Seven Spring Getaways in Maryland’s charming towns

Cumberland, Solomon’s Island, Leonardtown, Savage, Thurmont, Chestertown and Westminster

Are you planning a spring getaway? Maryland has so much to offer, whether you’re looking for time on the water, historic sites, country roads, adventure and outdoor recreation, educational activities for the family or a romantic escape. Here are seven charming Maryland towns worth a visit.

Downtown Cumberland Maryland has distinctive brick architecture and a central square.

Cumberland, on the tip of Western Maryland, is an architecturally beautiful red brick town surrounded by mountains and a wildlife sanctuary. Nicknamed “the Mountainside of Maryland,” downtown Cumberland has shops and casual restaurants, along with Appalachian crafts for sale at Mountainside Creative art coop. Also, downtown is the Allegany Museum which covers the pre-history of this region, with exhibits on the Ice Age, Native Americans and frontiersman. The town was a strategic location used by George Washington during the French and Indian War, and his well-preserved cabin is worth checking out. Another reason to chug to Cumberland is for the 30-mile ride on the Western Maryland Scenic Railroad through forested mountain vistas. If you’re looking for adventure, head over to Adventure Sports Center International for a heart pumping white water raft trip or rock climbing expedition. Stay at the Rocky Gap Casino Resort, where you can mix gambling, golf, spa treatments, live performers, with nature walks and hiking.

Solomons Island has a waterfront pier with shops and restaurants, where it’s fun to watch the watermen come in to unload fresh caught seafood.

Solomon’s Island, in Southern, Maryland is a quaint fishing town blessed with miles of coastline on the Chesapeake Bay, and to get to this picturesque waterfront region, you don’t have to cross the Bay Bridge. Solomon’s legendary Tiki Bar hosts outdoor happy hour every evening where you can watch the watermen return to the dock with their catch of the day. Visitors can learn the seafaring history of the Early American colony, one of the first to be settled in America, with a visit to the Calvert Marine Museum. Other highlights include Stoney’s Solomons Pier, a mile long boardwalk, or tour the two historic lighthouses, Piney Point and Point Lookout. Nature lovers can comb the beaches of Calvert Cliffs or Flag Ponds Nature Park for fossils and sharks teeth. Stop in one of the many waterfront restaurants for local seafood or Solomons Island Winery’s downtown tasting room. For adventure, hop aboard a sailing cruise with Chesapeake Bay Charters or learn how to sail with Sail Solomons.

Patuxent River Naval Air Museum in Leonardtown Maryland

Leonardtown in St. Mary’s County is located in the Maryland Tidewater between the Chesapeake Bay and the Patuxent River. Considered the birthplace of Maryland, the region dates back to the 1500’s when it was a tobacco port. Downtown Leonardtown has some independent retailers, an arthouse movie theater, a winery, brewery and restaurants featuring local seafood. The town is best known for its annual Oyster Festival in October. For those seeking adventure, visit downtown Leonardtown’s Breton Bay Waterfront Park where you can launch kayaks and boats. The area also offers attractions, like Piney Point Lighthouse, which was integral to the protection of Washington DC in the war of 1812, as well as the Patuxent River Naval Air Museum, which showcases Navy airplanes from every era. There’s a weekly farmers market where local Amish farmers sell their homemade products, and you can visit an Amish creamery to see how they make cheeses without using any machinery! Just 10 miles from downtown Leonardtown is historic St. Mary’s City, a historic site where visitors can learn about the 16th century settlement, learn about efforts to preserve the community and learn about the archeological research. The living history actors speak the dialect of the times, welcoming visitors to watch and learn the practices of English colonists and Native Americans. Visitors can also board The Dove, an authentic ship from the late 1600s.

Savage Mill in Howard County has fabulous shops with antiques and locally made arts and crafts. There’s also a brewery and restaurant in the complex.

Savage, in Howard County, Maryland is best known for the historic Savage Mill, which milled cotton in the 19th century and now functions as the town gathering space, with shopping, dining, brewery, winery and community of arts and antique sellers. Located in this complex on the scenic Savage River, you can catch a variety of bands at Ram’s Head Tavern or go zip lining at nearby Terrapin Adventure Park. The scenic iron truss bridge, the town’s most memorable landmark, leads to acres of parkland. Just a few miles away is Jailbreak Brewing Company with its new FoodWorks food hall. Adventure Seekers love the Autobahn Speedway where they can race around an indoor track at up to 50 mph. Families favor visiting the Clark’s Elioak Farm with its petting zoo, tractor rides, and vintage enchanted forest containing life sized characters from nursery rhymes. Art fans adore the ManneqART Museum displaying quirky mannequins wearing creative costumes. Also, down the road is the NSA’s Cryptologic Museum where you can learn the history and techniques used to develop and break codes. This STEM hub is surrounded by the University of Maryland Astronomy Observatory, Dinosaur Park, Patuxent Research Refuge, as well as NASA Goddard Space Flight Center, where you can take an informative tour and see a collection of rockets.

