10 Underrated Small Towns to Explore in Maryland
Adorably called “Little America” and “America in Miniature,” Maryland is a popular travel destination for tourists who want a bite-size taste of the United States. Its location in the Chesapeake Bay area and its significance in American history also make it quite a desirable vacation spot!
However, travelers often go to the state’s big cities like Baltimore or Columbia or opt for the popular quaint towns of Annapolis and Smith Island. If you want something new for your next Maryland trip, try some of its hidden gems instead! Here are 10 underrated small towns to explore in Maryland that can show you a different side of the state but still bring in the quintessential mini-U.S. experience you are looking for.
Frostburg
With a tagline “It’s just cooler here”, Frostburg is a fun niche location in Maryland for its iconic train and depot, museums, and other historic spots downtown. Experience a train ride with a great view via the Western Maryland Scenic Railroad. You will start at the Frostburg Depot and go through the Great Allegheny Passage.
If biking is more your thing, pedal away through lush trees with Tracks and Yaks. Back in town, visit the Thrasher Carriage Museum to learn more about vintage horse-drawn vehicles and the Frostburg Museum to get educated about the town’s history. In downtown, the Palace Theatre is a 1900s cinema, while the Princess Restaurant is a Frostburg icon visited by President Truman and his wife. See if you can get lucky and be seated at the Truman Booth!
Berlin
Boasting its Western theme park, fishing pier, unique museum, and historic commercial district downtown, Berlin is one of the best places in Maryland for a family-friendly vacation. Round up the family for a rootin’-tootin' time at the Sun Outdoors Frontier Town, a theme park replica of an 1880s Western Town. Pan for gold, ride ponies, and watch professional rodeos and gun fights. You can even witness bank holdup demonstrations!
Watersports fans can also rent jet skis through Frontier Town, while avid fishers can go with Lucky Break Charters for boats. The Mermaid Museum is a fun stop that will add a little mermaid magic to your little one’s trip. If you would rather do some downtown meandering and shopping, Berlin has 60+ shops that are mostly housed in late-19th-century buildings. Enjoy a classic 1901-era American diner with fountain soda at Rayne’s Reef, browse antique souvenirs at Outten’s Delites, wind down at the hip farm-to-table tavern at Blacksmith, and stay at the Victorian-era Atlantic Hotel to be close to all the downtown Berlin happenings.
Chestertown
Chestertown is a little historic port-town-turned-college-town in Kent County. Start with a selfie at Fountain Park, where the town’s iconic fountain with a Goddess Hebe centerpiece can be found. Then, hightail it to the visitor center, considered to be Chestertown’s gateway, to narrow down what you should see, do, and eat while in town.
For something free, do a self-guided walking tour to see Chestertown’s historic downtown. Art lovers should stop by the Garfield Center for the Arts or at Hegland Glass to see glass artistry and unique souvenirs. Want a taste of Chestertown fare? The Kitchen at the Imperial is known for its famous chef and fresh seafood. Chestertown has yearly signature events, like the Chestertown Tea Party Festival during Memorial Day Weekend, Paint the Town in early summer, and Dickens of a Christmas every December. Time your trips to visit during these events!
Leonardtown
Locals of this Southern Maryland town are proud of their lively wharf, art culture, and historic downtown and square. Head to Leonardtown Wharf to paddle, kayak, cruise along McIntosh Run, or rent boards and boats through Patuxent Adventure Center. The wharf had The World’s Largest Rubber Duck last year—a good sign for a repeat appearance in future wharf fests.
Leonardtown is also the only art district in Southern Maryland, thus having a wellspring of fun art classes and events, such as paint-and-sip parties of Wine and Design and wood sign workshops from Board and Brush. Shopaholics who love to support local businesses can drop by Shepherd's Old Field Market, Leonardtown’s marketplace for local shops, artists, and crafters. Interestingly, Leonardtown’s visitor center is attached to the Old Jail Museum, an interesting yet macabre look at Maryland’s past.
Thurmont
Among the underrated small towns to explore in Maryland, Thurmont is the perfect destination for travelers who love the outdoors. Known as the “Gateway to the Mountains,” the nearby Catoctin Mountain offers a plethora of hiking trails and campgrounds, with Chimney Rock, Wolf Rock, and the Blue Ridge Summit Overlook as some of its must-see spots.
