chestertown Marina is a spectacular place to explore the river, whether you use kayaks or boats, along with the adjacent Wilmer Park, offering charming views of the river and the surrounding landscape.

Further in town, visitors can stay in the charming White Swan Tavern, a historic bed and breakfast in a Colonial-era building near downtown. White Swan offers its guests a variety of amenities, including a warm breakfast, and is conveniently located near local restaurants such as The Kitchen at the Imperial and Bad Alfred's Distilling. A wonderful park to visit, located within walking distance of White Swan, is the iconic Fountain Park. It is home to the "Lady in the Park" fountain, situated in the heart of town, and is a perfect spot to enjoy on a peaceful, sunny day.

Frostburg

Frostburg, Maryland. By Lee Cannon - CC BY-SA 2.0, Wikimedia Commons.
Frostburg, Maryland. By Lee Cannon - CC BY-SA 2.0, Wikimedia Commons.

Frostburg, a lively college town on the western end of the state, is a community often overlooked due to its isolated location, despite Interstate 68 running through town. It is also known as a mountain town. An adventurous trail to explore is the Great Allegheny Passage. This 16.3-mile-long trail extends from town to Cumberland and is perfect for hikers, walkers, and bikers in the hilly and mountainous community.

The city is also rich in history, as the Thrasher Carriage Museum showcases historic horse-drawn carriages from the late 1800s and early 1900s, located across the street from the Frostburg Depot, a part of the Western Maryland Scenic Railroad. Another historic museum to visit near downtown is the Frostburg Museum, which further explores the history of the community and its founding. On top of that, the Frostburg Museum is within walking distance of amazing hotels, restaurants, and shops in town.

Boonsboro

Boonsboro, Maryland. By Acroterion - Own work, CC BY-SA 4.0, Wikimedia Commons.
Boonsboro, Maryland. By Acroterion - Own work, CC BY-SA 4.0, Wikimedia Commons.

Just west of Frederick is the historic town of Boonsboro, situated near Civil War sites such as Antietam and South Mountain, which hosted significant battles. Although Boonsboro lacks a booming commercial scene, the community more than makes up for it with its small-town charm and historical sites within its boundaries, including the National Road Museum, which educates its visitors about the first federally funded highway, and the last surviving trolley station in Washington County. Another museum to visit in the community is the Boonsborough Museum of History, which further explores the town's history and features artifacts from the Civil War on display.

On the Old National Pike, aka "Main Street," visitors and residents can explore local restaurants and shops like Rasco NY Pizza, the Sizzling Fajita, and the Pathfinder Farm Distillery Tasting Room and Cocktail Bar, as great choices for bites to eat. Next to a couple of these restaurants is the Inn BoonsBoro, where guests can enjoy their time in a relaxing space with great amenities in a historic building dating back to the town's origins.

Chesapeake City

Chesapeake City, Maryland.
Chesapeake City, Maryland.

Just south of Elkton on the Back Creek is Chesapeake City, a small town renowned for viewing ocean-going vessels inland on the Chesapeake and Delaware Canal. The canal itself was built in 1829 and connects the Delaware River and the Chesapeake Bay, carrying 40 percent of the world's sea traffic traveling to the Port of Baltimore. Tours of the canal are available through Chesapeake Water Tours, allowing people to enjoy time on the water while taking in the views of the community.

After exploring the water, people can enjoy wandering through Pell Gardens Park and taking in the view of Back Creek, followed by dinner at the Chesapeake Inn Restaurant and Marina, and a visit to Schaefer's Canal House on the other side of the creek. Downtown is quaint and charming, with numerous amazing shops, restaurants, and hotels, including the Ship Watch Inn, which offers its guests incredible views of the water and is conveniently located within walking distance of all the town's action.

Thurmont

Covered bridge in Thurmont, Maryland, in the fall.
Covered bridge in Thurmont, Maryland, in the fall.

Just east of the famous president’s hideaway, “Camp David,” is Thurmont, a town surrounded by forests and mountains, and it has been nicknamed "the Gateway to the Mountains." Known for its natural resources, visitors are treated to a wonderful array of parks, such as the Catochin Mountains, which boasts 25 miles of incredible trails to explore. Cunningham Falls State Park is another breathtaking park to explore, boasting the state's tallest waterfall and offering amazing spots for swimming and boating. However, swimming is permitted from Memorial Day until Labor Day.

Visitors and residents are treated to wonderful shops, art galleries, and restaurants, such as the Rebecca Pearl Gallery, 10Tavern, and Thurmont Kountry Kitchen. Other parks, such as Thurmont Square Park, are located in the heart of downtown, and the Thurmont Community Park is just a block away from downtown, yet still very accessible by car and on foot. Downtown may not be the only reason to visit, as there are abundant natural wonders to explore just outside of town.

Rock Hall

Hubbard's Pier restaurant in Rock Hall, Maryland. Image credit: Bryan Costin via Flickr.com
Hubbard's Pier restaurant in Rock Hall, Maryland. Image credit: Bryan Costin via Flickr.com

On the east side of the Chesapeake Bay is Rock Hall, a coastal community with fresh seafood, marinas, and a rich maritime history. Both the Haven Harbour Marina and the Spring Cove Marina give people access to exploring the Chesapeake Bay and maintain boats for the next journey on the water. Not too far from either marina is the Inn at Haven Harbour and the Spring Cove Inn, respectively. Both the Inn at Haven Harbour and Spring Cove offer charming amenities, wonderful breakfasts, and wonderful views of the Bay.

In the heart of downtown is the Rock Hall Waterman Statue, also known as the "Old Salt statue," further saluting the community's maritime history. Two bars to visit in town are the Flying Decoy Bar and Grill and the Rock Hall Brewing Co. Both restaurants offer amazing drinks, great-tasting food, and a memorable experience. Not too far from either restaurant is the Mainstay, where visitors and residents can enjoy live music in a charming local setting in the Kent County area.

North Beach

Homes on Chesapeake Bay, North Beach, Maryland, under a sunny blue sky.
Homes on Chesapeake Bay, North Beach, Maryland, under a sunny blue sky.

Just east of Washington D.C., and Landover is the coastal town of North Beach. The community competes with other beach communities, such as Chesapeake Beach and Rose Haven, but offers visitors and residents access to the Chesapeake Bay. It features a beach and Pier, where people can enjoy the sun and sand during the summer, fish at the North Beach Pier, and gaze at the sunrise and sunset. Visitors and residents can also enjoy the North Beach Boardwalk Pavilion, as it features bike paths, benches, and access to the beach. However, there is a $25 fee for non-residents of Calvert County to access the beach, and a $9 fee applies to Calvert County residents. In contrast, North Beach residents can enter for free with a beach pass.

Further inland, residents and visitors can enjoy delicious meals and great drinks at Neptune's Seafood Pub, the Wheelhouse Beer Garden, and City Sliders Steakhouse at the Westlawn Inn. Just next to City Sliders Steakhouse are the Guest Quarters at the Inn, where visitors to the community can rent spacious rooms, enjoy on-site amenities, and have access to excellent restaurants and shops in town within walking distance.

Final Thoughts

Each of these towns may have been overlooked, but they are truly remarkable hidden gems worth visiting for a stress-free weekend with friends or a solo trip. The communities deliver excellent experiences for everyone who visits, with glorious natural scenery ranging from mountains to beaches that will leave people speechless in their natural beauty. Amazing local shops, museums, and restaurants create the opportunity for endless memories and fun times for all. These nine communities are within driving distance of larger cities, making them decent choices for a day trip or weekend adventure. Choose one or more to visit, and they will no longer be overlooked.

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