8 Of The Most Captivating Small Towns In Delaware

An oddly shaped state that can be leisurely crossed on foot and where corporations outnumber people, Delaware defines captivating. However, the second-smallest state's smallest communities are extra alluring, attracting tourists with a cannonball house, shipwreck museum, colonial tavern, flying saucer house, African American cemetery, temperance fountain, island fortress, and everything in between. Learn where to find these attractions and make them the first places you visit in the First State.

Lewes

As the first European settlement in Delaware, Lewes is a hub of historic sites. At its center is the Lewes Historic District, whose highlights are the Ryves Holt House, which is Delaware's oldest surviving residence as well as a museum and mercantile, and the Lewes Maritime Museum at the Cannonball House, which showcases a historic home and the British cannonball that smashed its foundation during the War of 1812. On the district's perimeter sits the Zwaanendael Museum ("Zwaanendael," meaning "Swan Valley" in archaic Dutch, was Lewes's first European name), a Dutch-style building with oddities like the trick-taxidermied Zwaanendael Merman. What captivating collections for a "city" of about 3,300 people.

Fenwick Island

If you think there can't possibly be TWO "mermen" in Delaware, discover the DiscoverSea Shipwreck Museum on Fenwick Island. Among its maritime artifacts, including thousands of items recovered from shipwrecks, is an alleged half-fish, half-humanoid creature. In truth, it was likely built from animal parts or else simply sculpted to look like a cryptid. If the merman and shipwrecks aren't sufficiently captivating, Fenwick Island, as the southernmost settlement in coastal Delaware, also offers the Seaside Country Store, a retailer of everything from cheese to shells dubbed the "most unusual store on the shore," and Fenwick Island State Park, a 350ish-acre preserve of real, living creatures like fish, crabs, and shorebirds.

New Castle

Another ancient community by Delaware standards, New Castle, has so many 17th- and 18th-century buildings that its central section is called Old New Castle. A tour of this several-block district takes you to the New Castle Court House Museum, which was built in 1732 as Delaware's first court house; the Amstel House, which was laid in the early 1700s for Irish physician John Finney; and the Dutch House, which dates to the late 17th century or turn of the 18th century and is considered the oldest building in town. Some New Castle haunts seamlessly combine history with commerce, such as Jessop's Tavern, whose colonial function was housing the namesake barrel maker and whose present function is serving beer, wine, and food with with Old Country influences. Drink Belgian beer and eat Dutch pot roast while contemplating Abraham Jessop's pre-American exploits.

Milton

Ever heard of a steampunk treehouse? No? Would you like to see a steampunk treehouse? If you answered "yes," your only option is to visit Milton, DE. This 3,300ish-person town boasts the 40-foot-tall Steampunk Treehouse. It was built out of recycled materials for 2007's Burning Man and now guards the grounds of the Dogfish Head Milton Brewery. Guests can admire it only from outside, however, as inside is reserved for staff.

Milton is one of two Delaware towns (the other is Houston) that preserves a "flying saucer house," the Futuro House. This out-of-this-world residence was designed by a Finnish architect and launched in several countries in the 1960s. Milton's Futuro House landed, appropriately, at the Eagle Crest Aerodrome.

Laurel

Sequestered in Delaware's southwest corner, Laurel is a gateway to gorgeous scenery. Trap Pond State Park sits just below town and provides around 3,800 acres of explorable wilderness. Parkgoers can camp luxuriously or primitively, hike many miles of trails, paddle the titular pond, watch for birds like woodpeckers and bald eagles, and marvel at the northernmost, naturally occurring stand of bald cypress trees. Also standing near Laurel are Potato Houses, relics of a spud-tacular time when Delaware was a sweet tater mecca. As such, these early-20th-century storage shacks are listed on the National Register of Historic Places. After glimpsing potato ghosts, you can eat fresh potatoes in Laurel proper at Britt's Dutch Inn and Abbott's on Broad Creek.

Delaware City

Like New Castle, Delaware City is a historic coastal community just south of Wilmington. It has only about 1,900 residents but multiple fortresses from more contentious—and captivating—eras. Fort DuPont State Park preserves buildings and gun batteries dating to the turn of the 20th century, while Fort Delaware State Park is a Civil War relic mixed with a lively heronry. The latter park is on Pea Patch Island and thus accessible by ferry. A more grounded Delaware City site is the Friends of the African Union Church Cemetery, which contains the graves of black Union soldiers who fought in the Civil War.

Rehoboth Beach

Few towns, if any, have transformed like Rehoboth Beach. Founded as a Christian temperance colony in the late 19th century, Rehoboth has grown and changed over the years. Among its lively attractions are Diego's Bar & Nightclub, Zelky's Beach Arcade, the Purple Parrot Grill, the Rehoboth Ale House, Jungle Jim's, Freddie's Beach Bar, Zogg's Raw Bar & Grill, and Funland, many of which line a mile-long oceanside boardwalk. Each day, thousands of boardwalkers pass the Woman's Christian Temperance Union Fountain, a water source built to deter boozing in 1929 and is now more ironic than inspirational.

Arden

While Rehoboth is captivating, thanks to change, Arden is captivating, thanks to resistance to change. This village was founded and continues to operate on turn-of-the-century communalist principles. Thus, land in Arden cannot be privately owned. Instead, it is leased for 99 years at a time. Homes on Arden land are owned, however, and since communalism developed alongside anti-industrial and Arts and Crafts movements, they are quaint and quirky. The Arden Craft Shop Museum is a former residence that displays Ardenfacts, while the Arden Gild Hall is a former barn that hosts performance art. Creative communalism culminates in the Arden Fair each summer.

A rare utopian community that worked, Arden birthed additional villages with the same principles: Ardentown in 1922 and Ardencroft in 1950. Combined, the Ardens have close to 1,000 residents.

An oddity of American states, Delaware's small size is counterbalanced by huge attractions. Its tiniest towns captivate with everything from nature preserves to historic forts to boardwalk bars to potato houses to communalist craft venues. During your next Delaware vacation, visit Lewes, Fenwick Island, New Castle, Milton, Laurel, Delaware City, Rehoboth Beach, and Arden for as many diverse, spectacular sites as you can find in a short section of America.