7 Overlooked Towns In Upstate New York Worth Visiting

Upstate New York is home to a wide range of towns shaped by lakes, rivers, mountains, and long local histories. Beyond the region’s major travel corridors, many communities offer experiences rooted in daily life, regional traditions, and close connections to the surrounding landscape. Places such as Hammondsport on Keuka Lake and Aurora on Cayuga Lake reflect this more measured and grounded side of the state. Travelers looking for lakeside downtime, outdoor access, and a sense of local culture will find plenty to explore in these communities. Spending time walking main streets, visiting local institutions, and getting out on nearby water or trails offers a deeper look at the character of peaceful Upstate New York.

Skaneateles

Steeped in history and set along the shore of Skaneateles Lake, Skaneateles provides a classic waterfront setting with a strong sense of continuity. The downtown area is lined with well-preserved 19th-century buildings that house boutiques, galleries, and restaurants, making it easy to spend hours moving between shops and meals. While many travelers focus on Ithaca or Watkins Glen, Skaneateles has its own appeal centered on Skaneateles Lake, one of the cleanest lakes in the country and a primary drinking water source for the City of Syracuse.

There is plenty to do without feeling hurried. An afternoon picnic paired with free summer concerts at Clift Park offers direct access to the water and a relaxed community atmosphere. The Charlie Major Nature Trail follows a former railroad corridor, running alongside a creek for portions of the walk while passing through quieter residential areas. Nearby, Anyela’s Vineyards, located in Skaneateles Falls, offers tastings in a rural setting, while Last Shot Distillery showcases locally made spirits. A dinner cruise with Mid-Lakes Navigation provides time on the water and views of historic lakeside homes.

Saranac Lake

Known for its outdoor focus and active arts scene, Saranac Lake serves as a year-round center of Adirondack life. Once a major health resort town, it retains a practical, lived-in feel, with a downtown that blends historic buildings, local shops, and working galleries. Surrounded by mountains and a network of lakes, it functions as a base for paddling routes, hiking trails, and seasonal recreation. Staying in town allows for a closer connection to its long-standing community.

The area’s medical history is preserved at the Saranac Laboratory Museum, which documents the town’s role in tuberculosis treatment and explains how that period shaped local architecture. Adirondack Lakes & Trails Outfitters, based in town, rents kayaks and organizes guided hikes, though access points vary by season and location. In the evening, the Waterhole Music Lounge draws locals for live performances. During winter, the Ice Palace at the Saranac Lake Winter Carnival remains a major community event, built primarily from ice and snow.

Catskill

Rooted in a long artistic tradition, Catskill has developed into a creative hub with direct access to river and mountain landscapes. It was home to Hudson River School painter Thomas Cole, and that legacy continues through local studios, galleries, and public art. Positioned along the Hudson River and near the Catskill Mountains, the town offers a balance of cultural activity and outdoor space without the density found in nearby river towns.

The Hudson River Skywalk spans the Rip Van Winkle Bridge, offering elevated views of the river and surrounding hills while providing pedestrian access between Catskill and Hudson, though reaching Hudson’s downtown requires additional walking. At the RamsHorn-Livingston Audubon Sanctuary, trails wind through tidal marshlands close to town. Bailiwick Ranch & Animal Park has included exotic animals and remains a stop for families, though operations have varied over time. Food and drink options include Subversive Malting & Brewing and Left Bank Ciders, which focus on small-batch cider made with regional fruit.

Hammondsport

With deep ties to aviation history and a strong winemaking tradition, Hammondsport is a small village with a wide range of attractions. While Finger Lakes visitors often gravitate toward Seneca or Cayuga Lakes, Keuka Lake’s Y-shaped form gives it a different character, and Hammondsport sits at its southern tip. The village square is lined with shops and restaurants, and the pace encourages longer stays rather than quick stops.

Depot Park provides access to the lake for boating, paddling, and lakeside relaxation, though swimming access depends on current local guidelines. OnKeuka! operates boat tours that highlight shoreline views, regional history, and vineyard landscapes. The Glenn H. Curtiss Museum explores the life and work of the aviation pioneer through early aircraft, motorcycles, and regional history exhibits. Nearby wineries include Pleasant Valley Wine Company, recognized as the oldest bonded winery in the Finger Lakes, and Dr. Konstantin Frank Winery, located in the town of Torrey.

Rhinebeck

A mix of history, dining, and seasonal events makes Rhinebeck a consistent draw in the Hudson Valley. Tree-lined streets support independent shops and restaurants, giving the village a strong sense of daily life. While it attracts attention, it is sometimes bypassed by travelers heading farther north or toward larger river towns. Its central location and range of activities make it well-suited for a focused weekend visit.

Wilderstein Historic Site offers insight into 19th-century life along the Hudson through a restored Queen Anne mansion and landscaped grounds overlooking the river. Ferncliff Forest provides trails for hiking and biking, a fishing pond, and a fire tower with wide views of the surrounding valley. During the winter months, Burger Hill becomes a local sledding spot. Rhinebeck also hosts large seasonal gatherings such as the Hudson Valley Sheep & Wool Festival, while other events rotate locations and schedules across the region.

Aurora

Aurora is a village where careful preservation has shaped much of its present-day appearance. Restoration efforts supported by Pleasant Rowland, founder of the American Girl brand, along with later work by the Aurora Foundation, have resulted in a cohesive streetscape anchored by historic buildings and lake views. Its location on the eastern shore of Cayuga Lake keeps it slightly removed from the main Finger Lakes routes.

Bianconi Tours operates seasonal boat trips on Cayuga Lake, with offerings that vary by time of year. A major draw is the MacKenzie-Childs headquarters, where visitors can tour the restored farmhouse, observe artisans, and walk the surrounding grounds. Dining at 1833 Kitchen & Bar pairs local ingredients with views of the lake inside a historic inn. The Spa at the Inns of Aurora offers wellness services set directly along the shoreline.

New Paltz

As a college town with a long counterculture history, New Paltz blends academic life, outdoor access, and a busy main street. Main Street includes record stores, international restaurants, and long-standing local businesses shaped by the student population. The result is an atmosphere that rewards spending time in town rather than passing through.

Biking options include rentals from New Paltz Biking, with access to sections of the River-to-Ridge Trail that link town to surrounding farmland and foothills. Some trail segments are still evolving, but the route already provides a strong connection between town and landscape. The Nyquist-Harcourt Wildlife Sanctuary offers quieter walking paths near the village center. The Mohonk Preserve Testimonial Gateway marks the entrance to a large preserve with miles of carriage roads for hiking and biking. Twin Star Orchards, a short drive away, serves wood-fired pizza and house-made cider.

Stay Curious

These towns reflect an Upstate New York shaped by work, weather, and long memory. Vineyards, museums, trail networks, and waterfronts exist as part of daily life, not as set pieces. Time here tends to slow naturally, allowing space for conversation, routine, and return visits. Rather than destinations to check off, these places offer continuity, rewarding travelers who stay curious and pay attention.