Nearest City: Albany, 35 miles
Thomas Cole, founder of the Hudson River School of landscape painting, was so enamored with the area that he moved to Catskill in the 1830s—his former home and studio is now the Thomas Cole National Historic Site (218 Spring St., 518/943-7465, thomascole.org, $7).
After a period of neglect in the 1980s and '90s, Catskill is attracting artists again, as much for its affordable Victorian homes as for the surroundings. In 2005, musician Frank Cuthbert turned a crumbling 19th-century building into the Brik Gallery, which hosts exhibits as well as classical-music concerts and readings (473 Main St., 518/943-0145, brikgallery.com). Down the street, Argentine artist Dina Bursztyn and her partner, Julie Chase, display their works—some made from river driftwood—at their three-year-old gallery, Open Studio (402 Main St., 518/943-9531, potatospirit.com). Another foreign transplant, Israel-born Yael Manor-McMorrow, and her husband, Keith McMorrow, cook an excellent brunch at Bell's Café-Bistro (387 Main St., 518/943-4070, bellscafeny.net, omelet $9).
Catskill's diversity is part of what inspired David Miles to move here to set up his furnishings store, Hood & Company (432 Main St., 518/943-1891, hoodandcompany.com). Well, the town's architecture certainly played a role, too. "When I first turned on Main Street, I fell in love," he says.
> See photos of the coolest small towns
> See available real estate in the coolest small towns