14 Best Small Towns To Visit In New York
Saranac Lake holds an ice palace built from blocks cut out of Lake Flower every February. Cooperstown houses the Baseball Hall of Fame on a working Main Street that predates the game by a century. Sleepy Hollow gave Washington Irving his Headless Horseman and still names its bridges after the legend. Greenport caps off the North Fork's wine country with a working 1920s carousel. New York State is enormous, and these 14 small towns make the case for getting out and seeing it.
Greenport
Greenport sits on Long Island's North Fork, the eastern tip best known for vineyards and quieter waterfront than the Hamptons across Peconic Bay. Mitchell Park has the original 1920s Greenport carousel, restored and operating, plus a small harbor green. The East End Seaport Museum at the foot of Front Street covers North Fork maritime history. Front Street and Main Street downtown hold independent shops, art galleries, and casual seafood spots. The town serves as the eastern terminus of the Long Island Rail Road and connects by ferry to Shelter Island.
Saranac Lake
Saranac Lake sits in the heart of the Adirondacks. The town was a major tuberculosis treatment center in the late 19th and early 20th centuries (cure cottages from that era still line the streets), and writer Robert Louis Stevenson lived here while seeking treatment in the winter of 1887-88. His cottage is now the Robert Louis Stevenson Museum. The Saranac Lake area has dozens of lakes for canoeing, kayaking, and fishing, and the High Peaks region is just south. The annual Saranac Lake Winter Carnival, running since 1897, builds an ice palace from blocks cut out of Lake Flower each February.
Skaneateles
Skaneateles (pronounced "skinny-AT-las") sits at the northern end of Skaneateles Lake, one of the easternmost of the major Finger Lakes. The lake is also one of the cleanest in the country and supplies drinking water without filtration. Downtown Skaneateles holds Victorian-era buildings, restaurants, and lakefront access at Clift Park, where a small gazebo and the historic Skaneateles Pier mark the village center. Mid-Lakes Navigation runs lake cruises in season. The Skaneateles Festival each August stages chamber music in venues around town.
Woodstock
Woodstock in the Catskill Mountains has a long arts and counterculture history that predates the famous 1969 music festival. The festival itself wasn't actually held in Woodstock; it took place on a dairy farm in Bethel, about 60 miles southwest. The town has been a magnet for artists since the founding of the Byrdcliffe Colony in 1902, the country's longest continuously operating arts and crafts colony. The Woodstock Artists Association & Museum displays work from the area's deep artistic roots. Tinker Street is the main commercial strip with bookstores, music shops, and cafes. Kaaterskill Falls (one of the highest waterfalls in New York at 260 feet across two tiers) is a short drive northwest in nearby Haines Falls.
Cooperstown
Cooperstown on Otsego Lake is best known for the National Baseball Hall of Fame and Museum, but the town predates baseball by a century. James Fenimore Cooper (yes, that Cooper, author of The Last of the Mohicans) grew up here, and the town is named for his father William, who founded it in 1786. The Fenimore Art Museum and the Farmers' Museum sit just north of town and cover regional art and 19th-century rural life. The Glimmerglass Festival each summer stages opera and musical theater at the Alice Busch Opera Theater on the lake. Main Street holds restaurants, vintage shops, and Cooperstown's distinctive baseball memorabilia stores.
Trumansburg
Trumansburg sits in the heart of the Finger Lakes wine region. Taughannock Falls State Park just south of town holds Taughannock Falls, at 215 feet one of the highest single-drop waterfalls east of the Mississippi and 33 feet taller than Niagara Falls. The Trumansburg Fairgrounds host the annual Trumansburg Fair each August with rides, livestock displays, and live music. The Grassroots Festival, also held in town each July, draws thousands for four days of music. Main Street holds shops housed in 19th-century Greek Revival buildings.
New Paltz
New Paltz, home to a SUNY campus, sits in the Shawangunk Mountains in the Mid-Hudson Valley. The Mohonk Preserve covers 8,000 acres of cliffs, forest, and lakes for hiking, rock climbing, and cycling. Adjacent Mohonk Mountain House (a 19th-century resort built in 1869) is one of the largest still-operating Victorian-era hotels in the country, set on its own 1,300-acre estate. Historic Huguenot Street preserves seven stone houses from the late 17th century and is the oldest authenticated street with original homes in America. Downtown New Paltz holds the typical mix of student-friendly cafes, shops, and farm-to-table restaurants.
