6 Breathtaking Towns to Visit in Maryland

While not the smallest state in the USA - that title goes to Rhode Island - Maryland is certainly easy to get to. Sandwiched between Pennsylvania, West Virginia, Virginia, New Jersey, and Delaware, and butting up against Washington DC, the “Free State” is one of the best places to visit in the Mid-Atlantic region for those seeking an authentic Maryland travel experience.

And there’s no better way to get to know Maryland than by spending time in one or more of the state’s small towns. From picturesque waterfronts overlooking Chesapeake Bay to historic streets lined with centuries-old buildings, the best of these towns are perfect for travelers seeking somewhere special to visit. Whether for a few hours or a few days, check out these six breathtaking towns to visit in Maryland for ideas and inspiration.

St. Michaels

Its location on Chesapeake Bay’s Eastern Shore makes the quaint town of St. Michaels an ideal spot for a Maryland getaway. Popular for its rich maritime history and scenic beauty, St. Michaels has been dubbed "the town that fooled the British" for its pivotal role in the War of 1812 when residents hung lanterns in trees outside town, causing British cannons to overshoot their targets. More can be learned about this and other important historic events in the Chesapeake Bay Maritime Museum, set on 18 waterfront acres with interactive exhibits on the Bay’s history, culture, and ecology, as well as restored historic ships and a working boatyard.

St. Michaels Winery is another notable attraction and is part of the Chesapeake Wine Trail and features tastings and tours. Enjoy more active pursuits? Kayaking and sailing are popular things to do in St. Michaels, with several local companies offering rentals and guided cruises.

Berlin

Although much smaller than its namesake in Germany, Berlin, MA, boasts plenty of good excuses for a visit. Dubbed "America's Coolest Small Town" by savvy marketers, Berlin is situated just a few miles from Ocean City and some of the best Atlantic beaches, making it an ideal base from which to explore this breathtaking corner of Maryland. Visitors should start in Historic Downtown Berlin with its charming Victorian-era buildings housing art galleries, antique shops, and boutique stores. Main Street is also the scene of some of the town’s coolest events and festivals, including the Berlin Peach Festival (August), the Berlin Fiddlers Convention (September), and the Victorian Christmas celebration in December.

One of the most popular attractions in Berlin is the Calvin B. Taylor House Museum, a restored historic home dating to the 1830s that provides a glimpse into the life of a prominent local banker and the town's history. Nature lovers are also catered to with the nearby Assateague Island National Seashore being a must-visit. Famous for its wild ponies, the park offers stunning landscapes, pristine beaches, and opportunities for birdwatching, hiking, and biking.

Chestertown

Chestertown’s location on the banks of the Chester River is certainly breathtaking. Established in 1706, this quaint riverside town is steeped in colonial history and is home to Washington College, founded in 1782 one of the oldest colleges in the nation. Though its well-preserved buildings are not open to the public, the grounds can be explored. If possible, try to time a visit to coincide with the always fun Chestertown Tea Party Festival which commemorates the town’s defiance against British tea taxes in 1774 with re-enactments (yeah, tea-tossing!) a parade, and various other activities.

Historic Chestertown district is also fun to wander with its beautiful 18th-century homes and charming brick sidewalks (walking tours of the district are available). Interested in art? The RiverArts gallery is a must-visit and hosts exhibitions, workshops, and classes, while the Garfield Center for the Arts located in the historic Prince Theatre offers a regular roster of plays to concerts.

Oakland

Oakland is just minutes away from the state border with West Virginia and just a short drive from the popular Deep Creek Lake area, making it a prime destination for outdoor enthusiasts. For these folks, a visit to Swallow Falls State Park is a must-do. The star attraction here is Muddy Creek Falls, a 53-foot waterfall that’s especially breathtaking in the autumn when the foliage is in full display. Speaking of which, the town is known for its vibrant Autumn Glory Festival, a five-day celebration held for over 55 years each October that includes parades, craft shows, and musical performances.

In-town attractions worth visiting include the Garrett County Historical Museum with its local history exhibits showcasing the early days of the railroad, the impact of the coal industry, and artifacts from the Civil War.

Havre de Grace

Havre de Grace is located at the confluence of the Susquehanna River and Chesapeake Bay and boasts one of the state’s prettiest waterfronts. Standout attractions include the Concord Point Lighthouse, built in 1827 and the oldest continuously operated lighthouse in Maryland. It marks the entrance to the Susquehanna River and provides stunning views of the bay. The keeper's house, which serves as a museum, is also worth popping into.

Another pretty spot is the Promenade, a scenic boardwalk that runs along the shoreline with great water views and easy access to Tydings Park, a popular picnic spot. Enjoy quirky attractions? The Havre de Grace Decoy Museum celebrates the local tradition of waterfowl hunting and decoy carving, an art form that the area is known for, and features an extensive collection of handcrafted decoys. The Havre de Grace Maritime Museum provides a comprehensive look at the town’s maritime history, including its role during the War of 1812 and the Chesapeake Bay area’s development.

Thurmont

Its location just off the I-70 south of the Pennsylvania border makes Thurmont a great day trip destination (it’s just 90 minutes away from Baltimore). Adding to its allure is its proximity to the Catoctin Mountains and Cunningham Falls State Park, which boasts Maryland's highest cascading waterfall. The park offers a range of outdoor activities, including hiking, camping, and fishing, with trails leading to the picturesque 78-foot waterfall and Hunting Creek Lake. It, too, is especially nice in the fall.

Catoctin Mountain Park, managed by the National Park Service, is another picturesque spot. Here visitors can explore miles of hiking trails, partake in ranger-led programs, and visit scenic overlooks for breathtaking panoramic views of the Monocacy Valley. The park is also home to Camp David, the presidential retreat, adding a unique historical dimension to its appeal.

The Final Word

However they get there and however long they stay, travelers won’t be disappointed with a trip to any (or all!) of these six breathtaking towns in Maryland. From the maritime heritage of charming St. Michaels and the artistic vibrancy of Berlin to the rich history of Chestertown and the natural beauty of Oakland - not to forget Havre de Grace’s pretty waterfront and Thurmont’s spectacular scenery - these towns offer a glimpse into the very heart and soul of this pretty part of the United States.