9 Prettiest Towns to Visit in Delaware

The oldest state in America, Delaware harbors a rich tapestry of national history woven among its scenic landscapes and shores along the Delaware River and Bay. From its founding in colonial times through the era that shaped our nation’s core values, Delaware’s small towns tell an enlightening story. Spread across the diverse landscapes of the First State; these pretty hamlets have all the hallmarks of a satisfying getaway. From riverfront ports offering a window to bygone trade missions to quaint villages enjoying rebirths as art communities, they reward travelers with captivating history, iconic landmarks, and vistas around each bend.

If you are planning a tour of the East Coast, these exciting towns to visit in Delaware promise an unforgettable vacation, whether a history enthusiast, culinary connoisseur, culture vulture, or outdoor thrill seeker.

Rehoboth Beach

Rehoboth Beach’s tiny population of about 1,200 permanent residents grows over tenfold in the summer as a barrage of beach-loving tourists descend upon the adorable town. Set on the scenic Atlantic Coast, it enjoys stunning beach scenery that complements its cozy, sunny weather. The mile-long Rehoboth Beach Boardwalk presents a popular visitor hub where the young and old converge to explore a blend of family-friendly attractions, from amusement parks and restaurants to beach stores and souvenir shops. The town has ample opportunities for good-natured social interactions, especially at the weekly Rehoboth Beach Farmers Market.

Year-round events and festivals help keep Rehoboth Beach on many travelers’ itineraries, and the Rehoboth Beach Bandstand serves as the town’s primary entertainment center during summer. This open-air venue hosts a string of concerts featuring enthralling live performances.

New Castle

Situated less than 15 minutes from Wilmington, this historic community on the Delaware River offers a relaxed escape from the big city. Thanks to a rich heritage spanning over three centuries, it is the perfect destination for historically inclined travelers. This manifests through the numerous historical sites across the town, housed in rustic buildings with conspicuous red-brick construction. The Amstel House Museum is an excellent example, a well-preserved colonial mansion from the 1730s. Touring the Read House & Gardens delivers a glimpse into the late 18th century inside a Federal-style mansion.

Meanwhile, the Dutch House Museum is one of the town’s oldest structures, dating back to the 1600s. Inside the venue, guests can explore a library of historical information and artifacts documenting Dutch heritage in the area. Beyond this rich past, New Castle welcomes tourists to shop for farm produce, handicrafts, and collectibles at the bustling New Castle Farmers Market.

Lewes

Rich history meets scenic outdoors in this coastal community on Delaware Bay. Lewes was the state’s first European settlement, settled by the Dutch in 1631. Its long and colorful past is preserved at the Lewes Historical Historical Society through old photographs, archives, and artifacts. Visitors can delve deeper into local history at the Zwaanendael Museum, which commemorates Delaware’s first European settlement and is modeled after the former city hall in Hoorn, Netherlands. Touring the facility reveals a selection of artifacts chronicling the region’s social, military, and maritime heritage.

The Historic Lewes Farmers Market supplies residents and visitors with fresh produce straight from the farm, from vegetables and fruits to meats. It also offers an opportunity to mingle with townsfolk and experience local culture. Finally, Pirates of Lewes are among the different outfitters that take visitors on themed boat tours for a unique experience.

Milton

This quaint village in Sussex County lies along the banks of the Broadkill River, which flows into the Delaware Bay. Its origin traces back to 1672 when English colonists settled in the area, later becoming a vital shipbuilding hub. This rich history comes alive in the Milton Historic District, which houses over 150 historical structures from the 1700s to the early 1900s. The Milton Historical Society lures those curious to uncover the town’s past with enlightening exhibits. Milton is also known for its thriving cultural scene, which newcomers can sample by catching entertaining live shows at the Milton Theatre.

Milton Memorial Park assures guests of readily available outdoor opportunities. This riverside reserve offers a chill atmosphere for those who enjoy rich natural settings. It has a nice walking path and picnic spaces, and the Broadkill River is accessible if you fancy a laid-back kayaking or canoeing excursion.

