11 Of The Most Adorable Small Towns In Upstate New York
19th-century buildings that line tiny villages in the Finger Lakes, tie-dye t-shirt shops in the Catskill Mountain town of Woodstock, and authentic 1950s bowling alleys in Trumansburg are just part of what makes these towns in upstate New York so adorable. Cold Spring's historic district and Skaneateles' charming array of locally organized annual festivals also help drive visitors to this part of the country. Since Upstate New York, roughly defined as the region north of the greater New York City area, spans a diverse landscape that includes the Adirondacks, these communities are also surrounded by natural beauty. Whether in Saranac Lake, Beacon, or Schroon Lake, find out what makes each one so exciting.
Cold Spring
About 50 miles north of Manhattan, Cold Spring compresses riverfront, mountain trails, and a 19th-century Main Street into just a few compact blocks along the Hudson River. Main Street slopes directly toward Dockside Park, where benches face passing sailboats, and the 1893 Cold Spring Depot is steps from the water. Most of the commercial strip falls within the Cold Spring Historic District, its brick and wood storefronts dating largely to the mid-1800s, when the nearby West Point Foundry fueled the village economy.
The foundry’s preserved iron ruins and wooded paths remain inside village limits at the West Point Foundry Preserve, reachable on foot from downtown. Just north along Route 9D, Breakneck Ridge rises sharply from the road, its trailhead minutes from the train line. Antique dealers fill the Cold Spring Antique Center, Cold Spring Coffeehouse pours espresso mid-block, and Pig Hill Inn is a bed and breakfast, a short walk from the river.
Skaneateles
Skaneateles sits at the northern tip of its namesake lake, widely regarded as the cleanest of the Finger Lakes in upstate New York, and supplies unfiltered drinking water to Syracuse. Clift Park’s public pier and swimming area extend the village right onto the lake, while Genesee Street runs inland through the Skaneateles Historic District, lined with 19th-century buildings housing boutique shops, galleries, and cafes like Skaneateles Bakery.
The Sherwood Inn, founded in 1807, remains steps from downtown, offering period rooms just blocks from the waterfront. Narrated cruises on the Judge Ben Wiles steel-hulled boat take guests past wooded slopes and private estates, and the village fills with visitors during the Skaneateles Festival of Music, Antique and Classic Boat Show, and Dickens Christmas.
Cooperstown
Baseball lore collides with Federal-era architecture in Cooperstown at the southern tip of Otsego Lake. Founded in 1786 by American politician William Cooper, much of the quaint village is protected within the Cooperstown Historic District, which includes more than 200 contributing properties on the National Register. And the three-story galleries of the National Baseball Hall of Fame and Museum pull in fans year-round.
A short walk away, the neo-Georgian mansion housing the Fenimore Art Museum looks directly over the lake, while neighboring Fenimore Farm and Country Village (formerly called The Farmers’ Museum) is a museum, country village, and working farm. Lakefront access at Lakefront Park is a great place to enjoy Otsego Lake.
Lake Placid
Travelers tend to talk about Lake Placid's Olympic legacy and Whiteface Mountain. But those looking for something smaller and more intimate will find it equally appealing, as will those who love winter sports. Main Street runs directly along Mirror Lake, with a public path and benches tracing the shoreline. In winter, the lake freezes over and is plowed into a skating loop with marked hockey rinks and a toboggan run built at the south end by the tennis courts.
The same can be said for the Lake Placid Olympic Museum, which is surprisingly intimate with original 1932 and 1980 artifacts, knit Team USA sweaters, and the “Miracle on Ice” gallery inside the Olympic Center on Main Street. Man and Beast, known as “The Adirondack Dog Store,” fills multiple rooms on the south end of Main Street with canine raincoats, hiking boots, and shelves of outdoor gear sized for dachshunds through Great Danes. Up the street, Gallery 46 showcases Adirondack Park artists with one-of-a-kind oil paintings, metalwork, and locally made jewelry.
Woodstock
At the eastern edge of the Catskill Mountains in upstate New York is the town of Woodstock. The 1969 festival happened in Bethel, but the name stuck, and the town still revolves around art, music, and counterculture storefronts along Tinker Street. Within a few compact blocks, Woodstock Artists Association & Museum presents rotating exhibitions by regional artists in a building dating to 1919, while Happy Life Productions has sold hand-dyed tie-dye shirts and bold graphic tees since 1987.
Remedies Herb Shop stocks loose botanicals and incense in glass jars behind a narrow wooden counter, Three Turtle Doves deals in vintage handbags and worn-in leather boots, and the Woodstock Playhouse is a top spot for plays, musicals, and concerts.
