7 of the Most Walkable Cities in Delaware

Even at its widest point, you can walk across Delaware in a day. At its narrowest, it'll take a couple of hours. In fact, Delaware is so commonly crossed on foot that there's an annual event called Hike Across Delaware, which brings dozens of hikers together for a non-competitive traverse of a 15-mile stretch of the state. But you don't have to walk that far to see Delaware in all its diversity. Small towns have pedestrian-friendly trails lined with historic, commercial and natural attractions that make for leisurely strolls. Here are seven such communities where you can take your first steps in the First State.

Rehoboth Beach

By definition, any community with a boardwalk is pedestrian-friendly. Rehoboth Beach's boardwalk is about a mile long and is lined by its namesake beach on one side and bustling shops on the other. These include Zelky's Beach Arcade, Funland and the Rehoboth Toy & Kite Company. But Rehoboth is pedestrian-friendly far beyond the boardwalk. Side streets are lined with elegant restaurants like Theo's Steaks, Sides & Spirits and Aroma Mediterranean Cuisine, both of which were stops on the Sunday Eating Rehoboth Walking Food Tour. History buffs would be better off taking the Rehoboth Beach Historical Society's walking tour, which includes a stop at the Woman's Christian Temperance Union Fountain, a granite remnant of a much tamer Rehoboth.

New Castle

As one of the oldest communities in Delaware, New Castle's attractions have been around for centuries. Almost all of them are located in the New Castle Historic District, which stretches for several blocks in the city center and includes hundreds of historic buildings. Several guided and self-guided walking tours educate visitors about the district and show off its most magnificent structures, such as the New Castle Court House (ca. 1732), Amstel House (ca. 1738), Dutch House (ca. 1690), Read House & Gardens (ca. 1804), and Old Town Hall (ca. 1823). There is even an audio walk that combines informative clips with a tour of 46 different attractions.

Georgetown

Georgetown is a place where you go in circles, but that's intentional, not madness. This town of about 7,000 residents was laid out in a circular shape. Of course, you should start your tour of Georgetown inside the circle, which was laid out in the 1790s and is now a green park with a picturesque fountain. From there, it's just a matter of walking around the circle to get a centuries-long overview of Georgetown's architecture. Notable historic buildings include the New Sussex County Courthouse (ca. 1840) and the Brick Hotel (ca. 1836). However, not all of Georgetown's buildings are confined to the circle. Along the straight streets stand the Old Sussex County Courthouse (ca. 1792), St. Paul's Episcopal Church (ca. 1844), and many other architectural marvels.

Lewes

Thanks to the Lewes Historical Society, Lewes offers a number of wonderful walking tours. The Lewes History Highlights Walking Tour begins at the Sussex Tavern building and walks through 300 years of Lewesian history. The Lewes Legends Evening Walking Tour is a 90-minute tour of legendary historical sites, including the Cannonball House Maritime Museum, where the British cannonball was lodged in its foundation during the War of 1812. But that wasn't Lewes' only naval conflict, as you'll learn when you explore the Historic Shipcarpenter Street Campus during the Revolutionary Lewes Walking Tour or climb a decommissioned military tower at Cape Henlopen State Park.

City of Delaware

Delaware City is a quaint settlement with convenient walking trails at the junction of the Delaware River and the canal. Attractions along the Delaware River include Fort Delaware State Park and Fort DuPont State Park, while along the Delaware City Branch Channel there are the Delaware City Marina, the African Union Church Cemetery, and Battery Park. The latter is the 2024 check-in point for Hike Across Delaware, an annual cross-state event we mentioned in the introduction. If all goes according to plan, participants will be bused from Battery Park to Chesapeake City, Maryland, on November 2, where they will embark on a 15-mile hike along the north side of the Chesapeake and Delaware Canal. Refreshments and restrooms will be offered in St. Georges about two-thirds of the way through. The hike ends back in Delaware City.

Milton

A small town with big attractions, you can easily walk a mile in Milton. The biggest is the Dogfish Head Milton Brewery, whose building is guarded by a 40-foot-tall “steampunk treehouse” that serves as a creative space for employees. Another great place to visit is the Milton Theater, built around 1910 and weathering fires and nor'easter storms to become Milton's entertainment center. The theater hosts plays, concerts, comedy shows, festivals and movies.

If you prefer to have a professional organize your walking tour, the Milton Historical Society offers regular architectural tours. Let them guide you past nearly 200 historic homes and commercial buildings in Milton's historic district.

Bethany Beach

Although not as large or famous as Rehoboth, Bethany Beach is a charming seaside community with its own beautiful boardwalk. BB's nearly half-mile long and 12-foot wide boardwalk offers ocean views, beach access and (fairly) large shops. A boardwalk-goer can't walk a few feet without being tempted by a smoothie at Turtle Beach Cafe, fries at Boardwalk Fries, cocktails at Mangos and a nap at Bethany Beach Ocean Suites Residence Inn. But the biggest temptation might be the Bandstand, which stands near the center of the boardwalk and hosts a wide variety of musical performances, especially during the Bethany Beach Seaside Concert Series. Cellofest, The Flying Ivories and the Hathway Brothers are just a few of the artists booked for the 2024 series. Let them and others be the soundtrack to a summer stroll through Bethany Beach.

Delaware: A treasure for hiking from coast to coast

Perhaps the only U.S. state that can be comfortably traversed on foot, Delaware is a pedestrian's paradise. In addition to the pedestrian-friendly wilderness, Delaware's cities are filled with parks, boardwalks, historic sites and shops that facilitate and direct foot traffic. Leave your car behind and lace up your sneakers for a trip to Rehoboth Beach, New Castle, Georgetown, Lewes, Delaware City, Milton and Bethany Beach.