Nearest City: New York, 103 miles
There's no such thing as a straightforward stroll down Millerton's Main Street, even if it is only a couple of blocks long. Inevitably, you're tempted to pop into one shop, zigzag over to another, or grab a latte and a scone at Irving Farm Coffee House, an offshoot of a Manhattan café (44 Main St., 518/789-6540, irvingfarm.com). The Dutchess County village lies within 30 minutes of prime second-home destinations, yet Millerton has remained affordable and unpretentious. "This town feels very real," says Susan Schneider, who moved her business, Shandell's, which sells vintage and new lamps, from Connecticut to Millerton in 2004 (34 Main St., 518/789-6603, shandells.com). In 2005, Robin Helfand, a former manager of New York City's Dean & Deluca, opened a specialty food store, Millerton Market (21 Main St., 518/789-6677), and this past spring she launched another enterprise, Millerton Card & Candy Co. (28 Main St., 518/789-8669). Helfand credits Millerton's growing appeal to its old-fashioned Main Street: "It's full of independent businesses instead of chain stores," she says, "so you see products that reflect what the community really wants."