Trumansburg
Northwest of Ithaca, along the western shore of Cayuga Lake, is the town of Trumansburg. Its most charming details are found along Main Street, which is lined with tight rows of 19th-century brick buildings topped with Italianate cornices and tall, narrow windows. The small-town scale is apparent in local businesses such as Gimme! Coffee, which pours espresso on East Main Street. The café’s creekside patio backs up to Trumansburg Creek, which runs directly through the village.
The 1851 Greek Revival home of Trumansburg Conservatory of Fine Arts hosts concerts and exhibitions beneath original stained glass. Around the corner, Atlas Bowl has restored 1950s bowling lanes, along with a full kitchen and bar.
Schroon Lake
The Strand Theater lights up Main Street in Schroon Lake with its restored Art Deco marquee and single-screen showings, hosting films, live music, and local performances since 1926. Across the street, Pitkin’s Restaurant and 9 Mile Coffee Co. offer simple, homey meals and coffee with a creekside view. Main Street runs parallel to the west shore of Schroon Lake, with public beach access and a marina.
The Lodge at Schroon Lake offers cabins, chalets, and glamping sites across 36 acres on the lakefront, adding quiet recreational options while keeping the village's intimate and nostalgic scale intact.
Alexandria Bay
Alexandria Bay feels like a fairytale brought to life in upstate New York. James Street runs along the village waterfront, where the Church of Saint Lawrence, built in 1889, sits beside the 19th-century Cornwall Brothers’ Store and small marinas that host kayaks and private boats.
Boldt Castle on Heart Island, constructed beginning in 1900 and left unfinished in 1904 after George C. Boldt’s wife died, is accessible only by ferry or private boat. Its stone walls, turrets, and landscaped grounds feel like something lifted from a storybook, and the surrounding Heart Island gives visitors a contained, enchanting space to explore.
Saranac Lake
Riverside Park opens with two stone teddy bears at the entrance, one father in a fisherman’s vest holding a rod, the other a son with a basket of fresh catch, greeting visitors to Saranac Lake with instant whimsy. The park sits at the crossroads of Main and River Streets, its waterfront framed by Lake Flower and the distant Adirondack peaks.
Downtown streets in this upstate New York town are full of art galleries like the Adirondack Artists Guild, cafés with live music, and shops like the Village Mercantile. For families, William Morris Park is home to a popular attraction, the Adirondack Carousel, a collection of 24 hand-carved regional animals.
Penn Yan
Rivers sparkle at the northeastern tip of Keuka Lake in upstate New York, where Penn Yan balances a working waterfront with a welcoming downtown that takes visitors back to a simpler time. Given the town's strong ties to the Amish and Mennonite communities, it’s not uncommon to see horse-drawn buggies pass by the 19th-century and neoclassical buildings. Main Street stretches through the heart of town with brick storefronts like Longs’ Cards and Books, a multigenerational bookstore, Amity Coffee Co., and the Laurentide Inn B&B, which dates back to 1820.
Families gather at Indian Pines Park, where there is a sandy swim area. Weekends come alive at the Windmill Farm & Craft Market, with Amish quilts, cheese, and produce spilling across 44 tree-lined acres. And the Weaver-View Farms Amish Country Store carries hand-stitched quilts and pantry staples, letting visitors take a piece of Penn Yan home.
Beacon
Beacon sits between the Hudson River and Mount Beacon, close enough to New York City for a spontaneous day trip. The Dia Beacon remains one of the largest contemporary art museums in the country, housed inside a former factory near the waterfront. But the part that makes Beacon feel genuinely adorable can be found along Main Street, a mile lined with intact brick buildings now filled with independent storefronts. Bank Square Coffeehouse spills onto the sidewalk in warmer months, drawing regulars and day-trippers.
Those looking for neat souvenirs may want to check out Play Toys and Gifts, which stocks offbeat games and novelty items. And for those with a sweet tooth, Alps Sweet Shop has been making chocolate on-site since the 1920s. Vintage hunters can head to Blackbird Attic, while Beacon Bath and Bubble mixes bath bombs with retro candy and bottled sodas. Near the waterfall at Fishkill Creek, the Roundhouse boutique hotel and restaurant is housed in a restored 19th-century mill building, with its restaurant overlooking the rushing water.
From Riverside Park’s father-and-son stone bears in Saranac Lake to Windmill Farm & Craft Market’s hand-stitched quilts in Penn Yan, Upstate New York thrives on playful details. Schroon Lake's Art Deco marquee lights up the street near its namesake lake. The legacy of two winter Olympic Games doesn't overshadow the charming dog accessory store in Lake Placid. And the unfinished castle in Alexandria Bay makes visitors feel like they've been placed inside a fairytale. These streets, their carefully maintained history, and their curated personalities prove that they are among the most adorable towns in the state.
