13 Must-Visit Delaware Towns That Charm Visitors Every Summer

DELAWARE — While the First State may be small, Delaware packs in an impressive mix of history, small-town charm, and coastal escapes that make it a top summer destination. From quiet beach towns like Fenwick Island to bustling hubs like Rehoboth Beach, these communities offer something unique — whether you’re looking for family-friendly fun, rich historical walks, or relaxing waterfront sunsets.

Here are 13 of the most charming Delaware towns to explore this summer.

1. Lewes – The First Town in the First State

Lewes lives up to its motto. It’s home to the Zwaanendael Museum, preserving its Dutch colonial roots, and Cape Henlopen State Park, where visitors can climb a towering 80-foot dune or relax on historic beaches tied to the Underground Railroad.

Don’t miss the Lightship Overfalls, a floating museum, or a scenic ride on the Cape May-Lewes Ferry — often a dolphin-spotting highlight.

2. Rehoboth Beach – The Nation’s Summer Capital

Founded in 1873, Rehoboth’s mile-long boardwalk is still a favorite for beachgoers. The Funland Haunted Mansion has spooked generations since 1962. With free Bandstand concerts, Tuesday farmers markets, and a rich local museum, Rehoboth delivers heart and history alongside the ocean breeze.

3. Milton – Home of the Holly Festival and Dogfish Head Brewery

Once called the Holly Capital of the World, Milton still celebrates with an annual winter festival. Stroll along the Broadkill River or catch a show at the Milton Theatre, active since 1910. Beer lovers make pilgrimages to the Dogfish Head Brewery, while architecture fans admire preserved homes like the Gov. James Ponder House.

4. New Castle – Where Colonial History Comes Alive

New Castle dates back to 1651 and boasts one of the best-preserved historic districts in the U.S. Visit Immanuel Church, standing since 1703, and walk The Green, the site of Delaware’s first capital. The Kalmar Nyckel replica offers an immersive 17th-century sailing experience when docked nearby.

5. Bethany Beach – A Quiet Resort With Big Personality

Bethany keeps it low-key with a half-mile boardwalk filled with shops and live music. Chief Little Owl’s statue greets visitors, while the Nature Center offers wetland trails perfect for nature walks. The town’s engineered dunes protect the coastline, and its Fourth of July parade draws families year after year.

6. Fenwick Island – For Peace, Fudge, and Lighthouse Views

Known for peaceful shores and a slow pace, Fenwick Island is ideal for travelers avoiding the beach-town hustle. The Fenwick Island Lighthouse, standing since 1858, is open for tours. Don’t skip the Seaside Country Store — famous for its 30+ fudge flavors — or Thunder Lagoon Waterpark for family fun.

7. Middletown – Festivals, Film, and Historic Pride

Every August, the Olde Tyme Peach Festival fills the streets with food, music, and parades. The town’s charm also includes St. Andrew’s School, a filming location for Dead Poets Society. Cochran Square and the Middletown Academy are steeped in history, while Crooked Hammock Brewery offers modern-day chill.

8. Dewey Beach – Where the Bay Meets the Atlantic

Framed by the ocean and Rehoboth Bay, Dewey Beach is a sunset-lover’s paradise. The town hosts skimboarding championships, beachfront movie nights, and welcomes leashed dogs on the sand — a rare find in many U.S. beach towns.

The Starboard, a bar from the 1960s, keeps the nightlife energetic and nostalgic.

9. Laurel – Historic Homes and Cypress Trees

With the largest historic district in Delaware, Laurel is a must for history buffs. Explore Trap Pond State Park, home to the northernmost bald cypress swamp in the U.S., or ride the Broad Creek Bike and Brew for beer and exercise. Dutch Country Market offers Amish treats perfect for picnic stops.

10. Odessa – A Step Back into the 18th Century

Once known as Cantwell’s Bridge, Odessa preserves 18th-century life through the Historic Odessa Foundation. Sites like the Corbit-Sharp House feel frozen in time. At Cantwell’s Tavern, diners enjoy historic ambiance with modern flavors. Odessa Brewfest and holiday home tours round out the year’s festivities.

11. Georgetown – Where Unity and Heritage Thrive

Located “16 miles from everywhere,” Georgetown embraces unity during its Return Day, when election results are read aloud and a symbolic hatchet is buried. Explore the Marvel Carriage Museum or visit during Festival Hispano, which showcases Delaware’s growing Latino community through food, music, and dance.

12. Harrington – Where Tradition Meets Fun

The Delaware State Fair transforms Harrington into a summer hotspot, drawing over 300,000 visitors for concerts, carnival rides, and fried delicacies. Afterward, Harrington Raceway & Casino keeps the excitement alive. Don’t miss the Greater Harrington Historical Society’s train tower and seasonal ice skating at Centre Ice Rink.

13. Wyoming – The Small-Town Peach Capital

While not included in the original list, Wyoming, Delaware deserves an honorable mention. Its Wyoming Peach Festival in August rivals that of Middletown, with a charming small-town feel that continues to attract summer visitors.

Plan Your Summer Getaway

From quaint boardwalks to historic churches, festival-packed streets to quiet forest walks, Delaware’s towns offer a taste of something timeless. Whether you’re traveling with family, on a romantic getaway, or road-tripping through the Mid-Atlantic, these towns make perfect summer stops.

What’s your favorite small-town summer spot? Let us know in the comments or share your Delaware travel photos with us at SaludaStandard-Sentinel.com.