15 Best Small Towns to Visit in Delaware

Written by Chantae Reden
Updated on
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Back in 1787, Delaware was created as the first official state in the modern United States. Today, it’s one of the smallest in both size and population. Small towns are everywhere, most with well-preserved historic buildings, parks, and natural features. Interestingly, nearly small town that you visit will have played a major role in American history. And while many seem similar on the surface, each small town has a distinct personality that you can only get to know by visiting in person.

Travelers love Delaware because of its historic sites and museums, incredible landmarks, friendly communities, and tranquil living. On the coast, expect colorful houses, boating activities, clean beaches, and good weather. Some beach towns are lively while others are solely relaxing. Inland, you’ll easily find wildlife retreats, garden trails, and old mansions. Odes to ancient Native American culture also abound.

If you love to shop, Delaware is the perfect place to visit because there is no sales tax. Many boutiques, artists, and luxury stores have taken advantage of this fact so the quality of shopping centers is top notch in this little state. If you’re doing a trip around the entire east coast of the United States, save that empty suitcase for when you get to Delaware.

Here are the 15 best small towns to visit in Delaware:

1. Clayton

Source: Davidmatthewobrien / Wikimedia

From 1850 to 1950, Clayton was primarily a railroad town that was once known for transporting peaches and part of Delaware’s first railroad. Visitors can get a taste of this history by visiting the Red Brick Monument at Clayton Station.

Culturally, Clayton has a lot going on despite its small size. Watch live performances at the Smyrna Opera House, the Schwartz Center for the Arts, or child-specific plays at the Children’s Theatre of Dover and Kent County. You can use Clayton as a base to visit the nearby Civil War Fort and learn more about the era from the Union’s perspective.

2. Odessa

Source: Lee Cannon from Bayville aka West Fenwick, DE, USA / Wikimedia

Odessa is an 18th century village that cherishes its identity and has managed to maintain its colonial heritage. There are all types of events for visitors centered around recreating life as it once was – like heart cooking workshops at the Historic Odessa Foundation. Most of the buildings in Odessa are on the National Register of Historic Places, and there are even guided walks that weave through the most picture-worthy blocks.

Grab a drink at the Cantwell’s Tavern Restaurant, shop for antiques, and enjoy hearty meals at the restaurants in Odessa. Visit during the Christmas holidays for a truly unique experience that can’t be found anywhere else.

3. Milton

Source: Michele Dorsey Walfred / Flickr
Waples Pond, Milton Delaware

Outdoor lovers will love spending all their time under the sun in Milton, a small town near the Broadkill River and the Edward H. McCabe Preserve. Here, you can fish, kayak, hike, stand up paddle, and explore the wildlife areas. Or, just hop on a boat cruise and spend your time relaxing.

In town, there are farmer’s markets, historic buildings, spas, art centers, shops, and craft beers at the Dogfish Head Brewery. To experience the full community vibe, visit during one of the many festivals like the Horseshoe Crab and Shorebird Festival, Broadkill Banjos and Seafood Festival, or the Holly Festival.

4. Kitts Hummock

Source: mmahaffie / Flickr
Kitts Hummock

Kitts Hummock is a beachside small town with a close-knit community that welcomes visitors once the sun starts shining. Americans have been using Kitts Hummock Beach as a prime vacation spot since the late 1700s, so consider it an American pastime. Today, there are still remnants of colonial cottages, a local tavern, and a handful of bed and breakfast places to choose from.

Kitts Hummock hosts the Dickinson Plantation, Ted Harvey Conservation Area and the Saint Jones Reserve. Both Delaware locals and out of state visitors alike visit Kitts Hummock Beach as resort getaway.

5. Bowers

Source: -Jeffrey- / Flickr
Bowers Beach

It’s easy to feel a sense of nostalgia in Bowers, a small town with the tagline, “The Way Life Used to Be.” Those with a penchant for watersports like kayaking, boating, swimming, or fishing will feel right at home on the shores of this little beach community. The locals are vibrant, friendly, and eclectic – so don’t be surprised if they start referring to you by your first name. You can see the region by a boat cruise or stay landlocked at the Bowers Beach Maritime Museum. The museum frequently hosts fun events like pirate-themed festivals, parades, and live entertainment.

Eat at cozy style restaurants like The Bayview Tavern for great home cooking or JP’s Wharf for a taste of the locally sourced seafood. Bowers also is a great base for exploring the nearby parks, St. Jones River, and Murderkill River.

6. Bethel

Source: jimmywayne / Flickr

If you love old architecture, you’ll love Bethel, a small town with less than 200 residents. The Victorian style buildings were once built by ship carpenters back during the time when the town was a major shipbuilding community. Today, you can get a nice window into its interesting history by visiting the Community House, walk through Bethel Memorial Park, and visit the homes of famous ship captains. And while the architecture is mostly of Victorian style, most buildings actually date back much earlier.

7. Lewes

Source: Jon Bilous / shutterstock

Lewes was founded in 1631 and you can find it where the Delaware Bay meets Cape Henlopen, right next to the Cape Henlopen State Park. This beautiful small town is completely walkable, so you can spend an entire weekend exploring perusing museums, restaurants, a historic district, and boutique shops without ever having to step inside a vehicle. There are a variety of accommodation options ranging from luxury villas to manicured campgrounds to suit your comfort needs.

Lewes also attracts cyclists and trekkers who love weaving through the scenery on the Breakwater Trail, Gordon’s Pond Trail, and along the beach. Some trails are suitable for strollers and wheelchairs, making the trails a fun excursion for families and people with physical disabilities.

