9 Quirkiest Maryland Towns You Didn't Know Existed
The Old Line State, Maryland, is full of strange experiences that border on surreal. These experiences are grounded by beaches and the Chesapeake Bay, which flows through the state like an artery, providing nourishment to the community. All together, the state is the perfect blend of quirky and cozy, giving all who wander endless opportunities for discovery. While the towns on this list are relatively unknown, they have so much to offer. Keep reading to plan a road trip full of blue crab feasts, ghost stories, and small-town folklore.
Boonsboro
Being frequently visited by a romance novelist (Nora Roberts) is only one of the things that makes this town so unique. The author even owns Boonsboro’s appropriately romantic inn, Inn BoonsBoro. The rooms are named after famous literary couples and have retained their historic design. Dive deeper into history at the only commercialized cave in Maryland. Crystal Grottoes Caverns has more formations per square foot than any known cave in the world. In only 40 minutes, explorers will find stalactites and stalagmites within the colorful caverns. For even more excitement and color, take a Gem Mill tour at the cave. This experience feels like it is straight out of a novel, where guests are invited to uncover fossils and gemstones hidden within the sand.
Jump into an actual novel at Turn the Page Bookstore. The books are housed within a pre-Civil War townhouse and are another connection to Nora Roberts, whose husband owns the shop. The shop is full of books, espresso, and quirky gifts. Roberts herself is at the shop three nights a week for book signings.
Grantsville
Grantsville feels otherworldly, being full of fantastical nature and artistic spirit. Travelers can see this where the natural world merges with human artistic craftsmanship at Spruce Forest Artisan Village. This village is a collection of 1800s-style cabins, each full of artists practicing their crafts. The artists showcase and sell their artwork, while also welcoming village visitors into their studio-cabin to talk about their process. Take the creative inspiration gained at these cabins to a stone bridge built in 1813. The Casselman River Bridge is a great opportunity for photographers, with the ancient stone arching over the Casselman River, which is surrounded by lush greenery.
For an abundance of nostalgia and sugar, head to Hill Top Fruit Market. This old-school candy store has over 900 varieties of candy available. There’s no need to pick just one type of candy, as the store allows customers to create their own Pick-A-Mix bags, which can be filled with their choice of sweets.
Berlin
Voted "America’s Coolest Small Town," this town lives up to its title. It was even the filming location for Runaway Bride and Tuck Everlasting. From one fantasy to another, discover mermaid lore and more at The Mermaid Museum, only nine miles from the sea. Full of art installations and colorful exhibits, this space makes for the perfect whimsical photo opportunity.
If the aquatic-themed museum leaves you thirsty, check out Burley Oak Brewing Company. Local art surrounds guests, who also get to enjoy live music and a wide variety of beer and cocktails. For just as much deliciousness with a stranger vibe, head to The Globe to have a meal or a drink in a century-old theater. The Globe holds open mic nights, hosts performances, and even community dance events.
Crisfield
Crisfield is known as the "Crab Capital of the World," but it has so much more to offer. To get a feel of local life, walk along Somers Cove Marina. With nearby shops and restaurants, the Marina is the central hub for aquatic tourism. Annual summer events bring tourists who love celebrating with famous blue crab feasts and other local fare. Travelers looking for whimsy can find it at “BIG Little Town Fest”, where Maryland's famous giant inflated duck passes the docs. From this Marina, take a cruise with Smith Island Cruises. The boat's voyage to a remote island makes a fantastic day trip, whether you want to relax on the sand or walk along the shore.
Return to the mainland and explore a different type of aquatic nature: salt marshes. Janes Island State Park has this in abundance, as well as 30 miles of water trails that lead to quiet beaches. This park is wild, creating an atmosphere that feels lost to time anywhere else in the world.
