12 Coolest Small Towns in New York for a Summer Vacation

The Skaneateles Festival opens its summer chamber-music season every August. The Old Rhinebeck Aerodrome runs WWI biplane airshows every Saturday and Sunday from May through October. The Hudson Valley Shakespeare Festival sets up its summer season on the Boscobel lawn outside Cold Spring. Watkins Glen State Park's gorge trail past 19 named waterfalls runs at peak flow in early July. The twelve New York small towns below each earn their place on a summer trip for specific reasons.

Lake Placid

Lake Placid sits at the heart of the Adirondacks. Mirror Lake, the small body of water in the village center, is the working summer water: kayaks, paddleboards, and rowing shells launch from the public beach, and a paved 2.7-mile path circles the shoreline. The 1980 Olympic venues are still in use; the Lake Placid Olympic Center hosts skating events year-round, and the bobsled and luge runs at Mount Van Hoevenberg run summer training and rides. Whiteface Mountain has a paved auto road to the summit (4,867 ft), and the surrounding High Peaks region of the Adirondack Mountains has 46 peaks over 4,000 feet for the more ambitious hikers.

Cold Spring

Cold Spring sits on the east bank of the Hudson River, directly across from West Point. Main Street runs downhill from the Metro-North station to a small waterfront with antique shops, art galleries, and restaurants between. Hudson Highlands State Park starts at the village edge: the Breakneck Ridge trail (one of the more demanding short hikes in the eastern US) and the gentler Bull Hill loop both leave from town. Boscobel House and Gardens, a restored neoclassical mansion two miles north, runs garden tours and the summer Hudson Valley Shakespeare Festival on the lawn. The Metro-North Hudson Line makes the village a 75-minute train ride from Grand Central.

Skaneateles

Skaneateles is a village on the north end of Skaneateles Lake, one of the Finger Lakes, and one of the cleanest large lakes in the United States (the village water supply is unfiltered surface water from the lake itself). Mid-Lakes Navigation runs lunch and dinner cruises from the pier on the Judge Ben Wiles. Anyela's Vineyards and several smaller wineries spread along the lake's western shore. The Skaneateles Festival, a chamber-music event running annually since 1980, brings concerts to a barn on Brook Farm and several other venues across August.

Aurora

Aurora is a small village on the eastern shore of Cayuga Lake, the longest of the Finger Lakes. The lake-facing strip of town runs less than a mile and contains Wells College, the Aurora Inn, the MacKenzie-Childs flagship store and farm (the home-goods company is headquartered here, and the painted Victorian farmhouse on a hill above the lake is open to visitors), and a few restaurants. Long Point Winery and Bet the Farm Winery are short drives away. Long Point State Park has lake-access hiking, and the Montezuma National Wildlife Refuge at the lake's north end is a major stop on the Atlantic Flyway for waterfowl in spring and fall.

Woodstock

Woodstock, in the eastern Catskills, was a working artists' colony decades before the 1969 music festival (which actually happened 60 miles southwest in Bethel, not here). The Byrdcliffe Arts Colony, founded in 1902, is still in operation and is one of the oldest continuously running arts colonies in the country. The Center for Photography at Woodstock and several galleries on Tinker Street round out the working art scene. For the festival history, Bethel Woods Center for the Arts sits on the original 1969 site and runs a museum, an outdoor amphitheater, and concert programming from late spring through fall. The Catskill Forest Preserve borders Woodstock, and the Ashokan Reservoir's promenade runs along the village's southern edge.

Cooperstown

Cooperstown sits on the southern tip of Otsego Lake, with the National Baseball Hall of Fame and Museum on Main Street as the obvious draw. The Fenimore Art Museum (named for novelist James Fenimore Cooper, who set The Leatherstocking Tales here) holds a strong collection of American folk art and a major collection of Native American material on the lake's western shore. Glimmerglass State Park covers the lake's north end with swimming and hiking. Brewery Ommegang, a Belgian-style brewery on the south side of town, runs tastings, tours, and a summer concert series. The town swells dramatically during Hall of Fame Induction Weekend in late July; visit on a different week for breathing room.

