Top Towns to Visit in Upstate New York

Upstate New York is loosely defined as anything north of New York and Long Island. Sometimes certain additional counties are excluded, but sometimes not. There is no precise definition of what “upstate” means, but the general notion is anything outside of dense metropolises. While that excludes much of the population, it does include the vast majority of New York State’s landmass – and what a beautiful state it turns out to be. There are several key regions to focus on, including the Hudson River, the Finger Lakes, several mountain ranges, and the list goes on. As you travel through this beautiful region, keep an eye out for the following small towns worth visiting.

Lake Placid

The Lake Placid ski lift in the fall.

Lake Placid puts the ‘At the top’ in upstate New York. This village in Essex County is the northernmost community on this list. What better way to clear the mind and rejuvenate the spirit than in the crisp air of the Adirondack Mountains. You will indeed feel the resounding glory of the site which has twice hosted the Winter Olympics. Lake Placid is full of inspiring views, outdoor recreation, and a friendly mountain town vibe to top it all off.

Skaneateles

Shops and <a class=restaurants at Skaneateles Lake in Skaneateles, New York” data-src=”https://www.worldatlas.com/r/w768/upload/48/74/4f/shutterstock-1998814253.jpg”/>
Shops and restaurants at Skaneateles Lake in Skaneateles, New York. Editorial credit: PQK / Shutterstock.com

This Onondaga County hamlet sits atop Skaneateles Lake, which is one of the eleven Finger Lakes. The upscale city offers a relaxing waterfront atmosphere where one can unwind for a few days at the city’s famous inns and small B&Bs. Skaneateles is also a great place to appreciate history. Many homes in town are hundreds of years old and were part of the Underground Railroad.

Ithaca

Ithaca Falls in Ithaca, New York
View of Ithaca Falls on the campus of Cornell University in the Falls River Gorge, Ithaca, New York.

Ithaca, located in Tompkins County, sits at the southern tip of Cayuga Lake, another of the Finger Lakes. The iconic buildings of the Ivy League City Champions can be found all over the Cornell University campus. The charm continues in downtown Ithaca Commons and the lush natural surroundings, including gorges, waterfalls, and inspiring viewing trails. Ithaca’s population nearly doubles during the school year, which invites a more vibrant energy compared to some of the quieter communities in the area.

Lake George

Steamboat carrying tourists to view the Lake George waterfront in Lake George, New York
Passenger steamer carrying tourists on a cruise to see the sights of the Lake George waterfront and the surrounding Adirondack Mountains in Lake George, New York. Editorial credit: splask / Shutterstock.com

The small town of Lake George, located in Warren County, is another soothing pairing of the Adirondack Mountains and a bright blue lake (also called Lake George). But like Lake Placid, Lake George has its own unique impulse to complement the landscape. Tourists should be sure to navigate the vintage downtown area, and if they want to go camping, there are plenty of small islands to pitch a tent on. You can even have the place to yourself for the night. Lake George also has a strong year-round arts scene to immerse yourself in.

Canandaigua

The Ontario County Courthouse stands out on Rochester in downtown Canandaigua, New York
The Ontario County Courthouse stands out in Rochester in downtown Canandaigua, New York.

Canandaigua is a town in Ontario County, at the northern tip of Lake Canandaigua, the third Finger Lake to be mentioned so far. The 12.55 km² town is surrounded by the 161.95 km² town (both similarly populated). The city is rightly called “The Chosen Place” which translates from the modern tuscaroran title. Canandaigua offers another elegant Laketown experience, from the pristine shoreline to its elegant Main Street, to the manicured and captivating Sonnenberg Gardens.

sleepy hollow

Old Dutch Church in Sleepy Hollow, New York
Old Dutch Church in Sleepy Hollow, New York. Editorial Credit: LEE SNIDER PHOTO IMAGES / Shutterstock.com

The city is located on the eastern banks of the Hudson River, just 30 miles from New York. This picturesque and colorful village is part of the ironically and oddly named town of Mount Pleasant in Westchester County. Some people exclude this area from their “New York” borderline, but Sleepy Hollow is like an entirely different world than New York, and so it’s well within the scope of this list. Enjoy the beautiful scenery while keeping an eye out for the Headless Horseman (or at least the iconic statue).

cold spring

People walk along the main shopping district in Cold Spring, New York
People walk along the main shopping district in Cold Spring, New York. Editorial credit: James Kirkikis / Shutterstock.com

Just up the Hudson River from Sleepy Hollow is the village of Cold Spring, which resides in Philipstown in Putnam County. The half-mile-long Main Street is full of old-fashioned general store/bookstore/apothecary/restaurant type businesses. The pretty community is engulfed by beautiful green mountains ready to be explored on foot. Head to the ruins of the Cornish Estate, or for a more strenuous hike try the popular Breakneck Ridge for excellent views across the river valley. And if you have the chance, drive up the road (and, even better, over the water) to check out Bannerman’s Castle on Pollepel Island.

