
10 Quirkiest Delaware Towns To Visit In 2025
Delaware may be small, but it’s packed with weird, wonderful towns that surprise visitors in the best ways. These aren’t your average travel spots. Instead of packed beaches or big-name museums, you’ll find towns with cozy restaurants, peach festivals, nature parks, and backyard steampunk sculptures. Some were built around shipyards or general stores. Others still have buildings from the 1800s standing strong.
From Christmas parades to political hatchet-burying ceremonies in Georgetown, Delaware has its own quirky brand. Each town has a story, a strange fact, or a local legend that makes it stand out. You might hear an urban legend from a café owner or come across a festival that feels more like a neighborhood block party. If you’re planning a 2025 road trip through Delaware, these towns are worth the detour and a second look.
Middletown

Middletown sits about 25 miles south of Wilmington and got its name because it marked the halfway point on an old cart route between Appoquinimink River and Bohemia Landing. In the 1600s, ox carts carried goods across this inland shortcut between the Atlantic Ocean and Chesapeake Bay. The crossroads eventually became home to Witherspoon’s Tavern (now known as Sully's Irish Pub at The Witherspoon), built in 1762. Today, you can visit Charles E. Price Memorial Park, catch a show at the Westown Movies, or grab donuts at Sweet Melissa Bakery & Coffee Shop. At Cochran Square, a memorial honors those lost in war, beginning with World War I.
Smyrna

Smyrna may seem quiet at first, but this town loves its quirks. Once called Duck Creek Cross Roads, Smyrna was a busy shipping port long before it got its current name in 1806. Shipbuilding, grain, lumber, and peach shipping made it an early economic hub. Two roads met at what’s now Main and Commerce Streets, once known as the “Four Corners.”
Some say the town name came from a powerful sermon preached by Francis Asbury, based on the biblical city of Smyrna. Today, Smyrna still keeps things interesting. Locals swap urban legends and ghost stories about the nearby Blackbird State Forest. Visitors can also check out The Lindens, a pre-revolutionary house that was saved from demolition. Hungry after a stroll? Don’t forget to check out Brick Works Brewing and Eats for pub grub and house beers.
Georgetown

Georgetown was built on purpose. In 1791, Sussex County residents wanted a town closer to the center of the county, so they made it happen. Commissioners bought farmland, laid out streets, and named the new place after George Mitchell, one of the men behind the plan. At the center is The Circle, where the 1839 courthouse still stands.
Every two years, Georgetown hosts Return Day, a quirky tradition where election results are read aloud and political rivals bury a hatchet in the sand to symbolize peace. You can tour antique carriages and a working telephone booth at the Marvel Carriage Museum, browse jams and home goods at the Red Barn Country Store & Farm, or check out restored warbirds at the Delaware Aviation Museum Foundation.
Clayton

Clayton was first incorporated in 1887 with five commissioners tasked with organizing elections, collecting taxes, and managing street layouts. By 1897, it had a full town council, annual tax caps, and even rules about dog ownership fees. Today, Clayton still keeps that independent spirit, but it’s also full of small-town surprises. Take a ride on restored engines at the Clayton Railroad Museum or explore the nearby Blackiston Wildlife Area, home to wetlands, wildflowers, and quiet birdwatching spots. For a solid meal, grab lunch or dinner at Jack’s on Main, a cozy restaurant known for comfort food done right.
Millsboro

Millsboro might look like a quiet farming town, but its history and quirks run deep. It started at a narrow spot in the Indian River, where Elisha Dickerson built a dam and grist mill in 1792. The area had already been home to Native people, including the Assateague and Nanticoke, and remnants of their communities still shape the region.
You can learn more about their history at the Nanticoke Indian Museum, one of the only tribal museums in the state. Today, Millsboro mixes history with fun. Night kayaking at the nearby Trap Pond State Park lets you rent boats to float under the stars. Play golf at the Plantation Lakes Golf & Country Club or head to Cupola Park for a picnic.
Laurel

