5 of the Quirkiest Small Towns in the Mid-Atlantic Region

If you’re looking to get off the beaten path in the Mid-Atlantic region, small towns are often full of surprises. From destinations with haunted bridges and annual pony swims to those characterized by artsy streets and beloved local festivals, these five towns are places where history, creativity, and charm come together in the most delightful ways.

Berlin, Maryland

Berlin doesn’t try too hard to impress, and perhaps that’s exactly what makes it so charming. Just a few miles from the busy boardwalks of Ocean City, the laid-back town of around 5,000 people boasts colorful Victorian buildings and a walkable downtown that’s a joy to meander through. Berlin is also known for hosting quirky events such as the annual Bathtub Races, in which participants dressed in creative costumes race handmade tubs down Main Street, and the Fiddlers Convention, which fills the town with music, dancing, and friendly competition. 

Throughout the year, street festivals, farmers markets, and outdoor concerts keep the local community engaged and attract curious visitors from up and down the East Coast. Permanent fixtures include a range of indie boutiques, antique shops, cozy cafes, art galleries, and restaurants focused on farm-to-table fare, craft brews, and fresh seafood. 

Asbury Park, New Jersey

Part of the famous Jersey Shore, Asbury Park is a beach town known for its mile-long boardwalk, wide sandy beaches, and revitalized town center. Its revival is thanks in large part to the Asbury Park Music Foundation, which saw potential in the town after its popularity declined in the second half of the 20th century, leaving much of it in disarray. Today, Asbury Park is known for its vibrant live music scene, with performances happening nearly every night of the week at iconic venues like the Stone Pony, made famous by a young Bruce Springsteen at the start of his career. 

Another characteristic that sets Asbury Park apart from other coastal cities in New Jersey is its relationship with the paranormal. The town is widely considered to be haunted, with visitors reporting ghostly encounters in historic locations such as the Berkeley Oceanfront Hotel, Paramount Theatre, and Ashbury Lanes. Ghost tours run regularly, and if you can’t get enough of the eerie vibes, check out the Paranormal Museum, where an eclectic collection of strange artifacts and oddities are on display.

Woodstock, New York

Woodstock was once set to host a festival for the ages — the 1969 Woodstock Music & Art Fair, but local opposition and logistical obstacles ultimately pushed the event 60 miles down the road to Bethel. Still, the name stuck, thanks to Woodstock’s already-established reputation as a haven for artists, musicians, and free thinkers. Decades later, that creative spirit is still thriving, defining the town and setting it apart from its neighbors in the Catskills and Hudson Valley. 

The atmosphere in Woodstock is unmistakably bohemian, with colorful galleries, crystal shops, tarot readers, and indie bookstores lining Tinker Street, the town’s main drag. Cafes and green spaces regularly host live music on warm afternoons (including the drum circle on Sundays at the Village Green). And despite Woodstock’s famous reputation, the community remains grounded and innovative, curating an easygoing atmosphere that feels welcoming to visitors.

Chincoteague, Virginia

Chincoteague is part of Virginia’s barrier island system, located on the eastern shore of the state on the Delmarva Peninsula. It is the state’s only developed barrier island, but Chincoteague has another claim to fame: the Chincoteague Annual Pony Swim, an event made famous by Marguerite Henry’s 1947 novel Misty of Chincoteague. 

The swim takes place on the last Wednesday in July, drawing huge crowds to Chincoteague to watch the ponies make their way across the bay from neighboring Assateague Island. Once they arrive in Chincoteague, an auction is held, with proceeds supporting the Chincoteague Volunteer Fire Company, which helps care for the island’s herd of wild horses and funds this long-standing tradition. The weeklong Chincoteague Volunteer Firemen’s Carnival happens around the event and adds to the fun with rides, games, live entertainment, and plenty of classic fried fair food. 

New Hope, Pennsylvania

Known for its eclectic shops, vibrant arts scene, strong LGBTQ+ presence, and even the occasional haunting, New Hope is a town of about 2,600 people located 30 miles north of Philadelphia. Despite its proximity to the city, New Hope has an independent vibe, and the preserved 18th- and 19th-century buildings now used as shops and cafes give it an old-fashioned feel. Artisan boutiques sell everything from handcrafted goods to gothic art and vintage treasures, while art galleries and live music venues put the town’s creative spirit on full display. 

There are also rumors of ghosts of former townsfolk still lurking in the shadows of haunted locations like Crybaby Bridge and the Aaron Burr House, a bed-and-breakfast said to have harbored Burr after he shot and killed Alexander Hamilton in their famous duel. But even if you’re not a fan of the paranormal, New Hope’s walkable streets, riverside setting, and creative atmosphere make it one of the most appealing small towns on the East Coast.