Delaware’s Rehoboth Beach and it’s shops along the boardwalk, Penny Lane Mall. Image credit Foolish Productions via Shutterstock

11 Best Small Towns To Visit In Delaware

Delaware is the oldest state in the union, but native tribes, known as the Delaware or Lenni Lenape, resided in the region long before the arrival of the Dutch and English. Legendary figures like Captain John Smith once traversed the lands of Delaware as he explored the nearby Chesapeake Bay area. While most people think of cities like Wilmington when hearing about Delaware, the small towns should not be overlooked. From beach towns to charming agricultural landscapes, Delaware’s small towns offer diversity, history, and excitement for anyone looking to visit.

Dewey Beach

Pedestrians crossing the road near Dewey Beach
Pedestrians crossing the road near Dewey Beach. Image credit Khairil Azhar Junos via Shutterstock

Dewey Beach is a gorgeous little beachfront town in eastern Delaware. Resting along Delaware Bay gives this beach town an ideal ocean environment for tourists and locals alike to enjoy boating, fishing, swimming, and surfing. Dewey Beach hosts massive bonfires on the shore every Wednesday night during summer. S'mores and other goodies are a popular treat for adults and kids alike. 

But if you're not a fan of swimming, don't worry! There's plenty to do in the small town's two-block radius. One of the best day trips is the John Waples Memorial Playground at 122 Dagsworthy Street. This park is small, but it provides a fun experience for children visiting the town and allows adults to relax and enjoy the city's natural beauty. Close up the day at one of the many high-standard restaurants and nightclubs. The Nalu Surf Bar is the best spot for a mixture of nighttime beach vibes and delicious fresh seafood.


Handmade Gourd Crafts Booth at the Annual Peach Festival in Wyoming, Delaware.
Handmade Gourd Crafts Booth at the Annual Peach Festival in Wyoming, Delaware. Image credit Foolish Productions via

Wyoming is a beautiful, tranquil, historical Kent County, Delaware community. Founded in the 1850s near the Pennsylvania Railroad and the first Methodist Church was built a decade later. Around this time, the town's main export, peaches and apples, became more prominent economically. 

Visitors can taste Wyoming's rich, fruity past by visiting Fife's Orchard. This beautiful farm boasts over 20 varieties of apples and highly praised peaches. They also host events throughout the year, with their annual fall festival being one of the main attractions. Be sure to see Wyoming Park, which offers peaceful scenery, plenty of fun for children, and great fishing.


The aerial view of the waterfront homes with a private dock near Millsboro, Delaware,
Waterfront homes with a private dock near Millsboro, Delaware.

Millsboro is an idyllic location for commerce and families in Salisbury County. Its location along SR 20, 24, 30, and US 113 gives it a unique position as a central connection point and, thus, an economic main point. A robust local economy makes Millsboro an excellent place for families to move to and a great place to visit. 

As an economic hub, it attracts a lot of different businesses that make for a unique experience. One of the best places to spend a lazy afternoon is New Relaxation Massage Parlor. After relieving the stress of your travels, visit the Nanticoke Indian Tribe Museum. This museum offers a unique dive into the history and culture of the First Peoples and the impact they had on Delaware.


Main street in Milton, Delaware.
Main street in Milton, Delaware. Image credit Khairil Azhar Junos via

Milton is a charming, quiet neighborhood in Sussex County. Known for its hospitality and natural beauty, it also has a lot of fun events, social gatherings, and local establishments to attend across the town. Dogfish Head Craft Brewery is an excellent place to visit if you want a taste of local culture, food, and drink. 

However, if you are in the mood for first-rate music, dance, and artistic expression, check out the Milton Theater. Some notable upcoming events include the Peek-A-Boo-Neo-Burlesque Show and the Charlie and the Cool Tunes performance. 


Auto ferry on river, Woodland Ferry, Seaford, Delaware.
Auto ferry on river, Woodland Ferry, Seaford, Delaware.

Seaford is a gorgeous small agricultural community in Sussex County. It's a town steeped in a rich and diverse history stretching back to before the arrival of Captain John Smith in 1608. The first settlers arrived in the region in the 1670s and began the community of Seaford, named after its parent village in England.

Many historical sites preserve the fantastic history of this town, including the Seaford Museum and the Ross Mansion and Plantation. The museum offers a chance to look over the many artifacts and industries that made this town great. The Ross Mansion preserves some of the best-maintained architecture from the early years of Seaford for all to see. However, if you enjoy going out and having fun, there is plenty of that in Seaford too. The AFRAM Festival is a great chance to listen to local music, including jazz, blues, and other genres.


