8 Cutest Small Towns In Upstate New York For 2025
Get out of the big city and explore some of New York's more modest offerings this year. When you move upstate, you almost immediately leave a landscape of concrete jungles and shift into one of the most lush and pristine regions of the country. From the verdant Hudson Valley to the Adirondack Mountains, there are numerous small towns you ought to visit while adventuring around.
Today, we will be recommending the cutest of these communities that could accommodate you, each known for its charm, peaceful atmosphere, and variety of attractions.
Windham
Windham functions as an idyllic travel destination year-round, but its busiest stretch is November through March, when Windham Mountain opens its 54 trails to skiers and snowboarders. The resort has steadily expanded since the 1960s and now includes a snow tubing park, Nordic center, and a small base village with equipment rentals and slope-side dining, making it one of the top ski destinations in New York hands down.
Outside the winter season, the mountain transitions into a hub for hiking and mountain biking, with the lifts still operating for cyclists and scenic views of the northern Catskills.
A public walking path along the Batavia Kill (a meandering creek flowing nearby) makes way for a lighter stroll in town, while the Windham Path trail network and CD Lane Park offer picnic areas and access to local wetlands in warmer months. One stop if you're walking from one trail area to the other should definitely be the Windham Fine Arts gallery, located in a restored carriage house downtown. The gallery displays rotating exhibits with a regional focus.
Then, in early autumn, the annual Windham Autumn Affair draws yet more crowds for craft vendors and local food stands. Or, escape the noise and hike the woods, getting an up-close glimpse of the trees as they change color. In fact, this quiet community that sits in the foothills around the Catskills is among the best for leaf peeping in New York, attracting landscape photographers from all around.
Watkins Glen
Watkins Glen is best known for its state park, where Glen Creek cuts through a deep gorge and passes numerous stone bridges and alongside 19 different waterfalls. The main trail, open seasonally, follows the gorge floor for about two miles and includes narrow staircases, erosion-carved tunnels, and consistent views of layered shale walls. It is widely considered one of the most beautiful walks in the state, and a must-visit location if you're in the area. The park’s entrance also conveniently sits directly in town, making it easy for you to even walk right from your hotel to the trailhead without needing a car.
The village is also notable for being located at the southern tip of Seneca Lake, and the waterfront area in town includes a public marina, seasonal lake cruises, and a walkable pier that extends into the water. Moreover, the surrounding hills support a cluster of wineries that form part of the Seneca Lake Wine Trail, many within a 10-minute drive.
Watkins Glen International, located just outside the village, may take the attention away from the area's natural landmarks, and often draws national attention with NASCAR events and vintage car races. So, why not spend your apres-hike watching an exhilarating race this summer?
Cold Spring
Cold Spring sits on the east bank of the Hudson River, about 50 miles north of Manhattan, making it a huge draw for day-trippers and weekend traffic. Its direct Metro-North rail access doesn't hurt its reputation as a cute small town getaway either.
For outdoor adventurers, the Hudson Highlands State Park Preserve borders the town, with trailheads to Breakneck Ridge just minutes from the train station. Moreover, scenic views of Storm King Mountain and the river’s widest bends help explain the town’s popularity among painters of the Hudson River School. Even before the widespread use of cameras, Cold Spring has very understandably been a hotspot for artists with an eye for nature.
In town, historic locales like the Cold Spring Depot, a former 1893 railway station turned tavern, provide outdoor dining with views of the river and passing trains. Another must-see is the West Point Foundry Preserve. Once a major arms manufacturer, it now serves as an open-air museum with ruins, trails, and interpretive signage spread throughout its grounds.
Continue your stroll and head next door to the Boscobel House and Gardens, the site of a mansion dating back to 1808, surrounded by well-maintained orchards, gardens, a vast lawn, and other scenic green spaces.
Andes
Andes is a small, one-road town nestled in the Catskills. It can definitely be described as cute, with most being attracted to it for its peacefulness and, better yet, a near-complete lack of crowds. With little in the way of modern development, locales like The Andes Hotel or the Andes Society of History and Culture, with their old-school timber frames, stand out.
Close to the downtown strip lies the Rail Trail, which stretches for just under two miles along the old D&H railroad bed, passing through wetlands, farm fields, and shaded woodland. It's a great way to really get out and see the land for yourself, whether you're biking, running, or walking. Andes is one of the closest towns to the sizable Pepacton Reservoir, where you can fish or paddle too (with a DEP permit).
The surrounding area is also very rural, homing farms that support local businesses like Wayside Cider, which operates a taproom and kitchen just outside the village center.