Takoma Park
Takoma Park is home to a treasure trove of instruments known as the House of Musical Traditions. The instruments here are varied, not only in origin but also in type. Electrical and traditional guitars, pianos, and more line the shelves alongside books on music and the culture they inspire. To continue to feel this small town's creative pulse, visit the shop that a local mom opened to make sure everyone finds the book that is meant for them. To achieve this goal, People’s Book has many books and zines that cater to unique tastes. The space also hosts speaker events and storytimes, making this a great choice for travelers with children. On weekends, head to the farmers' market for fresh goods from nearby gardens. While there, visit Roscoe the Rooster, a bronze statue made to commemorate a beloved local rooster that hung out in Takoma Park’s shops and businesses.
Lonaconing
Lonaconing is home to one of the last intact silk mills in the U.S. While the mill was shut down in the 1950s, it remains perfectly preserved. Lonaconing Silk Mill is open by appointment, and is an especially popular spot for photographers who want to take the rare opportunity to capture the beautiful historic machinery. The town’s other historic landmark, Iron Furnace Park, offers another rare glimpse into the past. The furnace that used to create 75 tons of iron per week now stands beside a playground and picnic area, welcoming history enthusiasts to witness this rare preserved piece of the past. To really appreciate this small town, see it from atop a mountain at Dan's Mountain State Park. This 481-acre park has spectacular views as well as ponds, pools, playgrounds, and pathways.
Leonardtown
Southern Maryland’s only designated art district is full of colorful murals on the sides of brick coffee shops and sculptures erupting from sidewalks. The town is also steeped in spooky lore, such as the legend of Moll Dyer. Moll was a suspected witch whom the townsfolk blamed for bad weather and damaged crops. She was eventually chased from her home in the middle of the night and left to freeze to death in the wilderness atop a rock. This rock remains in Leonardtown and is said to bear her handprint.
More wonder (without the side of spooky) awaits at North End Gallery. Housing both 2D and 3D art, the gallery is a sanctuary for artists of all types, and occasionally offers classes ranging from mosaics to pastels, and more. Nearby, the SOCIAL Coffeehouse and Cocktail Bar stands tall near Leonardtown Square, welcoming the wary with whimsy. The baristas and bartenders love to experiment, bringing new flavors and combinations to the menu. With leather couches inside and blazing firepits outside, it is easy to be comfortable for drinks or a delicious brunch in this popular local gathering spot.
Chestertown
A town with a rebellious spirit honors its past through the Chestertown Tea Party Festival. In 1774, townspeople met and set forth their resolves to forbid importing, selling, or consuming tea in response to British Parliament’s closing of the port of Boston. Now, hundreds of years later, townsfolk gather with a big block party and a reenactment of the “Chestertown Tea Party”. Behold another part of history as it sails along the Chesapeake. The Schooner Sultana is a replica of a 1767 merchant vessel commissioned by the British Navy. Seeing this ship set sail feels like stepping back in time and makes for a very rare experience.
The Schooner is special not only because of its exterior but also because it has original logbooks, crew lists, correspondence, and design drawings. Finally, taste locally loved freshly baked bread at Evergrain Bread Company. The bakery's focus is on retro-innovation, which combines the best baking practices of the past with the technology of the present. Along with homemade loaves, guests can also find flavorful pastries and coffee.
St. Michaels
The cozy town of St. Michaels contains many hidden gems as well as popular institutions such as the Chesapeake Bay Maritime Museum. The museum pays homage to its titular river while preserving the history and culture of the entire Chesapeake region. Luxuriate in the serenity created by the river at Inn at Perry Cabin. While adored for being a quiet and lavish getaway, this Inn is also known for the famous film The Wedding Crashers.
The film’s reception scene was filmed at the inn, where the pointe overlooks the river. After admiring it and learning about its history, travelers can take to the bay on one of the many themed cruises that depart from St. Michaels. Sail Selina cruises range from moonlight cruises to wine tasting and champagne sunset sails.
Finishing Thoughts
Maryland’s heart is comprised of salt water that soothes the spirit and adventures that re-wild the mind. The state is bursting with quirky adventures ranging from moonlit cruises to hiking through remote islands made of salt marshes. Whether you want to hunt for gemstones throughout cave systems or touch phantom fingerprints left on boulders, every type of tourist will find something to explore that is as fun as it is fascinating. The Seventh State meets visitors' curiosity with creativity, reminding visitors why this little state leaves a big impression.