Founded in 1683 and incorporated in 1883, Laurel was once one of Delaware’s wealthiest communities, with 2,500 residents, 11 general stores, and even a carriage factory. A massive fire in 1899 burned down part of Market Street, leading to the creation of the Laurel Volunteer Fire Department.
Laurel has also produced five Delaware governors and now holds more historic buildings than any other town in the state, with over 800 listed on the National Register of Historic Places. Stop by Abbott's on Broad Creek for their popular French onion soup or crispy calamari, or hang out at Roger C. Fisher Laurel River Park. Buy your souvenirs from This-N-That Country Store before roller-skating at Skateworld. With about 4,000 people, Laurel stays small but full of stories.
Townsend

Townsend is a small farming town that covers 384 acres. It sits along the Appoquinimink River and Wiggins Mill Pond, near communities like Blackbird and Alisa Estates. Incorporated in 1885, Townsend still holds onto its agricultural roots. The town has 216 historic buildings and five listed structures, including the 1851 Lattamus Store, Winfield Cottage, and Harmon’s Drug Store from 1893.
Visitors often visit the 3 Palms Zoo & Education Center, a quiet spot surrounded by empty grasslands. The nearby Blackbird State Forest is an ideal stop for visitors wanting to hike, bike, or try horseback riding. For a cheese break, try the cheesesteaks and pizzas at Little Italy Pizza.
Elsmere

Elsmere began in 1886 when Joshua Heald bought farmland and built homes, creating what many call the first suburb in northern Delaware. With railroad lines and later trolley tracks running nearby, workers could easily travel into Wilmington for jobs. Elsmere became an official town in 1909, and traces of its early street layout still appear in the triangle parks and oddly angled intersections.
Nature lovers head to the nearby Ashland Nature Center or the Russell W. Peterson Wildlife Refuge, each offering quiet spots to hike, birdwatch, or picnic. Elsmere's annual Christmas Parade draws big local crowds, but smaller delights like Casapulla’s Subs, which has been serving Italian sandwiches since the 1950s, add to its small-town fun.
Milton

Milton sits on the Broadkill River and still carries the charm of its shipbuilding days, with preserved Victorian homes and a downtown area that feels like it’s been plucked from another era. Its annual festivals celebrate everything from local wildlife to river culture, drawing curious crowds looking for a different kind of getaway.
One of the town's oddest treasures is the Steampunk Tree House, a towering 40-foot metal sculpture that looks like it was built by time-traveling inventors and now sits proudly on the lawn of Dogfish Head Brewery. Grab a beer flight inside and peek at the offbeat décor. Nearby, you can hike through the Edward H. McCabe Preserve or paddle the Broadkill River, but make time for the Broadkill Banjos gathering, where locals bring their instruments and play riverside tunes late into the evening.
Ocean View

Ocean View may sit quietly near Bethany Beach, but it has more personality than its name suggests. Originally called Hall’s Store, the town grew around a single general store and eventually became a laid-back coastal community with more than a few oddball surprises.
The James Farm Ecological Preserve is a peaceful place for hiking and birdwatching. Bonkey’s Ice Cream & Snoballs offers unexpected flavors, and the art gallery at Ellen Rice Studio carries prints inspired by everything from dreams to Delaware’s ghost stories. And for something both quirky and real, check out the Tunnell-West House, a Gothic Revival-style home dating to the early 1900s, now being adapted as a museum by the local historical society. Its well-preserved, antique door hardware and interior trim tell a story all their own.
A Quirky Trip To Delaware
Delaware’s quirkiest towns are full of details you don’t find on maps. From Bonkey’s Ice Cream & Snoballs in Ocean View to the old trolley routes in Elsmere, these places reward curiosity. Some towns tell their story through architecture, like the 216 historic buildings in Townsend. Others use festivals, like Georgetown’s Return Day and Milton’s Banjos gathering. These towns may be small, but the memories they make are anything but.