Summary
Established in 1787, Delaware became the first official state in modern United States history. Presently, it ranks among the smallest states in terms of both area and population. Numerous small towns are dispersed throughout the state, featuring well-preserved historical edifices, parks, and natural landscapes. Notably, nearly every small town you visit has contributed significantly to American history. Although many may appear similar, each town possesses a unique character that visitors can fully appreciate only through personal exploration.
Delaware attracts travelers owing to its historical landmarks and museums, impressive sites, welcoming communities, and serene living conditions. Along the coastline, expect to find vibrant houses, nautical activities, pristine beaches, and agreeable climates. Some beach towns are bustling, whereas others promise tranquility. Inland, wildlife sanctuaries, garden pathways, and historic mansions await. Additionally, there are numerous references to ancient Native American culture.
If shopping is a passion, Delaware is an ideal destination since it imposes no sales tax. Many boutiques, artisans, and high-end retailers leverage this advantageous situation, resulting in superior shopping venues in this petite state. For those touring along the East Coast, keep some space in your suitcase for Delaware.
Here are the 15 best small towns to visit in Delaware:
1. Clayton
Between 1850 and 1950, Clayton functioned primarily as a railroad town, recognized for its transportation of peaches and for being part of Delaware’s inaugural railroad. Visitors can gain insight into this historical background by exploring the Red Brick Monument at Clayton Station.
Culturally, Clayton hosts a variety of activities despite its modest size. Enjoy live performances at the Smyrna Opera House, the Schwartz Center for the Arts, or children’s plays at the Children’s Theatre of Dover and Kent County. Clayton serves as an excellent base for excursions to the nearby Civil War Fort, allowing visitors to learn more about the period from the Union’s viewpoint.
2. Odessa
Odessa is an 18th-century village that prides itself on preserving its colonial identity. A range of events are available for visitors, centered on re-enacting historical life—such as heart cooking workshops hosted by the Historic Odessa Foundation. Most buildings in Odessa are recognized on the National Register of Historic Places, and guided tours are offered through the scenic blocks.
Enjoy a drink at Cantwell’s Tavern Restaurant, search for antiques, and savor hearty meals at local eateries. Consider visiting during the Christmas season for a distinct and unforgettable experience.
3. Milton
Outdoor enthusiasts will appreciate the sun-drenched activities available in Milton, a small town located near the Broadkill River and the Edward H. McCabe Preserve. Here, options for recreation include fishing, kayaking, hiking, stand-up paddleboarding, and wildlife observation. Alternatively, embark on a boat cruise for a relaxing experience.
The town boasts farmer’s markets, historic structures, spas, art galleries, shops, and innovative craft beers from the Dogfish Head Brewery. For a true taste of local culture, visit during vibrant festivals such as the Horseshoe Crab and Shorebird Festival, Broadkill Banjos and Seafood Festival, or the Holly Festival.
4. Kitts Hummock
Kitts Hummock is a coastal small town characterized by its tight-knit community that welcomes visitors when sunny weather prevails. Since the late 1700s, Kitts Hummock Beach has served as a favored retreat for countless Americans. Today, remnants of colonial cottages, a local tavern, and a number of bed and breakfast accommodations punctuate the area.
Kitts Hummock is home to the Dickinson Plantation, Ted Harvey Conservation Area, and the Saint Jones Reserve. Both residents and out-of-state guests frequent Kitts Hummock Beach as a popular vacation destination.
5. Bowers
Bowers evokes a sense of nostalgia with its motto, “The Way Life Used to Be.” Individuals who enjoy water-based activities such as kayaking, boating, swimming, or fishing will find themselves at home along the shores of this quaint beach community. The local residents are warm, welcoming, and diverse—expect to find yourself on a first name basis with them in no time. Explore the region via a boat cruise or visit the Bowers Beach Maritime Museum, which regularly hosts entertaining events like pirate-themed festivals, parades, and live performances.
Dine at cozy restaurants such as The Bayview Tavern for exceptional comfort food or JP’s Wharf for fresh, locally sourced seafood. Bowers also serves as an ideal base for exploring nearby parks, the St. Jones River, and the Murderkill River.
6. Bethel
For those who appreciate historic architecture, Bethel promises a delightful experience with its population of fewer than 200 residents. The Victorian-style buildings were originally constructed by ship carpenters during the town’s tenure as a hub for shipbuilding. Visitors can uncover the town’s fascinating past by touring the Community House, wandering through Bethel Memorial Park, and seeing the residences of prominent ship captains. While mostly featuring Victorian styles, numerous structures actually date back even further.
7. Lewes
Founded in 1631, Lewes is situated at the confluence of the Delaware Bay and Cape Henlopen, adjacent to Cape Henlopen State Park. This charming town is entirely walkable, allowing visitors to spend a weekend exploring museums, dining, and shopping in the historic district without needing to enter a vehicle. Accommodations range from luxurious villas to well-kept campgrounds, catering to various preferences.