Cold Spring
Cold Spring on the Hudson River is one of the most popular weekend escapes in the Hudson Valley, reachable in about 75 minutes by Metro-North. Main Street drops down to the river through a 19th-century commercial district lined with antique stores, cafes, and small galleries. The Foundry Dock Park sits at the river's edge with views of Storm King Mountain across the water. Hudson Highlands State Park has the famous Breakneck Ridge Trail, one of the toughest day hikes in the region. The West Point Foundry Preserve a few minutes south covers the ruins of a major 19th-century cannon foundry that supplied Union forces during the Civil War.
Rhinebeck
Rhinebeck in the Mid-Hudson Valley centers on the Beekman Arms, established in 1766 and one of the oldest continuously operating inns in the country. The Old Rhinebeck Aerodrome north of town flies vintage aircraft from the dawn of aviation through the 1930s in weekend airshows from June through October. The Dutchess County Fair is the second-largest county fair in New York and runs in late August. Ferncliff Forest provides hiking trails just outside town, and the Hudson River sits five miles west. Restaurants like Gigi Trattoria and Aroi Thai have made Rhinebeck a regional dining destination.
Sleepy Hollow
Sleepy Hollow takes its name and identity from Washington Irving's 1820 short story "The Legend of Sleepy Hollow." Visitors can walk the old Headless Horseman Bridge replacement on Bedford Road and tour Sleepy Hollow Cemetery, where Irving himself is buried. The Great Jack O'Lantern Blaze is an annual fall event held at Van Cortlandt Manor in nearby Croton-on-Hudson, with more than 7,000 hand-carved jack o'lanterns drawing crowds from across the country. The Sleepy Hollow Lighthouse on the Hudson dates to 1883. Kykuit, the former Rockefeller family estate, offers tours of its mansion, gardens, and modern art collection.
Kingston
Kingston served as New York State's first capital in 1777, before British troops burned it later that year. The Stockade District in uptown Kingston still preserves the colonial-era street grid and several pre-Revolutionary stone houses. The Senate House State Historic Site is where the New York State Senate first met. The Rondout District on the Hudson River, once a major shipping port for Catskills bluestone and cement, has been redeveloped with the Hudson River Maritime Museum, restaurants, and a tourist train aboard the Catskill Mountain Railroad. The Forsyth Nature Center north of downtown maintains a free zoo with rescued and donated animals.
Lake Placid
Lake Placid hosted the Winter Olympics in 1932 and 1980, and the venues are still in active use for training and competition. The Olympic Center on Main Street holds the original 1932 indoor arena and the Herb Brooks Arena, where the U.S. men's hockey team's "Miracle on Ice" upset of the Soviet Union took place in 1980. The Olympic Sports Complex on Mount Van Hoevenberg has bobsled, luge, skeleton, and biathlon facilities open to visitors. Lake Placid sits between Mirror Lake (downtown, walkable) and the larger Lake Placid (just north of town). Whiteface Mountain a few miles east in Wilmington is one of the largest ski areas in the East and was the alpine venue for both Olympics.
Saugerties
Saugerties sits on the Hudson River where Esopus Creek meets the river, with the Saugerties Lighthouse (1869, restored and now operating as a B&B) at the river entrance. Main Street holds art galleries, vintage shops, and cafes. Opus 40 a few miles southwest is a 6.5-acre sculpture park hand-built over 37 years by sculptor Harvey Fite from the bluestone of an abandoned quarry. The HITS Saugerties horse show grounds host major equestrian competitions through the summer. Krause's Chocolates, the local Saugerties flagship, sells handmade chocolates from a 1929 recipe.
Beacon
Beacon on the Hudson River has reinvented itself from a 19th-century factory town into a contemporary art destination. The Dia:Beacon, set in a 300,000-square-foot former Nabisco printing factory, holds large-scale works by Andy Warhol, Donald Judd, Richard Serra, and others. Main Street stretches more than a mile through restaurants, galleries, and music venues. Mount Beacon offers a steep climb with views of West Point and the Hudson Highlands. Long Dock Park on the river has a sandy beach, kayak rentals, and the Pete Seeger Riverfront Park stage. Pollepel Island in the river holds the ruins of Bannerman Castle, accessible by boat tour from May through October.
Where New York Opens Up
Greenport's North Fork harbor, the Adirondack peaks around Lake Placid, the antiques and stone houses of New Paltz. These 14 towns each pull on something different. A baseball Hall of Fame, an Olympic arena, a 19th-century arts colony, a Victorian inn pouring drinks since the Continental Congress. New York stretches a long way past any one impression of it.
