Greenport: This is the cutest town on Long Island's North Fork. Filled with Colonial buildings, inns, homes, and shops, the town sits right on the protected waters of Peconic Bay. There's a strong sense of the town's history as a fishing village, with the smell of salt in the air, but there are also nice galleries and restaurants that line Main Street.
Cold Spring: Perhaps the most visitor-friendly small town on the Hudson, warm and inviting Cold Spring has something for everyone. The historic waterfront, equipped with a Victorian band shell and park benches, has unequaled views of the Hudson River; Main Street is packed with antiques shops, cafes, and restaurants; and the nearby mountains are perfect for surprisingly rigorous hikes. Cold Spring is within easy reach of lots of historic estates along the river, and the town's excellent handful of restaurants and inns could easily entice you to a much longer stay than you had planned.
Aurora: A tiny, picture-perfect village hugging the east shore of Cayuga Lake, Aurora, now in the throes of full-scale revitalization, could be a movie set. It pretty much consists of a main street, a village market, a pizza restaurant, an ice-cream parlor, a historic inn, a whimsical ceramics factory, and a women's college. The town owes its startling makeover to the efforts of the Aurora Foundation, set up by a single benefactor who made it big with American Girl dolls and set about overseeing the restoration of the village's historic buildings, including the beautiful 1833 Aurora Inn (like the town, on the National Register of Historic Places). Visiting the campus of ceramics maker MacKenzie-Childs is about as close to a Willy Wonka wonderland as you'll get.
Cooperstown: This chain-store-free town is best known for being home to the Baseball Hall of Fame. But sitting on the shores of Lake Otsego, it's also one of the state's cutest small towns. Tiny buildings and shops line the short Main Street, and you can walk its length in just a few minutes. You'll find quaint inns, good restaurants, and plenty of baseball-card shops; then walk down to the water and have a picnic lunch overlooking the quiet, undeveloped lake.
Skaneateles: They don't come any cuter (or harder to pronounce) than this graceful town, which is more reminiscent of New England than upstate New York. The historic downtown, an attractive mix of 19th-century Greek Revival and Victorian homes and appetizing boutiques and antiques shops lining East Genesee Street, sits right on the north shore of Skaneateles Lake. The beautiful and crystal-clear lake is one of the prettiest and cleanest in the state, and charming inns and restaurants back right up to it. In summer, bands play on the lakefront at a picturesque gazebo, and in winter, costumed actors create a Dickensian holiday.
Saranac Lake: Less hectic than its neighbor, Lake Placid, this town boasts a charm all its own. With tiny clapboard shops mixed in with cute brick structures, the town has a couple of good restaurants, along with a pretty inn and clean streets.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.