Lewes attracts cyclists and hikers who relish navigating the picturesque trails on the Breakwater Trail, Gordon’s Pond Trail, and the beach. Certain trails are accessible for strollers and wheelchairs, providing enjoyable excursions for families and individuals with mobility challenges.
8. Bethany Beach
While many beach resort towns in Delaware can become crowded and chaotic during peak seasons, Bethany Beach provides a serene escape. Whether traveling with family or alone, visitors will appreciate the calming atmosphere of this coastal town.
Consider visiting during the Bethany Beach Boardwalk Arts festival, and do not miss the Bethany Beach Farmer’s Market. The beach also serves as an excellent starting point for exploring Assawoman Bay State Wildlife Area. Be sure to savor the catch of the day at Bluecoast Seafood Grille and enjoy the lively ambiance at Mango’s.
9. Millsboro
A stroll down Main Street in Millsboro reveals a welcoming atmosphere highlighted by a “Welcome” banner hanging prominently across the street. This genuine hospitality permeates the small town. Visitors can engage in fishing or boating charters, play golf, or explore the nearby freshwater ponds and streams. The area is also a sanctuary for various bird species, making binoculars a valuable addition to your packing list. A diverse range of accommodation options and homestyle restaurants are available to fulfill visitors’ needs.
Millsboro’s rich cultural heritage is deeply rooted in its history, dating back to the time when the Nanticoke Native Americans inhabited the land. The Nanticoke Indian Museum celebrates this heritage.
10. New Castle
In terms of historic small towns, New Castle is among the best preserved in the entire United States. Cobblestone streets adorned with colonial-style architecture meander around the banks of the Delaware River. The intriguing history of the town, having once been owned by Swedes, Dutch, and English settlers, can be explored at the Historic New Castle Court House Museum. Nearly all gardens are meticulously maintained, particularly those surrounding the Amstel House and Immanuel Episcopal Church.
Throughout the year, New Castle hosts an array of vibrant events, including BBQ festivals, beer festivals, food festivals, and various competitions.
Visitors seeking a glimpse into life as it once was for colonial Americans will find no better example than New Castle.
11. Delaware City
For those intrigued by the supernatural, Delaware City possesses a captivating ambiance, enhanced by the presence of resident ghosts. Additionally, it serves as a primary access point to Pea Patch Island—a fort at Fort Delaware that functioned as a prison for the Union Army during the Civil War. To connect with the spirits of history, consider participating in a ghost tour at the fort or attending the Paranormal Expo.
Beyond its eerie attractions, the town offers a variety of events, including cruise nights, concerts, canal festivals, craft fairs, fitness competitions, and antique shows. The tranquil waters surrounding Delaware City provide opportunities for boating and fishing.
12. Seaford
Seaford is a coastal small town abundant in parks, historical landmarks, and various attractions. Most notably, the Ross Mansion and Plantation, previously owned by former governor William Ross, offers guided tours that delve into the site’s somber Civil War history. The Seaford Museum showcases Native American artifacts, Revolutionary War documents, and other engaging historical exhibits.
During the Christmas season, Seaford hosts the largest parade on the Delmarva Peninsula, renowned for its exceptional entertainment and festive cheer. In the summer, the Nanticoke Riverfest features activities such as floating down the Nanticoke River on innertubes or stand-up paddle boards.
Seaford also serves as an ideal base for exploring nearby attractions, including the Woodland Ferry, the U.N.O.I. Mill, and the Patty Cannon House.
13. Wyoming
Envision a serene pond bordered by manicured lawns, playgrounds, recreation areas, and picnic facilities—all of which can be found at Wyoming Park. This small town, which self-identifies as “the best,” emphasizes the development of a strong sense of community and comfort.
Interestingly, Wyoming is most renowned for its peaches, exemplified by the annual Peach Festival that features all varieties of peach pies, peach-flavored ice cream, and tours of Fifer Orchards—the largest peach orchard in the state.
14. Rehoboth Beach
Vibrant, dynamic, and never mundane, Rehoboth Beach is an optimal destination for adventurous travelers eager for a seaside experience. Amble along the restaurant-lined boardwalk, stroll along the shoreline, and listen for local musicians performing at no charge. The town is frequented by a diverse, artistic crowd who display their talents in boutique art shops and galleries. Dining options in Rehoboth Beach reflect a high standard, typically accompanied by a lively ambiance, making it essential to come hungry and ready for dessert.
The town hosts four large parks for relaxation and is conveniently located near Cape Henlopen and Delaware Seashore state parks.
15. Arden
Arden is perhaps one of the most fascinating small towns in Delaware, if not the entire nation. It was founded by two utopian architects dedicated to establishing a single-tax community focused on equality and cooperation. Homes designed by founder Will Price are listed on the National Register of Historic Places. Residents prioritize simplified spellings, support live theater (especially performances by the Shakespeare “Gild”), and welcome visitors from all walks of life.
Visiting Arden calls for an extended stay to fully appreciate what the community offers, as it is the people who truly define the experience rather than mere attractions.