Glen Watkins

Seneca Lake, Watkins Glen, New York
Seneca Lake, Watkins Glen, New York.

This Schuyler County village, located at the southern end of Seneca Lake (the fourth and final Finger Lake to make this list), is home to barely 2,000 people and yet is a major tourist draw. Like many communities in the Finger Lakes region, Watkins Glen is full of natural beauty. The charming pier welcomes boaters and swimmers at the base of long, straight, and beautiful Seneca Lake. Watkins Glen State Park reveals another side of the landscape – with 19 waterfalls (which you can get up close to), hundreds of campsites, and plenty of memorable hiking trails. This humble village is also full of surprising activities with the Watkins Glen International, a major motor racing circuit that tells the story of motor racing around the town.

Woodstock

Streets and shops in Woodstock, New York
Streets and stores in Woodstock, New York. Editorial credit: solepsizm / Shutterstock.com

Although the famous festival was held near Bethel, the name and theme lives on in today’s Woodstock. This Ulster county hippie/hipster town features live music, vegan culture and around 20 colorful mum and pop shops all along Tinker Street. Woodstock has been known as a place of free and creative expression since the first artists’ colony was established in 1903. Since then, renowned musicians like Dylan and Bowie, as well as authors such as Neil Gaiman and Amy Tan, have set up shop in Woodstock. It’s a beautiful place to do beautiful things.

New Paltz

Mohonk Mountain House in New Paltz, New York
Mohonk Mountain House on a lake with a dock and a small rocky island in New Paltz, New York.

New Paltz is another Ulster county town known for its eye-catching aesthetic. This charming community sits beside the modest Wallkill River and touches on different aspects of visual appeal. For starters, the boutique cafes and boutiques of Main Street are definitely worth a visit. Next, the 17th century architecture of Rue Historic Huguenot begs to be admired. From here, one can visit the Mohonk Preserve, which uses a network of motorable roads and trails to explore the Shawangunk Mountains. Finally, a short distance away is the picturesque Mohonk Mountain House, which rises dramatically above Lake Mohonk, with a backdrop of endless evergreen forest.

Saugerties

The Saugerties Lighthouse in Saugerties, New York
The Saugerties Lighthouse in Saugerties, New York. Editorial credit: James Kirkikis / Shutterstock.com

To complete Ulster County’s trifecta of beauty, be sure to skip Saugerties, the town and village within the town, still of the same name. Saugerties is serenely positioned between the Hudson River (to the east) and the Catskill Mountains (to the west). The natural surroundings perfectly complement the pretty downtown, with a matinee theater, cafes, and cool restaurants you’d hope to find in a small upstate town. The postcard-worthy image comes from the Saugerties Lighthouse – a faded red brick house built in 1869 on the banks of the Hudson River.

Hyde Park

Hyde Park, New York
Hyde Park, New York.

The small town of Hyde Park, located in Dutchess County, has a distinct historical and architectural beauty. For starters, there’s the house of Franklin D Roosevelt, which is a National Historic Site. The Springwood Estate was not only the home of the 32nd President of the United States, who served a record four terms, but also the home of Eleanor Roosevelt and the Presidential Library and Museum of FDR, who was the first in the gender. Next on the list is the late 19th-century Beaux-Arts-style Vanderbilt Mansion, another National Historic Landmark that teaches about the Vanderbilt family’s contributions to the development of New York State. Finally, the quaint hamlet of Staatsburg dates back to 1693, when Captain Henry Pawling purchased a small piece of land from Native Americans.

Rhinebeck

Crowds of visitors to the Dutchess County Fair in Rhinebeck, New York
Crowds of visitors to the Dutchess County Fair in Rhinebeck, New York. Editorial credit: Alexanderstock23 / Shutterstock.com

Further up the east bank of the Hudson River in Dutchess County is the town and village of Rhinebeck. This place has one of those quintessential downtowns, where trees dot the sidewalks, making them feel tighter but in a relaxed way. This brings pedestrians closer to artisan shops and restaurants, among which there are many high-caliber options. The village catches the eye with its enchanted castle architecture which makes up its various historical sites, its hotels/inns and even its converted restaurants.

Upstate New York is where beauty and boundaries are hard to grasp. I hope this list does the area justice and only inspires you to explore even further.

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