If you would rather be a downtown explorer, Thurmont also has a wealth of Main Street attractions, such as the Thurmont Trolley Trail, the hearty eats of Thurmont Kountry Kitchen, and the watering hole of 10Tavern. A little way from downtown is the Roddy Road Covered Bridge, the smallest covered bridge in the county, which also has a nearby park for picnics and fishing. Venture further north from there to visit the picturesque Catoctin Breeze Vineyard, where you can sip and unwind to your heart’s content!
North East
For a serene small-town Chesapeake Bay experience that is still filled with watersports, museums, and seafood feasts, make North East your next stop in your Maryland trip. The North East branch of Chesapeake Water Tours can give you great options for sunset cruises, sightseeing tours, private charters, and even a Ladies’ Night cruise. Meanwhile, Bay Venture Outfitters handles kayaks and paddleboard rentals.
The town also houses the Upper Bay Museum, which showcases Maryland’s history and traditions of fishing and boating. After an afternoon of museum fun, stretch your legs at the nearby park before heading to Nauti Goose Restaurant for a night of crab cakes and waterfront dining! For more information on North East tourism, visit the Cecil County Tourism near the town’s pier.
Havre De Grace
Havre de Grace might be the sweetest out of all the underrated small towns in Maryland due to its charming parks and museums and scenic waterfront views. Begin your visit with a picture and a tour of Havre de Grace’s iconic lighthouse—the Concord Point Lighthouse, the second-oldest lighthouse in Maryland. You will also get to see the surrounding park, promenade, and the lighthouse keeper’s house during the tour.
Then, take a look at the nearby Havre de Grace Maritime Museum for the town’s port and fishing history and the Havre De Grace Decoy Museum for some adorable wooden ducks! Visitors with boats can dock at Penns Beach Marina at Heron before venturing into Havre de Grace’s downtown. Get a handful of homemade candies at Bomboy's, watch a live performance at The Opera House, and enjoy a dinner of American surf ‘n’ turf at the waterfront restaurant of Tidewater Grille.
Chesapeake City
Chesapeake City is best known for its historic canal and 18th and 19th-century homes that have been turned into inns and restaurants. Originally named the Village of Bohemia, the city’s name change was due to the establishment of the Chesapeake & Delaware Canal, which you can learn more about at the C&D Canal Museum.
While an appreciation for its history is great, the best way to enjoy Chesapeake City is through its waterfront attractions. Stay at the Ship Watch Inn, which is the only accommodation with great views of the canal. The Bayard House Restaurant is an 18th-century house that was transformed into an elegant seafood spot in the city. Jog along the canal via the Ben Cardin C&D Canal Recreational Trail or watch the city from the waters with a cruise from M/V Summer Breeze.
Easton
Proud to be the “Cultural Capital of the Eastern Shore,” Easton’s tourist spots are a great mix of American history, art culture, and local culinary delights. Book a suite at the Tidewater Inn, a historic mansion steeped in lavish Easton history. Right across it are the Avalon Theater and Troika Gallery, home to Easton’s live performances and fine art.
Perhaps the biggest Easton event is the Waterfowl Festival, a three-day jamboree in November that celebrates the town’s history, love for the arts, and conservation efforts for the region’s wildlife. If you wish to celebrate Easton by dining your heart out, munch on some American eats at Doc’s Downtown Grille, satisfy your sweet cravings with Bonheur Ice Cream and Pie, or feast on some “rude” barbecue and burgers at Rude Food Co.
Brunswick
This delightful little Maryland town should be on your radar for its railroad history and festival. The Brunswick Heritage Museum takes you on a journey to Brunswick’s past with its railroad memorabilia, interactive scale models, and Victorian costumes, to name a few. Come by every October to join the town in celebrating its Brunswick Railroad Days—a two-day festival that is all about Brunswick’s heritage.
For outdoorsy folks, Brunswick’s proximity to the Potomac River makes it a great hub for camping and doing watersports. The Brunswick Family Campground is the perfect place for these outdoor activities. For foodie tourists, Beans in the Belfry—a restored-church-turned-restaurant—and the American and Middle Eastern cuisines of Potomac Street Grill are great options when you are in town.
From majestic mountains to stunning panoramas of the Chesapeake Bay, Maryland is blessed with wonderful cities and towns that are ideal as tourist vacation spots. Whether big or small, these towns offer a cornucopia of attractions to local and foreign tourists hoping to experience the exciting tourism of the United States.
However, as seen by this list, there are highly underrated small towns to explore in Maryland, so you do not have to join the throng of tourists in the oft-visited cities. Frostburg’s historic railroad, Thurmont’s outdoor activities, and Havre de Grace’s lighthouse tours are just some of these underrated spots. Get to know Maryland in these quaint but equally impressive towns!
