10 Quirkiest Maryland Towns To Visit In 2025

Maryland may be small, but it is certainly big on personality, especially when visiting its quirky little towns. Beyond the famous urban sprawl of Baltimore and Annapolis lies a collection of offbeat communities where weird creativity thrives, traditions feel unusual, and every corner tells a story you won’t find in a guidebook. For any first-timer, these odd gems deliver a novel experience that leaves a lasting impression.

From the wild horses roaming the sandy shores of Berlin to the bizarre system of hidden caverns in Boonsboro, these destinations go against the grain with their twisted idea of entertainment, delivering something truly unexpected. If you want to add a dash of eccentricity to your 2025 travel plans, here are some of the quirkiest Maryland towns to visit.

Laurel

This vibrant town near Washington, DC, and Baltimore, along the banks of the Patuxent River, excites visitors with its motherlode of dinosaur fossils and house of horrors. Laurel lures budding paleontologists with a promise of witnessing prehistoric treasures at the Dinosaur Park. The site preserves a world-class collection of fossils dating back over 100 million years, providing a unique perspective of prehistoric life. Laurel's House of Horror thrusts guests into the world of spooky spirits, haunted horrors, and scared screams in an abandoned movie theater.

Meanwhile, the Dutch Country Farmer's Market provides a taste of Amish life in Maryland, where tourists can shop for baked goods, fresh farm produce, and Amish-style delicacies in a fun setting. Also, you take a trip down memory lane at the Montpelier House Museum, an 18th-century Georgian mansion that George Washington once visited.

Berlin

About 10 miles from Ocean City, this landmark town in Worcester County promises visitors a rare experience with wild horses and a quirky museum tour dedicated to a mythical creature. Berlin's vibrant Main Street harbors a cluster of attractions, from historical and culinary to entertainment. However, the strangest of all is the Mermaid Museum. This remarkable venue in the heart of downtown displays a library of artifacts, memorabilia, toys, and other paraphernalia exclusively related to mermaids.

Berlin is also famous for its unassumingly beautiful Assateague State Park. It's two miles of beach offers adventures like beachcombing, surfing, swimming, fishing, and sunbathing. Kayaking and canoeing are also popular for venturing into little coves or watching wildlife.

Boonsboro

This charming village in the foothills of South Mountain is known for its enduring historical heritage and picturesque natural scenery. Boonsboro is home to Crystal Grottoes Caverns, a spectacular network of underground caves with brilliantly lit chambers that transport tourists into a fantasy-like world. Inside lie awe-inspiring limestone formations believed to have formed millions of years ago. A visit to the Boonsborough Museum of History exposes the town's rich heritage, with interactive archives chronicling its role in the Civil War.

Meanwhile, Boonsboro beckons adventurers with fun activities at Greenbrier State Park. Straddling the shores of a 42-acre reservoir, the reserve offers canoeing, swimming, boating, and camping opportunities. Hikers can also access the famous Appalachian Trail, which is lined with sweeping vantage points along the way.

Crisfield

Christened "Seafood Capital of the World," Crisfield takes its moniker to heart by hosting one of the most unique festivals in the state. As the rest of the country celebrates Labor Day weekend, the town holds its annual National Hard Crab Derby. This eccentric festival features crab-themed events to entertain attendees, including crab-picking contests, costumed parades, vendors, and a crab race in honor of Maryland's famous blue crab.

But if you don't attend the festival, you can indulge in Crisfield's delicious crab cuisine at the Crab Place. The town's picturesque setting along the Chesapeake Bay opens doors for a delightful sail on the water, courtesy of Tangier Island Cruises. This easygoing cruise takes guests on a sightseeing adventure to the nearby islands.

Sharpsburg

This sleepy town in Washington County, steeped in American war heritage, allows tourists to relive the bloody events of the Civil War in Maryland. Sharpsburg was the site of the Antietam Battle, which is preserved at the Antietam National Battlefield. Almost 23,000 soldiers died or suffered injury from only twelve hours of nonstop, savage combat. The iconic Killiansburg Cave served as a temporary hideout for soldiers trying to survive the battle, and provides a surreal feel of the fear they must have been in, with a thin line to separate life from death.