Bethany Beach

First-timers easily fall for the small-town charm and beautiful vistas synonymous with this coastal community. Walking down the Bethany Beach Boardwalk hints at why Bethany Beach is considered among the most charming towns to visit in Delaware. The area boasts a festive atmosphere with a mix of shopping spots, dining outlets, and souvenir shops to explore while taking in the fresh Atlantic breeze. Further inland, the Bethany Beach Nature Center exposes you to gorgeous greenery spread across an approximately 26-acre park with tidal wetlands and forested upland habitats.

Bethany Beach has the ideal vibe for a remarkable family getaway, a credit to attractions like the Shore Fun Family Fun Center. The fabulous facility guarantees wholesome fun for all ages with various entertaining activities, such as pinball machines, arcade games, and air hockey.

Georgetown

Tourists visiting Georgetown keep returning for the immersive historical journey it delivers. The seat of Sussex County has a rich legacy stretching back to the 18th century and harbors numerous landmarks and sites preserving its past. Prominent among these is the Marvel Carriage Museum, which exhibits a collection of restored buildings and antique carriages depicting life in the formative eras. Meanwhile, the Georgetown Train Station documents the town’s railroad heritage inside a 19th-century facility.

With multiple antique shops spread across downtown, guests can leave with a piece of the town to remind them of the experience by shopping at the Georgetown Antiques Market. Art lovers will, however, prefer to get cultured by watching a delightful live performance at Possum Point Players.

Dover

Despite being Delaware’s capital, Dover has a quintessential small-town feel with a population under 40,000 and lovely natural spaces. Most travelers praise the community for its impressive blend of attractions, which caters to all visitor preferences. History enthusiasts are spoilt for choice and can find a treasure trove of sites to explore, including the First State Heritage Park and the Johnson Victrola Museum. Elsewhere, art enthusiasts can look forward to visual and performance art experiences at the Biggs Museum of American Art and the Schwartz Center for the Arts, respectively.

Finally, ardent outdoor enthusiasts will love exploring Silver Lake Park to enjoy its recreational opportunities. This urban oasis features an easygoing and welcoming atmosphere that draws adventurers to stroll along its wooded trails, picnic on its grassy grounds, and fish for striped bass, catfish, and bluegill in Silver Lake.

Middletown

This lovely community of about 25,000 is home to the Delaware Technical Community College. Its welcoming atmosphere and friendly locals allow first-timers to feel at home. This is evident at the Dutch Country Farmers Market, where you can interact with down-to-earth local vendors while combing through diverse Amish delicacies, including fresh baked goods, dairy products, and artisanal candles. The Charles E. Price Memorial Park provides a lovely escape to the great outdoors with its quiet walking trails, peaceful picnic pavilions, and an idyllic fishing pond.

Art lovers and movie enthusiasts can converge at the Everett in downtown Middletown for a compelling cultural experience. This iconic venue hosts varying events to entertain the audience, from local art exhibitions and live stage productions to cinematic films. It was immortalized in the 1989 flick “Dead Poets Society.”

Fenwick Island

Fenwick Island is the perfect Delaware getaway for those seeking an escape from the crowds to unwind and forget all their troubles. With less than 400 people calling it home, tourists can comfortably explore miles of pristine, sandy shores without competition. This is best embodied by the 344 acres of Fenwick Island State Park, which promises a mix of secluded beaches, charming picnic areas, and designated surfing spots. The area’s maritime past comes alive at the DiscoverSea Shipwreck Museum, which displays a collection of treasures salvaged from numerous shipwrecks off the Atlantic Coast.

Guests can also witness and learn about one of the state’s oldest lighthouses by touring the nearby Fenwick Island Lighthouse, a rustic landmark dating back to 1858. Before leaving the island, remember to buy a precious souvenir at the Seaside Country Store to keep the fun memories.

Delaware’s Must-Visit Small Towns

The First State is an inviting destination that lets travelers delve into the landmark years that made America what it is today. However, it also harbors unmatched natural beauty and cultural heritage, which become evident when you explore the most exciting towns to visit in Delaware. From walking along picturesque riverfronts to strolling through well-preserved downtown streets, visitors gain vivid lessons in local history and character. Planning your travel itinerary around any of the above offers the perfect introduction to this enduring home of American tradition.