8. Bethany Beach

Source: Al Jurina / shutterstock
Bethany Beach

Other beach resort towns in Delaware are often crowded and hectic, especially in the high season. Bethany Beach, however, is a beautiful beach town that offers a much more serene atmosphere. No matter if you’re traveling with family or on your own, you’ll love Bethany Beach as a quiet getaway.

Visit Bethany Beach during the Bethany Beach Boardwalk Arts festival and stop at the Bethany Beach Farmer’s Market. The beach is also a great home-base for the Assawoman Bay State Wildlife Area. In town, be sure to order the catch of the day at Bluecoast Seafood Grille and stop by Mango’s for lively vibes.

9. Millsboro

Source: mmahaffie / Flickr
Millsboro Pond

Walk down Main Street in Millsboro and you’ll find a “Welcome” banner hanging proudly across the road. This warmth and hospitality is found all throughout the small town. You can hop on a fishing or boat charter, go golfing, or even explore the nearby freshwater ponds and streams. The town is also a haven for birdlife, so be sure to add binoculars to your packing list. There are a variety of accommodation options and home-cooked family style restaurants to suit your basic needs while in Millsboro.

Millsboro also has a strongly preserved culture dating back to when the Nanticoke Native Americans had sole custody of the land. Today, their history is celebrated at the Nanticoke Indian Museum.

10. New Castle

Source: Daniel M. Silva / shutterstock
New Castle

When it comes to historic small towns, New Castle is one of the best preserved in the entire country. Cobblestone streets with colonial style architecture wind around the Delaware River. You can learn all about its intriguing past (it was once owned by the Swedes, the Dutch, and the English at some point) at the Historic New Castle Court House Museum. Nearly every garden is perfectly manicured, especially around the Amstel House and Immanuel Episcopal Church.

All year long, New Castle hosts lively events like BBQ festivals, beer festivals, food festivals, and many types of competitions.

If you want to experience life as it once was for colonial Americans, you can’t get closer than New Castle.

11. Delaware City

Source: Bernt Rostad / Flickr
Delaware City

Want to go somewhere spooky? Delaware City has an intriguing aura around it thanks to its resident ghosts that linger around. Delaware City is also one of the only ways to access Pea Patch Island – a fortress at Fort Delaware that was used by the Union Army as a prison in the Civil War. If you want to meet the spirits of the past, you can take a ghost tour at the fort or attend the Paranormal Expo.

Aside from its spooky attractions, there are also events like cruise nights, concerts, canal festivals, craft shows, fitness competitions, antique shows, and much more to experience. The town itself is situated on peaceful waters where you can go boating and fishing.

12. Seaford

Source: Lee Cannon / Flickr
Governor Ross Mansion, Seaford, DE

Seaford is a coastal small town with tons of parks, historic sites, and interesting things to see. Most notably, the Ross Mansion and Plantation was once owned by the former governor, William Ross. On a tour of the plantation, you can learn more about the dark history that took place during the Civil War Era. The Seaford Museum also exhibits Native American artifacts, documents from the Revolutionary War, and other interesting items of the past.

During Christmastime, Seaford hosts the largest parade on the Delmarva Peninsula that goes over-the-top when it comes to entertainment and festive cheer. The Nanticoke Riverfest is a must-attend summertime activity that involves floating down the Nanticoke River on innertubes or standup paddle boards.

Seaford is also the perfect hub for exploring the nearby attractions of Woodland Ferry, the U.N.O.I. Mill, and the Patty Cannon House.

13. Wyoming

Source: jimmywayne / Flickr

Picture a mirror-calm pond surrounded by manicured lawns, playgrounds, game areas, and picnic amenities. This can all be found at Wyoming Park. The little town of Wyoming (self-proclaimed as the best) is focused on building a strong sense of community and comfort.

Interestingly, it’s most famous for its peaches. Every summer, the town puts on the Peach Festival that serves all types of peach pies, peach flavored ice cream, and tours of Fifer Orchards – the largest peach orchard in the state.

14. Rehoboth Beach

Source: Dex Sightseeing Photography / shutterstock
Rehoboth Beach

Colorful, lively, and never boring, Rehoboth Beach is the best place to visit for adventurous travelers who love to spend all their time seaside. Stroll along the restaurant-lined boardwalk, dip your toes in the sea, and keep an ear out for local musicians performing free concerts. The town is known to attract eclectic and artistic personalities, who love to share their work in boutique art shops and galleries. The restaurants in Rehoboth Beach are above standard and usually have a fun atmosphere, so come hungry and save room for dessert.

There are also four major parks to relax at, and Rehoboth Beach is just a short distance from the Cape Henlopen and Delaware Seashore state parks.

15. Arden

Source: fake is the new real / Flickr

Arden is perhaps one of the most intriguing small towns in Delaware – if not the entire country. It was established by two utopian architects who wanted to create a single-tax community that solely focuses on equality and togetherness. Homes designed by the founder, Will Price, are all on the National Register of Historic Places. Citizens believe in simplified spellings, support live theatre (especially performed by the Shakespeare “Gild”), and welcome visitors of all types.

If you visit Arden, you’ll want to stay more than just a few days to gain the full experience. Here, the people make the place rather than the area’s attractions.

15 Best Small Towns to Visit in Delaware:

  • Clayton
  • Odessa
  • Milton
  • Kitts Hummock
  • Bowers
  • Bethel
  • Lewes
  • Bethany Beach
  • Millsboro
  • New Castle
  • Delaware City
  • Seaford
  • Wyoming
  • Rehoboth Beach
  • Arden