6 Playfully Peculiar Towns In Delaware

Think Delaware is too mundane to be surprising? Think again. Nestled between Maryland, New Jersey, and the Atlantic Ocean, the First State may be flat and coastal, but the stories run deep. This was the first state to ratify the Constitution, and some of its towns date back to the 1600s. You can still find hidden old Dutch architecture, colonial battlegrounds, and Revolutionary War shipwrecks along the shore. But history is only half the story. These six little towns may be the weirdest: steampunk treehouses, ghost stories, desiccated mermaids, and candy sign fan bases. So pack your bags and visit six towns where odd landmarks and bizarre traditions are part of everyday life.

Rehoboth Beach

This coastal town mixes boardwalk kitsch with local quirks. Begin your journey at the Rehoboth Art League’s “Doors of Fame,” which has over 285 signatures of local artists and visitors inscribed on three antique wooden panels since the 1930s. After that, head to the Giant Dolle’s Salt Water Taffy Sign just outside the Rehoboth Beach Historical Society & Museum. The sign was removed in 2021, but public outcry led to its return. Many considered its removal an injustice, since Dolle’s isn’t just any candy brand, it holds the town’s collective memory.

For fresh air, stroll through Grove Park, where shaded paths and quiet benches feel miles away from the boardwalk. End your day at Café Azafrán. The café serves Mediterranean cuisine and hosts themed nights that match the funky vibe of the town.

New Castle

Your visit here comes with costumes, candlelight, and cannon fire. Start at the Amstel House, a Georgian mansion known for its haunted reputation and as the centerpiece of the annual Hauntings in History Tour. Candlelit rooms, ghost stories, and the mysterious “Woman in Blue” set the tone. Then walk up to the First State National Historical Park, where guides in 18th-century dress share real trial records, family feuds, and the darker corners of town history.

Next, stop by the New Castle Courthouse Museum, where Delaware voted for independence in 1776. If you’re visiting in June, catch Separation Day, a full-on colonial-themed festival with reenactments, artisan booths, fireworks, and live music.

Milton

Peculiarity has always been the norm in Milton. Your first stop should be the Steampunk Tree House, a metallic structure originally built for Burning Man by artist Kate Raudenbush. It now sits beside the old Dogfish Head campus, part sculpture, part fever dream. Next, explore Lavender Fields at Warrington Manor LLC. The air smells of herbs and bees as you browse homemade teas, soaps, and infused oils.

Visit during Milton Zombie Fest, a cheeky annual event where locals dress up, roam the streets, and raise money for good causes, all while staying proudly undead.

Smyrna

Every historic building in Smyrna has two tenants: the living and the dead. This town is said to be one of Delaware’s most haunted. Begin at the Smyrna History Museum, where exhibits highlight railroad heritage, firehouse artifacts, and civic curiosities that make the past feel close. Then, head to Historic Belmont Hall, where tours take you through the colonial-era mansion. Some locals swear they’ve heard ghostly footsteps echoing in the halls.

Stop by the Smyrna Opera House for bluegrass or community theater. End the day at Woodland Beach State Wildlife Management Area, where the marshlands grow silent at dusk and shadowy figures have been glimpsed, then vanished.

Fenwick Island

This barrier island looks quiet, but its curiosities are indefinite. Start your day with a beach stroll at Fenwick Island State Park, where soft dunes and gentle waves keep things peaceful. But the oddest stop is the DiscoverSea Shipwreck Museum. Alongside gold coins and lost cargo are eccentric finds: a dried merman and a walrus penis bone.Most visitors come for the shipwreck treasure, but it’s the dried merman that keeps them talking.

Get dinner at Our Harvest, where small plates and cocktails spotlight local produce. Then head to the Fenwick Island Lighthouse to end the day with a sunset view from Delaware’s southern tip.

Lewes

This small coastal town doesn’t hide its scars or its secrets. Begin at Cape Henlopen State Park, where abandoned World War II bunkers lie hidden in the dunes. Then head downtown to the Zwaanendael Museum, where Dutch-settler exhibits sit beside the grotesque Fiji merman floating behind glass.

Next, visit The Lewes Maritime Museum at the Cannonball House, still marked by British fire from the War of 1812. Finally, check out the Roosevelt Inlet Shipwreck site, where remains of a Revolutionary-era wreck have begun surfacing again just off the coast. It’s one of the few places where centuries-old wreckage still washes up between sunscreen and seashells. Waves still uncover timbers and artifacts, which keep this wreckage talk of the town.

Not Your Average Day Trip

You don’t have to go far to find something interesting. Delaware’s small towns show that strange and everyday often share the same zip code. These places don’t need to market their oddity. They live with it. A metal treehouse, a merman in a museum, a battlefield house with a cannonball still in the wall. There’s room for the bizarre, even in a small state like this. If you like ghost stories, unusual curiosities, or want to go somewhere that doesn’t feel like every other weekend drive, these towns won’t disappoint. Fill up the tank, hit the road, and don’t forget your camera. The stories are real. You just need to notice them.