7 of the Most Walkable Towns in Delaware

Even at its widest point, Delaware can be walked in a day. At its narrowest point, it can be walked in a few hours. People walk across Delaware so regularly, in fact, that there is an annual event called Hike Across Delaware, where dozens of hikers come for a non-competitive crossing of a 15-mile stretch of the state. But you do not have to walk that far for a trampling sampling of Delaware. Its small towns have pedestrian-friendly paths lined with historic, commercial, and natural attractions that host leisurely walking tours. 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 walkable. Rehoboth Beach's boardwalk is about a mile long and flanked on one side by the titular beach and flanked on the other by bustling businesses. These include Zelky's Beach Arcade, Funland, and the Rehoboth Toy & Kite Company. Rehoboth's walkability extends far beyond the boardwalk, though. Its side streets are lined with elegant eateries like Theo's Steaks, Sides & Spirits, and Aroma Mediterranean Cuisine, both of which have been stops on the Sunday Eating Rehoboth Walking Food Tour. Fans of history 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. It is a granite remnant of a much tamer Rehoboth.

New Castle

As one of the oldest communities in Delaware, New Castle's attractions have existed for centuries. Virtually all of them occupy the New Castle Historic District, which covers several blocks in the center of town and contains hundreds of historic buildings. Various guided and self-guided walking tours teach visitors about the district and highlight its grandest structures, such as the New Castle Court House (c. 1732), Amstel House (c. 1738), Dutch House (c. 1690), Read House & Gardens (c. 1804), and Old Town Hall (c. 1823). There is even an Audiowalk that pairs informative clips with a tour of 46 different sites.

Georgetown

You will go in circles in Georgetown, but that is by design, not insanity. This 7,000ish-person town was laid out in a circular pattern. Naturally, one should start their tour of Georgetown inside the Circle, which was designed in the 1790s and is now a verdant park with a picturesque fountain. From there, all one has to do is walk around the Circle for a centuries-spanning survey of Georgetown architecture. Striking historic buildings include the New Sussex County Courthouse (c. 1840) and Brick Hotel (c. 1836).Not all of Georgetown's buildings are confined to the Circle, however. Skirting its straight streets are the Old Sussex County Courthouse (c. 1792), St. Paul's Episcopal Church (c. 1844), and many other architectural marvels.

Lewes

Thanks to the Lewes Historical Society, Lewes hosts an array of wonderful walking tours. The Lewes History Highlights Walking Tour embarks from the Sussex Tavern building and retraces 300 years of Lewesian steps. The Lewes Legends Evening Walking Tour is a 90-minute survey of legendary historic sites, including the Cannonball House Maritime Museum, which displays the British cannonball lodged in its foundation during the War of 1812. But that was not Lewes' only maritime conflict, as you will learn while exploring the Historic Shipcarpenter Street Campus during the Revolutionary Lewes Walking Tour or while climbing a defunct military tower in Cape Henlopen State Park.

Delaware City

Delaware City is a scenic settlement with easy walking paths at the intersection of the Delaware River and the canal. Sites to see along the Delaware River include Fort Delaware State Park and Fort DuPont State Park, while features to find along the Delaware City Branch Channel include the Delaware City Marina, African Union Church Cemetery, and Battery Park. The last of those is the 2024 check-in point for Hike Across Delaware, an annual state-crossing event that we mentioned in the intro. If all goes as planned, participants will be bussed on November 2 from Battery Park to Chesapeake City, Maryland, where they will embark on a 15-mile hike along the north side of the Chesapeake and Delaware Canal. Refreshments and restrooms are offered in St. Georges about two-thirds of the way through. The hike concludes back in Delaware City.

Milton

It is easy to walk a mile in Milton, which is a small town with big attractions. The biggest is Dogfish Head Milton Brewery, whose building is guarded by a 40-foot "Steampunk Treehouse" that is a creative space for staff. Another prodigious place to peep is the Milton Theatre, which was built circa 1910 and survived fires and nor’easters to become the entertainment hub of Milton. Plays, concerts, comedy shows, festivals, and films can all be seen at the theater.

If you prefer a professional to organize your on-foot expedition, the Milton Historical Society provides periodic architectural tours. Get led past nearly 200 historic homes and commercial haunts in the Milton Historic District.

Bethany Beach

Though not as large or famous as Rehoboth, Bethany Beach is a charming coastal community with its own beautiful boardwalk. Almost half a mile long and 12 feet wide, BB's boardwalk offers ocean views, beach access, and big(ish) business. A boardwalker cannot go a few feet without being tempted by a smoothie at the Turtle Beach Cafe, fries at Boardwalk Fries, cocktails at Mangos, and a nap at the Bethany Beach Ocean Suites Residence Inn. But the strongest temptation might be the Bandstand, which stands near the center of the boardwalk and hosts a wide variety of musical acts, especially during the Bethany Beach Seaside Concert Series. Cellofest, The Flying Ivories, and the Hathway Brothers are just some of the artists that were booked for the 2024 series. Let them and others be the soundtrack to a summer stroll through Bethany Beach.

Delaware: A Walkable Treasure from Shore to Shore

As probably the only US state that you can leisurely walk across, Delaware is a pedestrian's paradise. Beyond its walkable wilderness, Delaware's towns are filled with parks, boardwalks, historic sites, and businesses that facilitate and filter foot traffic. Ditch your car and lace up your sneakers for a trip through Rehoboth Beach, New Castle, Georgetown, Lewes, Delaware City, Milton, and Bethany Beach.