6 Coolest Towns in Maryland for a Summer Vacation in 2024
Maryland is a cool state full of unique opportunities. It is one of the few places one can have a blast feasting on blue crabs, watching a bathtub race, and seeing wild ponies chilling on the beach, all in one day. Known as ‘America in miniature,’ thanks to its wide variety of things to do and see, Maryland is the perfect destination for this year’s summer vacation. With the warmer weather, visitors can take full advantage of Maryland’s many attractions - hiking the mountains, sailing the Atlantic Ocean, snacking at seafood festivals, or simply enjoying a sunny stroll through historic downtowns. Moreover, with many small towns showcasing these activities without the urban hustle and bustle, everyone should put Maryland on their summer 2024 vacation bucket list.
Berlin
Named ‘Coolest Small Town in America’ by Budget Travel, Berlin is a must-see stop for Maryland visitors. Visit in June to see the legendary Berlin Bathtub Races when local businesses zoom down Main Street in homemade rolling tubs. Also on Main Street, you’ll find the Calvin B. Taylor House Museum, which hosts live music on the lawn on Sunday evenings from June to September. In August, the museum is home to Berlin’s Peach Festival which celebrates the delicious fruit with music, kids activities, and a pie baking contest. If peaches aren’t your thing, there are plenty of tasty dining spots in Berlin. Check out Fins Ale House & Raw Bar - one of the stops on the Maryland Crab and Oyster Trail - where you can eat your fill of fresh oysters and locally caught crabs.
St. Mary’s City
Nestled on the shores of the scenic St. Mary’s River, St. Mary’s City is an excellent spot from which to explore Maryland’s unique history. The state’s first capital, this tiny town was founded in 1634 and is now a living history museum and National Historic Landmark. Summer is the perfect time to visit, with a full schedule of family-friendly events, including tours of the Godiah Spray tobacco plantation, workshops on 19th-century skills, and sailing adventures. Docked along the waterfront is the Dove, a reconstructed late 17th-century trading ship that’s open to the public and hosts navigation, knot making, and woodwork demonstrations.
Ocean City
Ocean City is a classic and cool Maryland beach town with sun-drenched boardwalks, golden beaches, and a relaxed, summery vibe. Summer is fishing season when anglers crowd into town for the Ocean City Tuna Tournament, Huk Big Fish Classic, and Tunas and Tiaras. If you’d rather eat fish than catch it, don’t worry; Ocean City has you covered. Stroll the 3-mile boardwalk to grab a bite of the local seafood and that other Maryland delicacy - saltwater taffy. Those with families can head over to the Jolly Roger Amusement Park, a sprawling waterpark that boasts 40 rides, 18 waterslides, go-kart tracks, and mini golf. For a totally different park experience, visit Assateague State Park, Maryland’s only oceanfront park. Located on Assateague Island, the park has two miles of beaches, hidden coves accessible by kayaks, and some exciting wildlife. Over 100 wild ponies live on the island, and summer visitors can see them with their foals, which are born early in the season.
Chesapeake City
The cool thing about Chesapeake City is that it’s the only town in Maryland situated on a working commercial canal. Completed in 1829, the canal was an important transport route connecting Chesapeake Bay with the Delaware River. With its roots as a key trading town, it’s no wonder Chesapeake City’s historic district is listed on both the National Historic Registry and Maryland’s Historic Registry. Check out the C&D Canal Museum to discover the fascinating history of the canal system, or visit the Turkey Point Lighthouse to enjoy stunning views over the Bay.
Visitors can experience the natural beauty of the canal firsthand on the Ben Cardin Recreational Trail. Popular with cyclists, hikers, and birdwatchers, the trail winds more than 15 miles to the Delaware River. Along the banks of the canal, one may be lucky enough to glimpse an otter or a bald eagle. From walking to wining, the Chesapeake Wine Trail is also a favorite. This vineyard tour covers 15 different wineries, and oenophiles can sip award-winning vintages while enjoying unforgettable views of Maryland’s Eastern Shore.
Thurmont
Vacation like a president in Thurmont, home to Camp David and some of Maryland's most stunning mountain scenery. This charming small town is the ideal destination for exploring the Catoctin Mountains, a section of the more well-known Blue Ridge Mountains. Visit the Cunningham Falls State Park to see the mountains at their best, with glorious trails and campgrounds perfect for hiking, biking, fishing, picnicking, and swimming. The nearby Catoctin Wildlife Preserve is a must-see for families and comes to life during the summer months in Maryland. This 100-acre zoo has a whole host of exotic residents, including panthers, zebras, monkeys, and bears.
St. Michaels
Located in Maryland’s Talbot County, St. Michaels is a quaint harbor town named one of America’s Top 10 Best Small Coastal Towns by USA Today. Here, history enthusiasts can find the Chesapeake Bay Maritime Museum, which documents the area's history from its roots as a small 1600s sailing colony to today’s tourist hub. The museum is also the departure point for the Patriot Historical Cruise, a gentle cruise along the beautiful Miles River that lets you view St Michael’s historic homes from the water. If you’re visiting St. Michaels in June, don’t miss the St. Michaels BrewFest, an annual festival for foodies that showcases the best of Maryland’s local craft beers and delicious cuisine.
Cool Maryland Towns for a Travel Bucket List
Maryland was the seventh state in the union, but it’s home to plenty of firsts - the first dental school, the first gas light, the first telegraph sent, and the first commercial ice cream factory all began here. If it's your first time in the Old Line State, it’s probably not going to be your last. Maryland’s gorgeous parks, stunning mountains, historic landmarks, and delicious dining bring visitors back year after year. And once you’ve seen it in summer, don’t miss it in winter when you can enjoy world-class skiing, snowmobiling, and skating. Maryland is a must all year round!
