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Boardwalk at Rehoboth Beach in Delaware. Editorial credit: Ritu Manoj Jethani / Shutterstock.com

7 Most Eccentric Towns in Delaware

There are so many flavors to choose from when picking a destination. So, what do you look for when making plans? Eccentricity is a delightful ingredient in Delaware if you find yourself around the Mid-Atlantic and South-Atlantic states. Before The First State was settled by Europeans, the land was inhabited by the Eastern Algonquian tribes known as the Unami Lenape. Today, thanks to the ocean moderating its climate, the Blue Hen State is a great place to visit Rehoboth Beach, explore the Winterthur Museum Garden & Library, and tour the Nemours Estate. If you were looking for the unexpected or just wanted a new, interesting flavor in life, Delaware has all that and more.

Lewes

Downtown Lewes, Delaware.
Downtown Lewes, Delaware. Image credit: Harrison Keely via Wikimedia Commons.

Eccentricity often translates to unique experiences, and Lewes delivers by celebrating its maritime heritage with a working shipyard. A visit to Lightship Overfalls is a must for hands-on shipbuilding fun. For more history, the Zwaanendael Museum, styled after a 17th-century Dutch town hall, commemorates Lewes’ early settlers and is a fascinating stop.

On the other hand, Cape Henlopen State Park offers a tranquil escape, complete with osprey nesting areas, WWII observation towers, and scenic hiking trails. Those confused about how to truly experience the town can take a walk or bike ride along the scenic Junction and Breakwater Trail, which connects Lewes to nearby Rehoboth Beach and offers incredible views along the way.

Milton

Milton, Delaware, U.S.A.
View of downtown Milton in Delaware. Editorial credit: Khairil Azhar Junos / Shutterstock.com

Milton, best known as the original home of Dogfish Head Brewery, has been a hub for craft brewing since the 1990s. The brewery helped put the town on the map, with tours and tastings attracting beer enthusiasts from all over the state. The real treat, though, is how the town celebrates the Milton Theatre—a venue that now hosts live performances, from concerts to silent films with live music accompaniment. This vibrant arts space is a must-visit, especially after exploring the Milton Historical Society. For a peaceful retreat, Wagamons Pond provides a scenic spot for canoeing competitions or simply unwinding by the water. Whether you're here for the beer, the arts, or the outdoors, Milton offers a well-rounded experience worth savoring.

Odessa

The historic Odessa Bank on Main Street in Odessa, Delaware.
The historic Odessa Bank on Main Street in Odessa, Delaware. Editorial credit: Khairil Azhar Junos / Shutterstock.com

Odessa is a small town with a strong commitment to preserving its colonial past. The Historic Odessa Foundation manages most of its historic district, ensuring uniform colonial-style signage and lighting throughout. History lovers will appreciate a visit to the Appoquinimink Quaker Meeting House, a church dating back to 1785 that still hosts monthly Quaker gatherings.

For a different perspective, take a kayak ride along the Appoquinimink River, which winds through the town’s historic district. The town’s well-preserved 18th- and 19th-century homes add to its charm, and visitors can explore the historic homes open to the public, such as the Corbit-Sharp House. In the evening, check out live music at Blue Label Band on Main Street before winding down with a peaceful stroll in Odessa Memorial Park.

Laurel

Historic colonial home in downtown Laurel, Delaware.
Historic colonial home in downtown Laurel, Delaware. Image credit Dee Dalasio via Shutterstock

Laurel is blessed with the scenic beauty of the Nanticoke River, providing visitors with plenty of scenic spots to explore, such as Lakeside Manor, where you can enjoy peaceful lakeside walks, and Broad Creek, known for its kayaking opportunities. Records Pond is another serene location, perfect for birdwatching or a quiet picnic. For outdoor enthusiasts, Roger C. Fisher Laurel River Park has gorgeous hiking trails, fishing, and peaceful spots to relax by the water. After enjoying the natural beauty, be sure to visit the Laurel Heritage Museum, where the well-preserved old train station gives a glimpse into the town's history. The museum offers free tours, allowing you to delve deeper into the area's past. For a bit of thrill, challenge yourself at The Cemetery House, a haunted attraction that is especially active during Halloween, providing a spine-chilling experience for those brave enough to enter.

Bridgeville

Former Bridgeville Public Library in Bridgeville, now a curio shop.
The former Bridgeville Public Library is now a curio shop.

A small town steeped in rich farming traditions, Bridgeville is known for its apple and watermelon crops. In fact, the community hosts the annual Apple-Scrapple Festival, celebrating the local fruit and, more interestingly, scrapple, a pork-based dish. There is a local legend that says eating scrapple in Bridgeville brings lifelong luck, but there is only one way to find out. A visit to Bridgeville also means a visit to the Bridgeville Historical Society Museum. There is so much agricultural history here that one should know if they were ever in town. Finally, passing by the home goods store, also known as Apple Scrapple downtown, is a must before leaving.

Smyrna

Aerial view of the water tower in Smyrna, Delaware.
Aerial view of the water tower in Smyrna, Delaware.

Originally called Duck Creek Crossroads, Smyrna was renamed in 1806 after the ancient Greek city. The town is full of surprises, from the historic Smyrna Opera House, built in the 1870s and still hosting live performances, to its unusual town ordinance allowing residents to keep chickens on their properties.

For nature enthusiasts, a short trip to Bombay Hook National Wildlife Refuge reveals stunning tidal salt marshes that provide some of the best birdwatching opportunities in the region. The town’s location near the Smyrna River also makes it an excellent spot for boating and fishing. Walking along the historic downtown area, visitors can discover charming cafés and antique shops, adding to the town’s distinct personality.

Rehoboth Beach

The boardwalk at Rehoboth Beach, Delaware.
The boardwalk at Rehoboth Beach, Delaware. Editorial credit: Khairil Azhar Junos / Shutterstock.com.

Originally established in 1873 as a religious summer retreat by a Methodist minister, Rehoboth Beach has transformed into a lively coastal getaway. Its mile-long boardwalk is lined with nostalgic attractions, from classic arcades to saltwater taffy shops. If you wander down Baltimore Avenue, you’ll find the Clear Space Theatre Company, which stages live plays year-round.

To glimpse the town’s past, visit the Rehoboth Beach Museum, which showcases artifacts from its mid-century development as a vacation hotspot. Nature lovers can explore the nearby Gordon’s Pond Trail, a scenic pathway offering stunning wetlands and local wildlife views. And for thrill-seekers, Funland’s vintage amusement park has a haunted house ride that locals argue is the best in the region.

Final Thoughts

All travelers should keep in mind leaving room for the eccentric. There are all sorts of experiences to have and different flavors to taste around the Â鶹AV, but Delaware, of course, has its own unique tang. Its friendly people, historic venues, and stunning coastal areas make for a perfect getaway, especially if one is tired of the commercial and worn-out. Ultimately, it is important to make the most of every moment and embrace various experiences rather than just follow the mainstream.

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