7 Prettiest Small Towns In Delaware

As the first colony to ratify the new US Constitution, Delaware is a window into America's founding, and its small, scenic towns display that history in their beautiful streetscapes. Discover the coastal beaches and boardwalks of Bethany Beach, which features summer concerts through the Bethany Bandstand. The red brick Georgian homes and Mispillion Riverwalk Park in Milford are ideal for a lovely stroll. And then there is Cape Henlopen State Park in Lewes, which contains 5,000 acres of beaches and forest trails. Our list of the prettiest towns in Delaware should give you plenty of inspiration for a road trip, weekend getaway, or a day out.

New Castle

Pack your walking shoes if you’re going to New Castle, as you’ll want to wander the cobblestone streets of this pretty riverfront town. Founded by Dutch settlers in the 1650s, New Castle has preserved much of its past with its charming Colonial-era historic district designated a National Historic Landmark.

The New Castle Historical Society operates two historic house museums downtown, the c. 1690 Dutch House and the 1738 Amstel House. The former shows what life was like in a 17th-century Dutch colony, while the latter was the home of Governor Nicholas Van Dyke during the Revolutionary War. New Castle also contains two locations within First State National Historic Park, the Sheriff’s House Welcome Center and the New Castle Courthouse Museum, built in 1732 and once the location of Delaware’s first courthouse and state capitol.

If you’re in town on a Friday, you’ll get a chance to see some colorful artwork taking over downtown. New Castle hosts Art On The Town, the fourth Friday of every month except December, during which businesses, restaurants, and historic sites show exhibitions and displays.

Bethany Beach

Wide, sandy beaches, sundrenched boardwalks, and sweeping coastal views make Bethany Beach one of Delaware’s most picturesque towns. Stroll the half-mile Bethany Boardwalk to enjoy the fresh, salt air rolling off the Atlantic Ocean and visit the town beaches. The boardwalk leads to the Bethany Bandstand, which hosts summer concerts featuring local musicians, as well as seasonal festivals and fairs.

Bethany Beach is also one of the gateway towns to explore two beautiful recreation areas, Fenwick Island State Park and Assawoman Bay State Wildlife Area. Each offers hiking trails with incredible waterfront views, pristine beaches, and coastal wetlands. There are also facilities for kayaking, swimming, surfing, and sailing.

Lewes

Named one of ‘The Most Beautiful Towns in America’ by Conde Nast Traveler, Lewes is a pretty community on the Delaware River with a long history. The town was established in 1631, earning it the nickname of ‘the first town in the first state’ and giving it beautiful architecture as well as picturesque waterfront views.

One of the most eye-catching landmarks in town is the Zwaanendael Museum, built in 1931. The museum tells the story of Lewes, from its early Dutch heritage to its thriving maritime industry. For more on Lewe’s maritime heritage, visit the Overfalls Lightship, a National Historic Landmark built in 1938 and now a floating museum docked in the canal. The museum is open during the summer season and offers tours of the boat so visitors can experience life above and below decks on a working lightship.

Lewes is the location of one of Delaware’s prettiest parks, Cape Henlopen State Park, which protects 5,000 acres of beaches, coastline, and maritime forest. The park contains 8 scenic walking trails, a Seaside Nature Center, and a historic fort. For the best views, head to The Point, where you can climb the sand dunes to look out over where Delaware Bay meets the Atlantic Ocean.

Milford

With three historic districts on the National Register of Historic Places and a renowned riverwalk, Milford is one of Delaware’s gems. Laid out in 1787, this quaint mill town on the shores of the Mispillion River is a must-see for daytrippers and vacationers alike. One of the best ways to see the town is via the Mispillion Riverwalk Park, a mile-long greenway that runs through the heart of downtown. Also downtown is the Parson Thorne Mansion, a red brick Georgian home built in the 17th century and surrounded by beautiful gardens.

Odessa

Historic Odessa is a tiny town, trapped in time. Home to just over 300 residents, the entire village is a National Registry District and one of only 13 National Historic Landmark sites in Delaware. It can trace its history back hundreds of years to the 1600s when Dutch pioneers settled the area.

The most historic and beautiful buildings in town are managed by the Historic Odessa Foundation and include the Corbit-Sharp House, a 22-room mansion built around 1774. The home, considered Delaware’s finest pre-Revolutionary house, is now a museum decorated with 18th century furnishings and displaying a collection of period antiques.

Visit the Odessa Bank to see one of the few remaining historic commercial buildings in town. Built in 1853, it operated as a bank until 2000 but is now the headquarters of the Historic Odessa Foundation, where you can pick up a town map, browse the exhibits, or check the events schedule. After exploring the picturesque streets of Odessa, grab some refreshments at another piece of the past, Cantwell Tavern. This Federal-style country inn was built in 1822 and is now a restaurant offering farm-to-table dishes and craft brews.

Smyrna

Known as Duck Creek Cross Roads when it was founded in 1755, Smyrna is a Colonial-era town on the shores of Lake Como where you can shop, sightsee, and spend a day at the beach. The lakeshore’s swimming area is open from Labor Day to Memorial Day, but it is a beautiful spot for a walk year-round.

The town is also close to another stunning natural recreation area, Blackbird State Forest. Delaware’s northernmost state forest, the preserve has ten tracts open year-round, picnic sites and campsites, as well as a 0.5-mile wildlife and nature interpretation trail.

You don’t have to leave Smyrna for beautiful views. The historic Opera House is one of the prettiest landmarks in town. Built in 1870 and listed on the National Register of Historic Places, it’s now a thriving cultural arts center. Another historic building, Belmont Hall, dates back to 1773 and is open for tours of the restored Georgian mansion and landscaped grounds.

Delaware City

Despite its name, Delaware City is a quiet riverside town in the Wilmington area with access to beautiful waterfronts, canalside trails, and historic forts. Take the ferry to Pea Patch Island to explore Fort Delaware State Park. The fort was built in 1859 and, despite being active during the Civil War, Spanish-American War, WWI, and WWII, never fired a single shot in combat. Today, you can tour the parade ground, officers' quarters, barracks, kitchen, blacksmith shop, and ordnance room. The fort is open to the public from June to October.

If Fort Delaware is too busy, check out Fort DuPont, built to protect the port cities along the Chesapeake and Delaware Canal. Now Fort DuPont State Park, the park is a prime spot for picnicking, birdwatching, and nature walks. Take the Riverview Trail to see beautiful views of the Delaware River while meandering past three military barracks.

There are more waterfront views along the Chesapeake and Delaware Canal Trail, which runs 12.1 miles along the north shore of the 1800s canal route. Delaware City lies at the eastern end of the trail, and you’ll find the trailhead near the bottom of the Reedy Point Bridge. Keep your camera ready, and your eyes peeled, the trail is home to a lot of local wildlife, including deer, turkeys, raccoons, peregrine falcons, pied-billed grebes, and bald eagles.

Dazzling Delaware

Delaware’s big cities have their urban charm, but the state’s small towns are where you’ll find the best views and the most unique experiences — wander the beachside boardwalk, tour a Revolutionary War home, hear the cannons fire at an 1800s fort, or just enjoy a shady picnic under the canopy of the state’s northernmost forest. The best time to visit Delaware is in the spring when the weather is warming, but you can still escape the summer crowds. Many of the attractions on our list are seasonal, so it’s a good idea to check the schedules before you visit.