20. Maryland: Frostburg
Within the Allegheny mountains, you’ll find this jumping-off point of the Great Allegheny Passage. It attracts outdoorsy and mountain types year-round. You’ll find classic small-town eateries on its brick-lined downtown streets. They lead to a trailhead that branches to Cumberland in one direction, and Pittsburgh in the other. Hop on the Western Maryland Scenic Railroad for sightseeing and comfort.
21. Massachusetts: Stockbridge
If this town feels like a Norman Rockwell painting, it’s because much of his work was inspired by Stockbridge. The town is the home of the Norman Rockwell Museum. You’ll find a large collection of historic homes and museums, including the Clark Art Institute. In winter, the town transforms into a Christmas wonderland and another classic image of Americana.
22. Michigan: Traverse City
Bordered by the Grand Traverse Bay of Lake Michigan, it’s the gateway to nature and the Sleeping Bear Dunes National Lakeshore. A trail of 40 wineries sits just outside the city, and Leelanau Peninsula is one of the most underrated wine regions in the world. There’s something for every season here, with skiing at the Crystal Mountain Resort.
23. Minnesota: Grand Marais
Located off one of America’s most scenic drives, Highway 61 on Minnesota’s North Shore, and 40 miles from Canada, it’s a must-stop. Its Scandinavian heritage is evident everywhere. You’ll find some of the state’s best pizza, as well as other cool ethnic eateries downtown. Visit some of the local breweries, or satisfy your sweet tooth with ice cream or doughnuts.
24. Mississippi: Ocean Springs
Located just east of Biloxi, rests this artsy village and beach destination with beautiful white sand. Stay at the floating cabins at the Beatnik Hotel. There’s an open container district where you can bar hop along Government Street and take in several live bands in one night. Good food and art are abundant. Visit the Walter Anderson Museum of Art.
