8 Storybook Towns In Maryland

Butterfly trails, waterfront gardens, and sunset cruises might sound like scenes from a fairytale, but you may be surprised to learn that they can actually all be found in several small towns across Maryland. Prefer a tale centered around delicious food? Hand-crafted burgers, locally brewed beer, and southern-style seafood await you as well. No matter your interests, step into the role of the protagonist and explore these seven storybook towns, where adventure and discovery await.

Hancock

Hancock, one of the oldest settlements in western Maryland, will take travelers back in time with its landmarks dating back to the 18th century. Begin your visit at the Bowles House, a 1780s farmhouse that serves as the town’s visitor center, showcasing both local and canal history. After exploring the exhibits, step outside to experience the nearby C&O Canal firsthand. Dating back to 1828, the canal was once a vital route for transporting goods along the Potomac River. The river, with several boating ramps, is also a popular spot for launching boats or fishing. After an afternoon at the water, hungry visitors can step ashore and grab a bite at Potomac River Grill, a riverside restaurant serving handcrafted burgers.

North Beach

North Beach, a waterfront town along the Chesapeake Bay, is entirely walkable, offering a refreshing break for those looking to leave their car behind for the weekend. Travelers can explore the Chesapeake Bay’s fascinating ecosystem at Wetlands Overlook Park, home to a number of migratory fowl, a pier, and two gazebos where visitors can unwind and enjoy the views. Strolling along Bay Avenue, visitors also may come across the Mark R. Frazer Sunrise Garden, a cozy neighborhood park featuring shallow ponds, waterfalls, rain gardens, and native plant landscaping. Just a block from the coastline, enjoy a meal at Hook & Vine, a southern coastal restaurant known for its fresh seafood and good wine.

Leonardtown

As Southern Maryland's only Arts & Entertainment District, Leonardtown proudly displays its art through murals and art trails. The Butterfly Trail in downtown Leonardtown, for example, is lined by vibrant butterfly banners and flags created by local artist Eric Clark Jackson. Across from Leonardtown’s historic Square, visitors can also appreciate the Hurry Family Parkette Mural, which depicts Leonard’s wharf and downtown district. After appreciating the town’s local artists, drive out to the edge of town to the tasting room at the Port of Leonardtown Winery, home to the county’s first commercial winery, winning over 150 awards since its opening in 2010.

St. Mary's City

St. Mary’s City, founded in 1634, is one of Maryland's first European settlements, characterized by numerous museums, lighthouses historic churches, and war sites. Travelers can explore the St. John’s Site Museum, where they can view a 17th-century excavation site and several artifacts, and the Woodland Indian Hamlet, which provides an interactive look at the lifestyle of the Yaocomaco people. After exploring the town's historic sites, guests can visit nearby farmers markets, such as the California Farmers Market, The Home Grown Farmers Market, or the Barns at New Market, where they can enjoy locally produced goods and a charming, rural atmosphere.

Cumberland

Often referred to as “The Gateway to the West,” Cumberland is an artsy mountain town located in the state’s extreme northwest. About a half-hour drive from town, visitors can reach the remote Dan’s Mountain State Park, situated on a 16-mile-long mountain and home to an Olympic-sized swimming pool, four pavilions, and a serene fishing pond. The Thrasher Carriage Museum is another whimsical attraction, featuring an antique collection of horse-drawn wagons and sleighs. As a designated Arts & Entertainment district, make sure to catch a Cumberland Theatre production, a playgroup that has been performing since the late 1980s. The town also has rich McCoury music influence, which travelers can particularly appreciate during the annual DelFest, a family-friendly music festival that takes place along the Potomac River.

Berlin

Berlin has been rated time and time again as one of the top towns to visit, largely thanks to its expansive main street and arts district. Strolling along Berlin’s Main Street, visitors can explore over 60 shops and boutiques, some local favorites being Fathom & Co, a home accessories and gift shop, and Patty Jeans Boutique, a charming clothing boutique. Before visiting Berlin, travelers should be familiar with the Berlin Bubble Project. This project periodically hides hand-blown glass stars all throughout the historic downtown area, so keep your eye out! In addition to its impressive downtown, travelers can explore nearby natural attractions. Herring Creek Nature Park, less than a 15-minute drive away, features a five-acre nature trail, popular for bird watchers and picnickers.

Thurmont

Considered Maryland’s “Gateway to the Mountains,” there is no shortage of parks and trails to explore near Thurmont. Before starting a day of hiking, grab a savory sandwich at The Farmhouse Exchange, a cozy deli that uses locally sourced ingredients. Catoctin Mountain Park is one of the most popular outdoor attractions, with 25 miles of hiking trails, six miles of horse trails, and various historical exhibits such as the Blue Blazes Whiskey Still and Sawmill to explore. West of Thurmont, visitors can also spend a day at Cunningham Falls State Park, home to a 43-acre man-made lake and a 78-foot cascading waterfall. Also in the state park is the Catoctin Furnace, a stone furnace dating back to 1774 that provided ammunition during the American Revolution.

Chesapeake City

Chesapeake City is a bustling canal city characterized by its 19th-century architecture. Upon arriving in town, visitors can take a stroll along the Ben Cardin C&D Canal Trail, a scenic 17-mile trail that stretches from one end of the canal to the other, ending in the neighboring Delaware City. Also on Chesapeake City’s waterfront is Pell Gardens, a small park with brick-lined walking paths and a gazebo. There are plenty of ways to explore the bay, one of the most popular being a tour with Chesapeake Water Tours, which offers sunset cruises, sightseeing tours, and an iconic Rum & Reggae Cruise, among other functions. Bayhead Brewing Company is one of the most common places to unwind in town, offering over 10 on-tap beers in its rustic-style taproom.

Final Thoughts

As the year draws to a close, it is the perfect time to pause and truly appreciate your surroundings. Maryland is home to countless magical towns, all of which are just a short trip away. With so many incredible destinations at your fingertips, why stay at home? Choose a town that piques your interest, and let it inspire the next chapter of your journey.