Sailing on the Chesapeake Bay is a popular activity in Chestertown, Maryland

Chestertown, in Maryland’s Eastern Shore dates back to Revolutionary times and is considered one of the best preserved colonial-era villages in the country with its historic Courthouse, Town Hall and Fountain Park. Just steps from downtown are two lovely waterfront parks from which daily sightseeing cruises depart in good weather. The town decorates for every holiday, and locals spend oodles of time outdoors. Chestertown is all about festivals and fun, like the annual Tea Party Festival and Parade, the Dickens Christmas events, or the Classic Cars Show. Visitors looking for adventure can explore the secluded coves and waterways in kayaks, or  ride bikes around the quiet roads flanked by farmland. This historic community has a busy farmers market, and the restaurants are known for serving the bounty they source from local farms and watermen. Once a wealthy community, the graceful Victorian mansions are a good reason to take a walking tour in Chestertown. The town skews young, thanks to the campus of Washington College and a classic Chestertown experience is sailing aboard The Sultana where you can learn to navigate the Bay and try your hand at trimming the sails.

Thurmont has exceptional hiking nearby including the beautiful Cunningham Falls.

Thurmont may be the cutest small town you’ve never heard of. Probably because it’s the clandestine location for Camp David, the Presidential Retreat in Central, Maryland. Located at the foothills of the Catoctin Mountains, the charming town is the gateway to Cunningham Falls State Park with its gorgeous waterfalls and access to the Appalachian Trail. Just fifteen minutes north of Frederick and about thirty minutes south of Gettysburg, the town has a charming Main Street featuring shops with antiques and art. The downtown farmers market sources produce from dozens of fruit and vegetable farms surrounding the town. Springfield Manor Winery and Distillery in Thurmont is best known for its Instagram-perfect Lavender Festival, and the Catoctin Breeze Vineyard has a sprawling farm and outdoor patio with acres of grape vines. Take a ride along the historic Thurmont Trolley Trail, a paved path perfect for biking. Or download a driving tour to the area’s three picturesque covered bridges. Families love exploring Old Mink Farm with its petting zoo and hay rides, as well as taking a safari ride at the Catoctin Wildlife Preserve. In addition to offering hikers a wide array of challenging trails, visitors can also swim and rent kayaks at Cunningham Falls Lake. Every March, Thurmont hosts their annual Maple Syrup Festival celebrating its 50th anniversary in 2020.

Carroll County Agricultural Farm is a fun place to take kids to learn about this history of farming. It’s near the town of Westminster, Maryland.

Westminster, Maryland is located in the agricultural plateau of Western Maryland about 30 minutes west of downtown Baltimore. This small town has a very progressive vibe thanks to the artsy students at McDaniel College. Main street Westminster has coffee bars, bakeries and casual restaurants along with independent boutiques. Just outside of town is Westminster Winery, Pub Dog Brewery and Baugher’s Orchard and Farm (which also has a vintage diner with homemade comfort food). The most notable attraction is the Carroll County Farm Museum with interactive exhibits on the history of farming dating back to frontier days. Westminster has a number of national historic sites constructed around 1800; like Westminster Town Hall, Sherman-Fisher-Shellman House, Cockey’s Tavern, and the Historical Society’s Museum and bookstore. Looking for culture? Check out the live music at Rob’s Bluegrass Lounge or enjoy live theater at the Carroll Arts Center. Those seeking adventure can go horseback riding and zipling at the nearby River Valley Ranch. Westminster is best known for hosting the annual Maryland Wine Festival in September with 20 curated wineries, 4 nearby creameries, and 50 craft and food vendors. In spring, catch the parade celebrating Westminster’s annual Irish Festival or attend the annual Peep Show with 150 marshmallow masterpieces on display, along with sweet treats to try and buy.   


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Freelance writer and photographer specializing in vivid, deeply reported stories about food, travel and family.

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