12 Unforgettable Small Towns to Visit in New York
The downtown sidewalks in Chittenango are paved in actual yellow brick, and there is a good reason for it: the town is the birthplace of L. Frank Baum, the man who wrote The Wonderful Wizard of Oz, so it built a whole identity around the road to the Emerald City. That kind of full commitment to a single strange idea is what makes a small town stick. New York has a surprising number of them. Geneseo kept an entire Victorian main street so intact that the whole downtown landed on the National Register, while others stake everything on a deep glacial lake, a summer racetrack, or a waterfall that beats Niagara on sheer height. The thread running through all of them is the same: none of these places blends in, and not one of them wants to.
Camillus
The standout in this village west of Syracuse is a piece of Erie Canal history you can walk across. The restored Nine Mile Creek Aqueduct at Camillus Erie Canal Park carries the old towpath over the water on a timber-and-stone span, one of the few navigable aqueducts left from the original canal. Come winter, the same path turns into a cross-country ski trail.
Sims' Store Museum, a rebuilt 1856 canal store, sits at the park entrance with a small fleet of boats out front. Federal-style houses fill the blocks between the canal and Main Street, and Three Rivers Wildlife Management Area is a few miles up the road for anyone who wants a longer day in the woods.
Chittenango
L. Frank Baum was born here in 1856, and the town has never once played it cool about it. The downtown sidewalks are paved in actual yellow brick, which is the kind of full commitment most places talk themselves out of. The All Things Oz Museum keeps the memorabilia, and early every June, Oz-Stravaganza fills Main Street with a parade and costume contests.
The off-theme hours are covered too, by the Yellow Brick Road Casino and the Chittenango Landing Canal Boat Museum. Just south of town, Chittenango Falls State Park drops a wide curtain of water over a wall of stair-stepped limestone, with a trail that switchbacks down to the base for the view looking up.
Geneseo
The whole of downtown Geneseo sits on the National Register of Historic Places, Victorian storefronts running the length of Main Street with almost nothing out of period. The Wadsworth Library occupies the old Wadsworth family home, and come December, the Charles Dickens Christmas weekend turns the street into an open-air Victorian set with characters strolling in period dress.
The bigger draw is fifteen minutes west at Letchworth State Park, where the Genesee River has carved a gorge with cliffs reaching some 600 feet. The nickname there, the "Grand Canyon of the East," gets used a lot, and for once it earns it.
Geneva
Geneva anchors the northern end of Seneca Lake, the deepest of the Finger Lakes, and the downtown revival here was real enough to earn the small city an All-America City award in 2015. Every weekend night through the season, Linden Street closes to cars and opens up its run of farm-to-table restaurants, breweries, and wine bars.
The lake handles the boaters, anglers, and swimmers all summer, and Hobart and William Smith Colleges hold down the south end, which keeps something on the calendar long after the tourist season winds down. It is a college town and a wine town that never quite decided to pick one.
Montauk
Montauk closes out the eastern tip of Long Island, and the Montauk Point Lighthouse is the image that sticks: first lit in 1796 under a commission signed by George Washington, still working, with a small museum at the base. The whole town runs a few notches slower than the rest of the South Fork, which is why everyone out here just calls it "The End."
Ditch Plains is the surf beach the regulars send you to first. When the mood calls for the upscale version of all this, Gurney's puts a full resort and spa right up against the ocean, but the appeal of Montauk has always been that it never tried as hard as the Hamptons to the west.
Pawling
Here is a trick almost nobody uses: you can ride a Metro-North train straight to the Appalachian Trail, because the line stops in Pawling and the trail walks right through town. There is even a dedicated AT platform a bit north, the only train stop on the entire 2,000-mile trail.
Dutcher Golf Course, which Golf Digest has called the oldest nine-hole municipal course in the country, has been in play since 1890, with original stone farm walls still cutting across the fairways. A handful of lakes sit within town limits, and hundreds of acres of public land open up at the Great Swamp and Nuclear Lake, a former research site with a name far spookier than the quiet pond it actually describes.
Saratoga Springs
Saratoga Springs is built on water that comes out of the ground already carbonated, which is a genuinely strange thing for a place to be famous for and exactly why it works. The mineral springs that named the town still bubble up through Saratoga Spa State Park, a National Historic Landmark of more than 2,200 acres, where the Roosevelt Baths still run mineral-water soaks across dozens of treatment rooms.
The same grounds host the Saratoga Performing Arts Center for summer concerts and ballet. Then there is the racetrack, one of the oldest in the country, which opens its meet in July and runs through Labor Day and effectively becomes the town's heartbeat for six weeks. Broadway downtown carries the rest, Victorian-era hotels still open along the stretch.
Skaneateles
Skaneateles sits at the foot of a lake so clean that Syracuse drinks straight from it without filtering, one of only a handful of unfiltered municipal water supplies in the country. That fact alone tells you most of what you need to know about the water at the bottom of Genesee Street.
Clift Park frames that water with a gazebo, a small beach, and benches that draw a crowd by mid-July. The Sherwood Inn has been putting up guests since 1807, when stagecoach magnate Isaac Sherwood built it, and still pours in the tavern downstairs. Come winter, the kayaks give way to ice skates and the occasional sleigh ride.
Sleepy Hollow
Sleepy Hollow leans all the way into its source material, and honestly, what else would it do. Washington Irving published "The Legend of Sleepy Hollow" in 1820 and now lies in Sleepy Hollow Cemetery, which adjoins the Old Dutch Church and the bridge from the tale. The village even changed its name from North Tarrytown to Sleepy Hollow in 1996 to make the connection official.
Every fall the whole place turns over to Halloween. Horseman's Hollow makes a haunted trail out of Philipsburg Manor, and the nearby Great Jack O'Lantern Blaze lights tens of thousands of carved pumpkins at Van Cortlandt Manor in Croton-on-Hudson. Kykuit, the Rockefeller estate just outside the village, runs house and garden tours, and the train from Manhattan takes about forty minutes.
Speculator
Speculator is the kind of Adirondack town where the lake and the trails do all the talking. Lake Pleasant fronts the village and handles the swimming, paddling, and fishing through the warm months, and when the snow arrives, hundreds of miles of groomed snowmobile trail radiate out of the area.
Charlie John's Grocery pulls triple duty as a hardware store, a souvenir shop, and the place to grab a topographic map before you head out. Oak Mountain Ski Center up the road handles the downhill at a family scale, and the hike out to Kunjamuk Cave is the off-the-map errand that pays off for anyone willing to find it.
Trumansburg
Trumansburg's headline act is a waterfall taller than Niagara. Taughannock Falls drops 215 feet in a single plunge inside Taughannock Falls State Park, on the western edge of Cayuga Lake, which makes it 33 feet higher than Niagara and the tallest single-drop waterfall east of the Rockies.
The Inn at Taughannock perches above the gorge with a restaurant on the property, and the town's own Main Street holds a tidy lineup of farm-to-table cafes, vintage shops, and bed-and-breakfasts. Every July, the GrassRoots Festival of Music and Dance pulls dozens of bands into town for four days and roughly quadruples the population while it lasts.
Towns That Stick With You
The towns that stay with you tend to have one obsession they wear right out in the open. Skaneateles built a village around water clean enough to drink straight from the lake. Saratoga Springs lives on water that fizzes out of the ground on its own. Speculator measures its winters in miles of snowmobile trail, and Pawling guards a golf course older than most of the cars parked beside it. The trick is that none of these places is far away. Pick the one nearest home, give it an afternoon, and the corner of New York you thought you already knew starts looking a good deal stranger and better.
