7 Cutest Small Towns In Delaware
The first state in the nation to ratify the US Constitution, Delaware has always charted its own path. This small-but-mighty state is rich in history, natural beauty, and adorable small towns that are dedicated to protecting its unique heritage. Below we share a list of the cutest Delaware small towns in 2025, all of which are centuries-old and beautifully preserved. In these quaint communities, you’ll find all the ingredients for a memorable vacation — historic sights, fun-filled attractions, stunning scenery, and unforgettable experiences. Cruise the Atlantic Ocean with a crew of pirates, browse the state’s oldest farmers market, hunt for antiques, spend a day at the beach, and attend a colorful Powwow. Whatever your ideal getaway looks like, Delaware delivers.
Lewes
Known as ‘the first town in the first state,’ Lewes can trace its history back to 1631 when European settlers first established a community on the shores of Delaware Bay, where it meets the Atlantic Ocean. Primarily a seaside town, Lewes also has a quaint and walkable downtown with all the main attractions within half a square mile. Tour the town with Historic Lewes, which offers several different types of guided tours, including a 60-minute ‘History Highlights’ excursion and a 90-minute ‘History & Legacy of the African American Community in Lewes’ tour. One of the most striking buildings in Lewes’ cute downtown is the Zwaanendael Museum. Modelled after the town hall in Hoorn in The Netherlands, the eye-catching museum tells the story of Delaware’s first European settlement by the Dutch in the 1600s.
If you’re visiting Lewes with kids, treat them to a swashbuckling adventure with the Pirates of Lewes Expeditions. Running all summer long, this family-friendly cruise gives kids the chance to dress up as pirates and become the cutest captains on the high seas. There’s music, dancing, face-painting, and even a mock battle with water cannons. The voyage lasts an hour and departs three times daily during the season.
Odessa
Historic Odessa in northern Delaware is a trip through time. Known for its classic Colonial-era charm, with a beautiful tree-lined Main Street, Odessa was established in the 1660s by Dutch settlers. The town is home to a National Historic Landmark, the Corbit-Sharp House. The 22-room mansion, built in 1774, is considered Delaware’s finest example of pre-Revolutionary architecture. Now a museum, you can tour the house to see its 18th-century furnishings and learn about its role in the Underground Railroad. Another historic must-see is Cantwell’s Tavern, an 1822 inn that’s now a restaurant serving tasty farm-to-table meals.
The Historic Odessa Foundation manages many of the town’s notable landmarks while also organising seasonal events throughout the year. Visit on the first Saturday after Labour Day to join the festivities at the annual Odessa Brewfest. With live music, food vendors, and a wide selection of regional and national craft beer, this is one of the most popular events on the town calendar.
Milford
Cute and creative, Milford is home to the longest-running farmers' market in Delaware. Now in its 30th year, the Riverwalk Farmers’ Market takes place downtown on Saturday mornings from May through October, offering fresh local produce, baked goods, prepared meals, and arts and crafts items. See more artistic creations at the Mispillion Art League, a downtown studio that offers workshops for local artists while also displaying and selling their work in its gift shop and gallery.
Located on the banks of the Mispillion River, Milford has a long history of shipbuilding, which began when the town’s shipyard was built in 1782. Learn about this fascinating era in Delaware’s past at the Milford Museum, which has exhibits not just on shipbuilding but also military history, black history, and a room devoted to Delaware’s official state bug, the ladybug.
One of the prettiest spots in Milford is the Abbott’s Mill Nature Center. A 376 acre preserve that includes a historic working gristmill, the center features woodland hiking trails, a boardwalk, picnic, gardens, and a Visitor Center with wildlife displays and exhibits.
Rehoboth Beach
One of Delaware’s most popular resort towns, Rehoboth Beach is a laid-back, summery, cute town on the Atlantic Coast. Breathe in the fresh sea air with a rejuvenating walk along the town’s iconic Rehoboth Beach Boardwalk, a mile-long walkway along the shore that’s lined with restaurants and shops on one side and the town’s wide sandy beach on the other.
Be sure to stop at Dolle’s Candyland to pick up some classic seaside treats, such as saltwater taffy, fudge, and caramel corn. A local institution, Dolle’s has been serving visitors since 1927, and its candy creations are still freshly made on the premises. For more old-fashioned beachside entertainment, plan a visit to Funland Amusement Park. With 18 rides, 15 midway games, and a spooky Haunted Mansion, everyone in the family will enjoy a day out in the park.
Smyrna
The former state capital and shipbuilding town, Smyrna, was founded in the mid-1700s. First known as Duck Creek Crossroads, it changed its name in 1809 and became one of the busiest shipping hubs in central Delaware by the 1900s. The town has preserved several of its most historic buildings, two of which now house the Smyrna Museum. The Plank House and the Barracks date back to the 1700s and are open on Saturday mornings for visitor tours.
See more Smyrna history at The Painted Stave, a small batch distillery housed in a historic former theatre. Serving small-batch spirits and cocktails made with regional ingredients, the distillery also features a taco truck on-site, a gift shop, and a covered outdoor patio. Explore Smyrna’s beautiful surroundings at Lake Como, which boasts one of the best swimming beaches in the state, and Blackbird State Forest, which offers a variety of hiking paths as well as a 0.5-mile accessible nature trail.
Millsboro
Located in southern Delaware, on the banks of the Indian River, Millsboro is a pretty town known for its beautiful scenery and old-world charm. It’s also an antiquing hotspot where you can spend hours browsing the boutiques to find the perfect, one-of-a-kind souvenir.
Stop into Black Cat Antiques, formerly known as Antiques Alley and a Millsboro landmark, where you’ll find three storeys of vintage items from around 60 local dealers including jewellery, keepsakes, clothing, furniture, and more.
Millsboro is home to the only Native American museum in Delaware, the Nanticoke Indian Museum. A National Historic Landmark, the two-room museum showcases artifacts handed down through generations from Nanticoke elders, as well as displays on Indigenous tools, villages, clothing, and artwork. The gift shop offers a selection of authentic Nanticoke crafts and memorabilia from the annual Nanticoke Powwow which takes place in September and features drumming, dancing, storytelling, and more than 40+ Native American vendors from across the country.
New Castle
Colonial New Castle is a picturesque town with cobbled streets, a historic riverfront district, and tranquil green spaces. Founded in 1651, the town changed hands many times thanks to its strategically important location on the river and that mix of European influences is still seen today in its architecture and attractions.
A lot of history was made in New Castle. Visit the New Castle Court House Museum, built in 1732, to see Delaware’s first court and state capitol. The building is one of the oldest courthouses in the United States and a National Historic Landmark. Go back even further into New Castle’s storied past with the New Castle Historical Society which operates two museums, the 1690 Dutch House and the 1738 Amstel House. The former looks at life in a 17th-century Dutch colony, while the latter explores the history of New Castle during the pre-Revolutionary War period.
Grab a bite in historic surroundings at Jessop’s Tavern. Over three centuries old, the tavern was built in 1674 and is named for local barrel-maker Abraham Jessop, who opened his business on the premises in 1724. Now a European-style restaurant, it’s also a great place to quench your thirst — the tavern carries over 200 Belgian beers and won the Delaware Reader’s Choice Best Beer Selection award.
Fun In The First State
Delaware’s hidden gem small towns offer a vacation like no other. Cobblestone streets, busy boardwalks, white picket fences, and historic homesteads make the First State’s small towns as cute as a postcard, but don’t underestimate them. There’s plenty to keep you occupied as these historic communities are packed with modern-day attractions and activities.