Ellicottville
Ellicottville is yet another highly active four-season destination in New York. Its two main ski resorts, Holiday Valley and HoliMont, operate independently but together support dozens of trails, terrain parks, and off-season hiking and biking routes. Holiday Valley also runs a high ropes course and a public golf course, while HoliMont, though private, opens facilities to non-members during weekdays.
Many buildings located in town are well over 100 years old, with intact brick façades now housing restaurants, a brewery, gear stores, a selection of hotels, and other useful amenities for your stay. Learn more about the community at the Ellicottville Historical Society Museum, which covers the area’s development from farmland to ski hub, then grab a drink at your choice of either the Winery of Ellicottville or the Ellicottville Brewing Company, the latter being one of the most highly rated brewpubs in the entire state.
One more worthwhile attraction close by is Griffis Sculpture Park. Located a less than 15-minute drive north, this unique park boasts hundreds of sculptures strewn around various fields, ponds, and woodlands. The installations range from classical styles to more interactive pieces that anyone can enjoy.
Alexandria Bay
Resting on the edge of the St. Lawrence River, in the heart of the Thousand Islands region, Alexandria Bay serves as quite the underrated destination for anyone looking to spend some time by the water. Most everything here revolves around its waterways, with tour boats, marinas, and private docks dominating the shoreline.
Boldt Castle, located on Heart Island just offshore, is perhaps the area's official landmark. Built in 1900 by hotel magnate George C. Boldt and left unfinished for decades, the castle is now fully restored and open to visitors via ferry or private boat. Nearby, the stone-built Power House and the yacht house on Wellesley Island also allow public access.
In the village itself, the commercial strip runs along James Street with waterfront amenities everywhere, including canoe, kayak, and boat rentals at various shops. For a guided experience, Uncle Sam Boat Tours operates daily excursions through the islands, including trips across the international border to Canadian waters. Furthermore, the Thousand Islands Historical Museum provides background on local shipping, fishing, and even the region's smuggling routes during the prohibition era.
Note that Alexandria Bay is relatively seasonal, with most businesses open from late spring through early fall, but its concentration of historic and maritime sites, along with many great views, makes it a key stop during these warmer months of the year.
Skaneateles
If you're visiting the Finger Lakes region, Skaneatles is among the most iconic destinations. Its cozy downtown core and proximity to several excellent natural landmarks, like parks and other lakefront spaces, make it an all-around great spot for a weekend escape.
Skaneatles' downtown core runs along Genesee Street, where preserved 19th-century buildings now house small businesses, bars, and restaurants. The town is known for its strict zoning laws, which have preserved both its architectural charm and its unspoiled lakefront. For this reason, the Sherwood Inn, operating since 1807, remains a popular spot for lunch and overnight stays. Many also come in the summer during the Skaneateles Festival, which brings world-class musicians to play shows all around town in various indoor and outdoor venues.
The lake itself, one of the cleanest in the state, is the central attraction for most. Here, you can take public boat tours on the historic Judge Ben Wiles or rent kayaks for self-guided exploration. On land, Clift Park houses a public pier and swimming area just steps from downtown. Be sure to take a trip on the roadways around the lake, too, where scenic drives lead to farm stands, world-class wineries, and quiet lookouts.
If you happen to be a golfer, book a round at the Skaneateles Country Club, which borders Skaneatles Lake and features amazing views regardless of where you are on the course.
Ticonderoga
This location is a good one for history buffs, as Fort Ticonderoga dominates the narrative here. Built by the French in 1755 and contested through multiple wars, the site now remains active in other ways. It is not just a preserved fort, but has a working historical campus with live artillery demonstrations, exhibits, and ongoing archaeological work. You can get a unique view over the fort too, and high above the surrounding area in general, at Mount Defiance, located just south of town. The mountain's top is accessible by car or on foot.
Experience more of the area's natural sights along the La Chute River. Once lined with paper mills, it connects Lake George to Lake Champlain, running through the center of town. A short riverwalk leads not only past several small parks and woodlands, but also to the Ticonderoga Heritage Museum as well.
For a more out-of-this-world museum experience, downtown Ticonderoga is home to the Star Trek Original Series Set Tour. As you could imagine, this indoor attraction has faithfully reconstructed the set from the original 1969 sci-fi series.
Experience Upstate New York Through These Charming Towns
The summer of 2025 is fast approaching, and what better way to spend your weekend than hiking in the woods, swimming in lakes, and experiencing the charms of nearby small towns? Do just that at any of the communities mentioned above, from Watkin Glen's iconic parkland to Alexandria Bay's riverside delights, and Ticonderoga's long-standing history and more. How many of these cozy spots will you check out this year in the Empire State?
