The village center of Skaneateles, New York on a quiet autumn morning via DebraMillet / iStock.com

6 Most Memorable Small Towns in Upstate New York

Upstate New York is a memorable destination in itself, known for its abundance of lakes, such as Lake Ontario and Lake Champlain, and majestic mountains, including the Adirondack Mountains and part of the Appalachian Mountains. Regardless of the time of year, adventure awaits in the form of festivals and events, unique outdoor destinations, and storied histories readily available in museums. The area explodes with vibrant communities and breathtaking destinations, all of which visitors may experience in some of the most memorable small towns of Upstate New York.

Skaneateles

Street view at Skaneateles, New York
Street view at Skaneateles, New York

Skaneateles is one of the most picturesque towns in New York, home to the Skaneateles Lake and situated in the Finger Lakes region. Skaneateles Lake is one of the cleanest lakes in the country, ideal for boating, swimming, and enjoying summer days. In autumn, wine tasting and apple picking are popular activities, while winter is the ideal time to experience the annual Dickens Christmas celebration. Travelers may enjoy aerial views of the town with a hot air balloon ride, or hop aboard Mid-Lakes Navigation for a sunset cruise along the sparkling water. Plus, the Skaneateles Antique and Classic Boat Show draws in a crowd from all over the country.

Alexandria Bay

The view of waterfront homes in Alexandria Bay surrounded by striking fall foliage along St Lawrence River
The view of waterfront homes in Alexandria Bay surrounded by striking fall foliage along St Lawrence River, via Khairil Azhar Junos / Shutterstock.com

Alexandria Bay is one of the most adorable small towns in Upstate New York. Helicopter and hot air balloon rides are a great way to view the town and the surrounding 1000 islands, while boat tours offer a close-up view. Guided fishing charters are a great option for anglers, while families will enjoy mini-golf, batting cages, go-karts, arcade games, and more. There is also an endless array of annual events and festivals such as Bill Johnston’s Pirate Days, the Annual Powerboat Poker Run, and the Blues in the Bay Festival. A turn-of-the-century castle, Boldt Castle, sits just across the bay on Heart Island easily accessible by boat and opens in spring.

Hudson

Warren Street in downtown Hudson, New York.
Warren Street in downtown Hudson, New York. Image credit quiggyt4 via Shutterstock.com

Hudson sits on the shores of the Hudson River and boasts easy access to the Hudson Valley and the Catskill Mountains. Promenade Hill is a wonderful destination to watch the sun go down, painting the river in golden light, while the Catskill Mountains offer plenty of camping and hiking opportunities. History lovers delight at historic buildings such as Olana, which dates back to 1872. The town's Warren Street is the best destination for an afternoon stroll and shopping trip, home to local boutiques such as 314 Warren, Clove & Creek Hudson, and Hidden Gem.

Cranberry Lake

Sunset over Cranberry Lake in the Adirondack Mountains.
Sunset over Cranberry Lake in the Adirondack Mountains.

Cranberry Lake is a picture-perfect town in the Adirondack Mountains, surrounded by forests and the sparkling Cranberry Lake, which is the third-largest lake in the Adirondacks. Because of its proximity to the water, boating, kayaking, canoeing, paddling, swimming, rafting, fishing, and more, are all popular activities in the area, making for an especially memorable trip. There is also a plethora of trails in the Cranberry Lake Wild Forest, making it the ideal destination for outdoor adventurists. The Cranberry Lake Campground is one of the more remote areas in the state, offering views of the sparkling night sky away from city lights, as well as a chance to decompress and unwind in nature.

Paul Smiths

Paul Smiths College campus at Paul Smiths, New York.
Paul Smiths College campus at Paul Smiths, New York.

Paul Smiths is one of the most scenic Adirondack Mountain towns, located on the glassy waters of Lower Saint Regis Lake and 12 miles northwest of Saranac Lake. Kayaking, fishing for northern pike, and bird watching are all great activities to enjoy. Of course, visitors also hike along the Adirondacks, which feature breathtaking views at one of the many lookout points. In winter, skiing, snowshoeing, and snowmobiling are popular activities. Plus, the nearby Saranac Lake Winter Carnival offers the opportunity to delve into the excitement and joy of the season, whether it is a family vacation or a romantic getaway.

Wilmington

Whiteface Mountain , Wilmington, New York.
Whiteface Mountain , Wilmington, New York. Editorial credit: nyker / Shutterstock.com

Wilmington is another destination in the foothills of the Adirondack Mountains, situated northeast of Lake Placid. It is one of the most beautiful towns in the Adirondack Mountains, home to Whiteface Mountain, where visitors hike to the summit or drive up the Whiteface Veterans Memorial Highway and revel in views of the surrounding natural area. The Flume is another especially popular area, with a series of waterfalls and swimming holes along the Flume Trail System. High Gorge Falls is especially beautiful, featuring a 700-foot waterfall and picturesque high cliffs. Anglers enjoy fly fishing in the West Branch of the Ausable River, as well as mountain biking in the summer months, or skiing down the Whiteface Mountain.

Enjoy an Unforgettable Trip to Upstate New York!

The small towns of Upstate New York offer unforgettable adventures, from the breathtaking stone path along Whiteface Mountain, boasting views of Lake Placid and the Adirondack Mountains, to the beautiful Boldt Castle of Alexandria Bay. While the awe-inducing sights of the area are some of the most memorable, the small-town charm, unique histories, and welcoming communities all add to the allure of each destination, promising unmatched memories and special experiences.

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