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Jackson, Wyoming
Unlike most Wild West towns, it’s got a bustling commercial airport. A 15-minute taxi ride through Jackson’s picturesque outskirts will bring you from JAC to the town square, where dozens of hotels sit within walking distance. Stay at the luxurious Cloudveil or the affordable-but-trendy Anvil Hotel to be steps from all the action. When you’re ready to take in the surrounding Teton Range, rent a bike or book an excursion — outfitters like Jackson Hole Wildlife Safaris can come right to your hotel doorstep to pick you up for a private or group tour.
Traverse City, Michigan
Michigan’s most famous pedestrian hotspot is Mackinac Island, which has forbidden cars since 1898. Insiders know, though, that the island is near-impossible to reach without first driving to the mainland’s far-flung ferry ports. For an easier experience, travel instead to Traverse City, two hours south. This charming town of 15,000 comes with its own airport, as well as a walkable, beachfront downtown that’s loaded with fudge shops, boutiques, and stylish lodgings. TC is also an outdoor lover’s paradise, offering everything from kayaking on Grand Traverse Bay to hiking and biking on the TART Trails network, which crisscrosses almost all of the Leelanau Peninsula.
Laurel, Mississippi
Laurel, Mississippi, located 90 miles southeast of Jackson. The town of 17,000 has gained national attention as the setting of HGTV’s Home Town, but the architecture and shops created by the show’s Erin and Ben Napier aren’t the only things to see here. From the city’s many downtown Airbnbs, you can walk to a world-class art museum and a park designed by the firm of Central Park architect Frederick Law Olmsted. Laurel also boasts a downtown Amtrak station, making it an easy rail destination — particularly from New Orleans, a three-hour ride away.
Red Wing, Minnesota
Lying just southeast of the Twin Cities, the Mississippi River town of Red Wing has shopping, historic hotels (try the St. James), and a wealth of hiking, biking, and fishing opportunities. Not arriving by boat? Red Wing also lies on Amtrak’s new Borealis line connecting Chicago and St. Paul.
Carmel-by-the-Sea, California
California’s Central Coast is world-famous for its scenic driving, but it’s just as stunning to explore on foot. The storybook town of Carmel especially prizes walkability, with a one-square-mile downtown that’s laced with pedestrian-only lanes. Take a stroll along the beach before tucking in for dinner at the Michelin-starred Chez Noir and an overnight at L’Auberge Carmel. The Monterey Regional Airport is a 10-minute Uber ride away, making Carmel easy to fly into, but ambitious hikers and cyclists can also access the town via the California Coastal Trail, a statewide network that includes 144 miles of trails here in Monterey County.
Rosemary Beach, Florida
So getting to this teensy Panhandle village requires some effort — it’s a 30-minute drive from the airport in Panama City. Once you’re here, though, you’ll see why it’s worth the extra-long Uber. Rosemary Beach was built from scratch in 1995 with a walkable, New Urbanist master plan, and its 105 acres are explorable entirely by foot, bicycle, or golf cart. Stay in one of the town’s plentiful luxury vacation rentals, and you’ll be strolling distance from exceptional spas, lively restaurants, and some of the country’s greatest white-sand beaches.
