7 Offbeat Towns to Visit in Maryland
One of the oldest of the US states – it was the ninth to join the Union in 1788 – Maryland certainly has a lot to offer those who enjoy offbeat travel destinations. Despite its diminutive size (it’s the ninth smallest state), Maryland is home to a surpassingly large collection of quaint small towns boasting unique attractions and fun things to do.
From the maritime heritage of Chesapeake Bay to the historical landmarks of old colonial America, these towns provide a mosaic of unique experiences that truly capture the heart and soul of the “Free State.” Whether planning a couples’ East Coast road trip or a fun family day trip, these seven offbeat towns to visit in Maryland will amaze and inspire.
St. Michaels
It’s for good reason that St. Michaels has been declared the "Heart and Soul of the Chesapeake Bay." Not only is this coastal town pretty, but it’s also rich in history. Any visit should include the 16-acre Chesapeake Bay Maritime Museum, an interesting attraction that has done an excellent job of preserving the coastal region’s history through its historic buildings, a working boatyard, and fascinating interactive exhibits. The iconic 1879 Hooper Strait Lighthouse is another must-visit at the museum.
Another must-visit is St. Michaels Winery where guests are often surprised to learn that Maryland makes some mighty fine wines through tours and tastings. You can explore vintages at WineFest St. Michaels in April, as well as catch some exotic car vibes at the Classic Motor Museum of St. Michaels’ annual car show.
Berlin
Savvy marketers have dubbed Berlin as "America's Coolest Small Town," and it's easy to see why. Situated just a short drive from Ocean City and Assateague Island National Seashore, Berlin's picturesque, people-friendly streets are lined with beautifully restored Victorian buildings, boutique shops, and gourmet restaurants. The offbeat Berlin Arts and Entertainment District is a must-do and showcases an array of local talent in its over 60 shops, galleries, and studios, with live music often scheduled.
The historic Atlantic Hotel, a centerpiece of the town since the late 19th century, is another walking tour highlight. Better still, book a night or two stay at this charming 3-star hotel and use it as a base during the quirky Berlin Fiddlers Convention which brings musicians and fans together for a weekend of live bluegrass and old-time music each September.
Chestertown
Chestertown is located on the banks of the Chester River on Maryland's Eastern Shore and makes for a lovely Maryland day trip or weekend getaway. With its origins dating back to the 18th century, Chestertown's well-preserved colonial architecture and cobblestone streets are just begging to be wandered and provide a unique glimpse into the America of old. If possible, time a visit to coincide with the Chestertown Tea Party Festival. Held each May, this family-friendly event commemorates the town's bold 1774 act of rebellion against British tea taxes, mirroring the more famous Boston Tea Party, with re-enactments, costumed parades, crafts, and boat races.
It's also a great time to explore the Chestertown Riverfront, a popular spot for walks and bike rides. The Chestertown Farmers Market, held here every Saturday year-round, is another great excuse to visit this fun little town.
Solomons
Located at the confluence of the Patuxent River and the Chesapeake Bay, the town of Solomons is another destination that’s known for its attractive waterfront. Highlights include the Calvert Marine Museum with its exhibits on paleontology, estuarine biology, and maritime history. There’s also a working boatyard where visitors can see traditional boat-building techniques and tour the early 1900s Drum Point Lighthouse, an iconic screw pile affair that offers a look at the life of those who manned these life-saving structures.
The Annmarie Sculpture Garden & Arts Center is another of the best attractions in Solomons. This attractive garden showcases a collection of sculptures on loan from the Smithsonian Institution and the National Gallery of Art set among walking paths, gardens, and natural woodlands.
Thurmont
Thurmont is a picturesque small town located in the foothills of the Catoctin Mountains, the easternmost section of the Blue Ridge Mountains. It’s a popular spot for nature lovers for its proximity to Cunningham Falls State Park, famous for its photo-worthy 78-foot cascading waterfall, the largest in Maryland. Recreational activities include hiking a variety of well-marked trails, including the popular Cunningham Falls Trail. Camping, fishing, and swimming are also enjoyable here.
Adjacent to Cunningham Falls, Catoctin Mountain Park is managed by the National Park Service and boasts miles of hiking trails, scenic vistas, and the chance to spot wildlife… and, if you’re extremely lucky, the occasional President as it’s also home to Camp David, the presidential retreat. For a little offbeat fun, visit during the annual Catoctin Colorfest in October, one of the largest outdoor craft shows on the East Coast.
Oxford
Named after the famed university town in England, Oxford was established in 1683 and is one of the oldest towns in Maryland. Top attractions include the Oxford-Bellevue Ferry, the nation's oldest privately operated ferry service which has been connecting Oxford with Bellevue across the Tred Avon River since 1683. This scenic ferry ride offers picturesque views of the surrounding waterways and is a unique way to experience the area's natural beauty.
In-town attractions include the Oxford Museum. Although small, it provides a fascinating glimpse into the town's rich history from its days as a bustling port and shipbuilding center to its current status as a peaceful waterfront community.
Havre de Grace
Named after the port city of Le Havre in France, Havre de Grace is strategically located where the Susquehanna River meets the Chesapeake Bay and is a picturesque waterfront town that appeals equally to nature lovers and history buffs. A standout attraction is the Concord Point Lighthouse, the oldest continuously operated lighthouse in Maryland. Built in 827, visitors can climb to the top for panoramic views of the bay and the river, as well as visit the keeper's house museum.
Those who enjoy quirky things to do will enjoy the Havre de Grace Decoy Museum, a unique attraction that celebrates the decoy carving tradition in the Chesapeake Bay region. The museum showcases an extensive collection of hand-carved decoys, demonstrating the artistry and craftsmanship that have cemented Havre de Grace’s reputation as the "Decoy Capital of the World."
The Final Word
Exploring these small towns in Maryland t presents a unique journey through the heart of one of the prettiest parts of the USA’s Mid-Atlantic region. From the maritime heritage of St. Michaels and Solomons to the historical richness of Chestertown and Oxford, each of these charming towns is worth exploring. Whether you’re here for a day, a weekend, or a week, these seven offbeat towns to visit in Maryland will inspire and amaze even the most seasoned of travelers.