The view of the historic buildings on Main Street.
The view of the historic buildings on Main Street. Image credit Khairil Azhar Junos via

The town of Odessa is a beautiful blend of modernity and history. Founded by the Dutch in the 1660s, it initially held the name of Apequinemy after the native name for the region. Later, the English took over the area in the mid-1700s. In the mid-1800s, the town was renamed Odessa after a Ukrainian shipping town along the Black Sea. 

Tourists will surely enjoy the many historic buildings in town, including the Corbit Sharp House, part of the Underground Railroad. After a day of exploring, spend a few hours eating and drinking at the charming and authentic Cantwell's Tavern.

Rehoboth Beach

People enjoying the sun and the sea at Rehoboth Beach, Delaware.
People enjoying the sun at Rehoboth Beach, Delaware.

Rehoboth Beach is one of the best beach sites in Delaware, with a vast selection of family and solo experiences. Jungle Jim's Waterpark is an excellent place for families to spend the day playing in pools, sliding down water slides, and wading in the wave pool. 

However, the beach has plenty of fun events to offer visitors. The Delaware Seashore State Park is the principal place for swimming and tanning. The water is well known for being some of the cleanest in the area. Stay at the Inn at Lewes after a long, tiring, fun day at the beach. The environment is perfect for relaxing and regaining energy to experience another amazing beach day.


View north along Shell Bridge Road just north of Broad Creek in Bethel, Sussex County, Delaware
Shell Bridge Road just north of Broad Creek in Bethel, Sussex County, Delaware. Image credit Famartin via Wikimedia Commons

Bethel is a close-knit community in Sussex County, Delaware. Despite its small population of just under 200 residents, Bethel has a fascinating history and plenty for visitors to see and experience. 

Originally a shipbuilding city in the 1800s, Bethel retains its roots as a maritime town. The Bethel Maritime Museum is the best place to visit to experience the incredible history of its shipbuilding past. They offer fascinating displays and rotating ship models that help educate viewers on how they made these fantastic ships. 

New Castle

Immanuel Episcopal Church in New Castle.
Immanuel Episcopal Church in New Castle.

New Castle holds a beautiful tapestry of history well-preserved in its authentic buildings throughout the town. With cobblestone streets and vibrant gardens, this town looks like it comes straight out of a storybook. Historic downtown New Castle is the oldest town in Delaware, with continual occupation, since its founding in 1651. The Dutch were the first Europeans to settle the region. However, it traded hands between the English and Swedish throughout its history before finally resting in the hands of the United States.

If you love history, New Castle is perfect for you. The New Castle Court House Museum is one of the oldest courthouses in the United States. Constructed in the 1680s and rebuilt in 1732, the museum offers a front-row view of this amazing historic structure. After a day exploring the beauty of this city, kick back and relax at the Terry House Bed and Breakfast. This lovely spot offers homely rooms and a crisp, clean environment.


Arden craft house, Delaware
Arden craft house, Delaware.

The Village of Arden is a unique town in northern Delaware. This gorgeous village has a short history, having only been founded in 1900 and not incorporated until 1967. However, it has a distinguished history. Arden's history began when the social reformers Will Price and Frank Stephens created the town to encourage artistic exploration with a unique single-tax economy.

To this day, Arden is a city of emotional and spiritual healing. The Labyrinth of Arden is among the most popular places for inner healing and peace. The lovely carving in the ground reportedly provides inner insights and helps you begin your journey of peace and tranquility. Arden is a tiny town, so it only has a little to offer regarding lodging. However, it's just a few miles northeast of Wilmington. You can easily take the day recharging and experiencing the warmth of this small village and spend the evening in the much larger city of Wilmington.


Boardwalk in Smyrna, Delaware
Boardwalk in Smyrna, Delaware.

Smyrna is a small, welcoming town in central Delaware. Located just a few miles from the beach, Smyrna is known for providing an exciting and fun experience for its visitors, even though it's relatively small. The Painted Stave Distillery is an excellent place to spend the evening, mingle with locals, and have first-class homemade meals and drinks.

The Smyrna Opera House is a must-see for any history and music lovers. This rustic yet stunning building wraps both features up in one place. Constructed in 1869, this building retains its original appearance despite nearly being destroyed in the 1940s by fire. It continues to charm its guests with lovely musicals and unforgettable experiences.

Delaware is one of the smallest states in the United States, second only to Rhode Island. Even though it is a little state, it still has much to offer guests. The small towns in Delaware are charming, welcoming and hold a vibrant history. From the beaches at Dewey Beach to the Smyrna Opera House, these locales offer a host of attractions for travelers of all varieties. In addition, a visit to Delaware is not complete without a sampling of the food and drinks, and the state dessert, peach pie, or try the fresh fruit at the many stands along your trip.

  1. Home
  2. Places
  3. Cities
  4. 11 Best Small Towns To Visit In Delaware

More in Places