Greenport

Greenport is a working harbor village on the North Fork of Long Island, two and a half hours from Manhattan by car or three by train. Unlike the South Fork (the Hamptons), the North Fork is mostly working farmland and vineyards, and Greenport sits at its end. The harbor still has a commercial scallop and oyster fleet, the East End Seaport Museum, and a restored 1920s carousel in Mitchell Park. Orient Beach State Park covers the easternmost point. Local wineries include Kontokosta and One Woman Wines & Vineyards. Shelter Island, accessible by a five-minute ferry from the foot of Greenport, has Mashomack Preserve (about 2,100 acres of Nature Conservancy land with hiking trails along salt marshes and coves).

Lewiston

Lewiston sits on the lower Niagara River seven miles downstream of the falls, on the American side. The Freedom Crossing Monument on the riverfront marks the village's role as a crossing point on the Underground Railroad before the Civil War. Center Street is the village's commercial spine, lined with restaurants and small shops. Artpark, a 150-acre state park on a riverside ridge, runs an outdoor amphitheater concert series each summer. Niagara Jet Adventures runs whitewater jet boat trips through the Devil's Hole rapids in the Niagara Gorge from the village dock.

Watkins Glen

Watkins Glen sits at the southern tip of Seneca Lake, the deepest of the Finger Lakes. The headline attraction is Watkins Glen State Park: a stone gorge with 19 named waterfalls along a 1.5-mile gorge trail that climbs through tunnels carved into the rock and behind several of the falls. The Seneca Lake Wine Trail, with around 30 wineries (Castel Grisch, Lakewood Vineyards, Hermann J. Wiemer, and others) wraps the lake. Watkins Glen International, four miles north of town, hosts a NASCAR Cup Series race each August and several other professional racing events through the summer.

Rhinebeck

Rhinebeck is a Hudson Valley village on the east side of the river, north of Poughkeepsie. The Dutchess County Fairgrounds host the Dutchess County Fair every August (the second-largest agricultural fair in the state) and dozens of other events through the year. The Old Rhinebeck Aerodrome, four miles north, runs weekend airshows of pre-WWII aircraft from May through October. The Vanderbilt Mansion National Historic Site (a Gilded Age estate on 211 acres) and the Staatsburgh State Historic Site (a Beaux-Arts mansion) are both ten minutes from the village center. The Beekman Arms, in operation since 1766, claims to be the oldest continuously operating inn in the United States.

Saranac Lake

Saranac Lake sits ten miles west of Lake Placid in the Adirondack Park. The town was the country's leading tuberculosis treatment center from the 1880s until streptomycin made the cure mostly obsolete in the 1950s; the Saranac Laboratory Museum (Trudeau Institute's original lab) covers that history. The Saranac Lake chain of lakes connects directly to the Saranac River and on through the Raquette River system, giving canoeists and kayakers access to a multi-day paddling network. Galleries on Broadway include the Adirondack Artists' Guild and BluSeed Studios. The Saranac Lake Winter Carnival in early February draws large crowds, but the rest of the year the town is a quieter alternative to its neighbor.

Sleepy Hollow

Sleepy Hollow, on the east bank of the Hudson 30 miles north of Manhattan, is the village Washington Irving fictionalized in The Legend of Sleepy Hollow. Sleepy Hollow Cemetery contains his grave alongside Andrew Carnegie, Walter Chrysler, and several other industrialists. Philipsburg Manor (a restored 1750 manor and gristmill) and Kykuit (the Rockefeller family estate) sit nearby. Rockefeller State Park Preserve covers about 1,800 acres east of the village with 55 miles of carriage roads converted to walking and horseback riding paths. The town's October pumpkin and Halloween programming (the Great Jack O'Lantern Blaze, Horseman's Hollow at Philipsburg Manor) is famous, but July and August are quieter and the river views are at their best.

The twelve summer trips above are not interchangeable. The Adirondack water-and-mountain pairings of Lake Placid and Saranac Lake are a different proposition than the Hudson estate days of Rhinebeck or the Finger Lakes wineries around Aurora and Skaneateles. Pick two or three for a long weekend; the rest will still be there next summer.