While in the area, you can pay tribute to the lost lives at the Antietam National Cemetery, where over 4,700 Union soldiers were buried. Several guests have reported haunting experiences and paranormal activity on the site, which attracts many enthusiasts.

Crownsville

This unassuming village in Anne Arundel County is famous for taking visitors on an exciting journey through time to the 16th century. This happens annually during the Maryland Renaissance Festival, a unique festival that recreates a fictional 1500s English village, Revel Grove. The event plays out on a 27-acre property and incorporates whimsical costumes, witty stage shows, and offbeat cuisine.

Crownsville also invites golfers of all skill levels to gauge their proficiency at the Preserve at Eisenhower. An active bar scene brings the low-key downtown to life after hours, offering a great escape to link up with friends. This includes Lures Bar and Grille, where you can enjoy refreshing pints of craft beer while listening to local bands.

Cambridge

Cambridge is a beautiful town on the Choptank River, steeped in history and harboring landmark sites that bring its fascinating backstory back to life. The community was founded in the late 17th century and played a significant role during the Underground Railroad era. Historians visit the rustic Bucktown Village Store, believed to be Harriet Tubman's first stand in a show of defiance. Meanwhile, the Spocott Windmill and Village transport tourists back to the 19th century, with a chance to witness a period windmill still in operation.

Meanwhile, the Richardson Maritime Museum preserves over three centuries of maritime heritage in the region by displaying a library of archives and memorabilia. This is further emphasized by the Choptank River Lighthouse, which features a unique screw pile design.

Darlington

This diminutive village of Harford County earns its place among the quirkiest Maryland towns to visit in 2025 for its unorthodox Dreamscape Festival. Every June, attendees from within and without descend upon the city to mark this peculiar EDM music festival. Participants engage in three days of continuous upbeat music while dressed in expressive costumes in a dream-like environment with colorful decorations. It also involves a variety of shenanigans that allow you to unleash your inner child.

Darlington's well-preserved historic district is also listed on the National Register. The neighborhood houses several landmark buildings offering a blast from the past, including the Hosanna School Museum from 1867. Also, tourists can escape the outdoors at Conowingo Fisherman's Park, where terrific views of the Susquehanna River await.

Westminster

Westminster fully embraces its paranormal side by welcoming visitors to explore its multiple haunted sites. One of its most haunted venues is the Old Opera House along Main Street, which is believed to house the angry spirit of Marshal Buell, who was killed by the audience after poking fun at President Grant. Although not haunted, Hackney Haunts exposes visitors to spooky experiences guaranteed to get their adrenaline pumping. It entertains with a remarkable adventure through eerie hallways with scary figures and actors looking to give a classic scare.

When you need a break from the frightening occasions, you can escape to the tranquil setting of the Westminster Community Pond. This lovely oasis has grassy picnic spots overlooking a calm pond with swimming ducks.

Easton

Colorful culture collides with a booming art scene in the charming towns on Maryland's Eastern Shore. However, Easton turns heads with its annual Waterfowl Festival. This yearly extravaganza pays tribute to the region's heritage, focusing on nature, art, and wildlife. Approximately 20,000 people grace the festival, demonstrating alarming enthusiasm in celebrating ducks. The Academy Art Museum is the cultural hub in Easton, connecting audiences with the arts through workshops, classes, and world-class exhibitions throughout the year.

Easton also invites newcomers to experience authentic Amish life at the Amish Country Farmer's Market. This exciting market presents some of the best Amish creations and delicacies, including handcrafted furniture, pretzels, candies, and more.

Maryland’s small towns brim with quirky charm, from haunted streets and crab derbies to literary landmarks and funky festivals. Each offers a unique slice of history, humor, or oddball culture that sets it apart from the ordinary in the United States. Whether you are chasing ghosts in Westminster or reliving the Civil War's bloodiest battle in Sharpsburg, these peculiar Maryland towns to visit in 2025 promise something unexpected to discover. Exploring them is a reminder that the state’s most memorable moments often come from its quirkiest corners.