6 Fairy-Tale Small Towns In Delaware

Unusually shaped with a near-circle on top and a near-right angle at bottom, unusually situated as a tiny coastal sliver that can be leisurely crossed on foot, and unusually populated with fairytale-like characters, Delaware must appear as a veritable Oz to Mid-Atlanticers. In places like Lewes, Ashland, and Milton, tourists can see the Fountain of Youth, Enchanted Woods, Steampunk Treehouse, Sherwood Forest, and other fantastical locales. Learn where exactly to find them.

Ashland

Ashland is an unincorporated community in the Wilmington metro area. However, instead of being just another sprawling suburb, Ashland sprawls with greenery thanks to the 130-acre Ashland Nature Center, 471-acre Auburn Valley State Park, and 1,000-plus-acre Mt. Cuba Center. But the most magical preserve near Ashland is Winterthur. Sounding like a faraway land and looking the same, Winterthur comprises a museum and garden on 1,000 winsome acres. Winterthur's museum was originally home to the du Pont family and now displays around 90,000 classic American objects throughout 175 rooms.

Winterthur's garden spans 60 acres, three of which are called the Enchanted Woods. "Designed to look as though it were created by fairies," the forest has everything from a faerie cottage to an acorn tearoom to a mushroom spray park, plus it hosts the Enchanted Summer Day each June.

Milton

If you consider Paradise Lost a fairy tale, Milton, DE, honors one of the best fairy tale tellers. John Milton wrote that fantastical religious epic in the 17th century and, according to Dela-lore, lent his name to a small Delaware town two centuries later. Of course, he was long dead when Milton was named, and when Milton erected a statue of him in Mill Park. The John Milton Statue sits on a bench along a walkway and is seasonally dressed by anonymous townsfolk. For instance, he has donned a Santa hat for Christmas and a leprechaun beard for St. Patrick’s Day.

After seeing what Milton is wearing, check out an even stranger sculpture at the Dogfish Head Brewery. Jutting 40 feet from its lawn is Steampunk Treehouse, which looks like the home of futuristic fairy-bots. In truth, it was built from recycled and reclaimed materials for 2007's Burning Man and moved to the brewery in 2010. Although you can admire it from the outside, the inside is reserved for brewery staff.

Laurel

In the early 1900s, Laurel was the center of a sweet potato boom, so much so that it needed designated buildings to store all those spuds. Though blight wrecked the industry by mid-century, Laurel's Potato Houses sweetened the surrounding scenery and later the National Register of Historic Places. Few of them survive today, but you can go on a rustic journey for the remaining ones before seeing a remaining swath of normally faraway forest.

Outside Laurel sits Trap Pond State Park, which preserves the "northernmost naturally occurring stand of baldcypress in the US." Resembling thick swamps from southern states or fantasy realms, Trap Pond can be explored via canoe, kayak, pontoon, or a variety of annual activities during the Trap Pond Nature Festival held each April.

Lewes

Before Lewes was Lewes, it was a Dutch colony called Zwaanendael, meaning "Valley of the Swans." The Dutch were gone by 1632, but they are not forgotten thanks to the Zwaanendael Museum. Modeled after the old town hall in Hoorn, the Netherlands, the museum looks like a gingerbread house and harbors something that would scare Hansel and Gretel long before the witch did. Grimacing from behind glass is the Zwaanendael Merman, a mishmash of mummified/crafted animals meant to look real, ala the famous Fiji mermaid. The museum's other artifacts are mostly standard, but you can find more fantastical features in the vicinity.

They include the Lewes Town Clock, a 15-foot timekeeper fit for a storybook; the Fountain of Youth, a supposedly age-reversing spring marked by a gazebo-like structure; and Cape Henlopen State Park, a natural wonderland that hosts the Children’s Fantasy Trail, where kids trick-or-treat with their favorite storybook characters leading up to Halloween.

Townsend

Townsend is a small town surrounded by scenic preserves. To the south sits Blackbird State Forest, to the east sits the Blackbird Creek Reserve, and farther east sits the Cedar Swamp Wildlife Area. Straddling the last of those sanctuaries is the Delaware Renaissance Faire, AKA Delafaire. Held each year from October to November, Delafaire consists of three themed weekends. 2024's themes were "Halloweekend," "Fantasy Weekend," and "Heroes & Villains Weekend." Beyond thousands of costumed guests, Delafaire has had designated costumed characters like Max the Goat, Gus the Gnome, Vadim the Rose Peddler, and a wandering comedic bard named Thom Fuewellrey. See if they return for 2025's edition, which is scheduled for October 25 to 26, November 1 to 2, and November 8 to 9.

Arden

Unlike Townsenders, Ardenites do not have to pretend they are in a fairy tale. Arden, DE, was founded on fairytale-like principles via Henry George's Single-Tax movement and William Morris's Arts and Crafts movement. As such, Arden is a whimsical village of artsy people and homes on lush land that cannot be owned, only leased for 99 years at a time. Sure, Arden's principles are fantastical, but they are also successful, to such an extent that they survive not just in Arden but in neighboring Ardentown and Ardencroft.

Residents of "the Ardens" spend their days exploring woods like Sherwood Forest and attending "gilds" (Ardenspeak for "clubs") featuring everything from crafting to folk dancing to performing Shakespeare. Outsiders can visit specialty stores like the Oddporium and festivals like the Arden Fair before considering a permanent move. "You are welcome hither" is Arden's motto. Of course, subscription to the aforesaid principles is required.

Delaware already evokes a fairy tale realm, but its small towns are even harder to place in reality. Yet, as shown above, such towns are really real and really wonderful. Between Ashland and its Enchanted Woods, Milton and its Steampunk Treehouse, Laurel and its Trap Pond State Park, Lewes and its Fountain of Youth, Townsend and its Delafaire, and Arden and its Sherwood Forest, which First State fantasy-style feature will you see first?