The Most Beautiful Towns To Visit In Upstate New York

Upstate New York is loosely defined as anything north of New York City 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 the dense metropolitans. Though this excludes a large portion of the population, it includes 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 hone in on, including the Hudson River, the Finger Lakes, multiple mountain ranges, and the list goes on. As you travel to this beautiful region, keep an eye out for the following small towns that are well worth visiting. 

Lake Placid

The Lake Placid Ski Lift in autumn.
The Lake Placid Ski Lift in autumn. 

Lake Placid puts the 'Up' in Upstate New York. This Essex County village is the Northernmost community on this list. What better way to clear the mind and rejuvenate the spirit than in the fresh air of the Adirondack Mountains. One will indeed feel the reverberating glory from the two-time host site of the Winter Olympic Games. Lake Placid is filled with inspiring views, outdoor recreation, and a friendly mountain-town feel to cap it all off. 

Skaneateles

Shops and restaurants in Skaneateles Lake in Skaneateles, New York
Shops and restaurants in Skaneateles Lake in Skaneateles, New York. Editorial credit: PQK / Shutterstock.com

This Onondaga County hamlet sits at the top of Skaneateles Lake, which is one of eleven of the Finger Lakes. The upscale town offers a relaxing waterfront atmosphere where one can unwind for a couple of days in the town's famous inns and small B&Bs.  Skaneateles is also a great spot to appreciate history. Many of the homes throughout 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, rests at the southern tip of Cayuga Lake, another of the Finger Lakes. The classic Ivy League town champion iconic buildings are all throughout Cornell University's campus. The charm continues into the downtown Ithaca Commons and out into the lush natural surroundings, including gorges, waterfalls, and inspiring lookout trails. The population of Ithaca nearly doubles during the school year, which invites more vibrant energy compared to some of the quieter communities throughout the region. 

Lake George

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

The small town of Lake George, situated in Warren County, is another soul-soothing pairing of the Adirondack Mountains and a crisp blue lake (also called Lake George). But like Lake Placid, Lake George has a unique pulse of its own to complement the scenery. Tourists must make sure to cruise the vintage downtown core, and if they wish to enjoy camping, there are numerous small islands to pitch a tent on. One may even have the place to yourself for the night. Lake George also has a solid, year-round arts scene to delve into. 

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 and city, in Ontario County, at the northern tip of Canandaigua Lake, the third Finger Lake to receive mention so far. The 12.55 sq. km city is surrounded by the 161.95 sq. km town (both similarly populated). The city is aptly referred to as "The Chosen Spot," which translates from the modern Tuscaroran title. Canandaigua offers another elegant laketown experience, from the pristine shoreline to its classy Main Street, to the well-kept and captivating Sonnenberg Gardens

Sleepy Hollow

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

The town is situated on the eastern banks of the Hudson River, only about 48km from New York City. This quaint and colorful village is part of the ironically and eerily-named town of Mount Pleasant in Westchester County. Some people exclude this region from their "Upstate New York'' boundary, but Sleepy Hollow is like an entirely different world compared to New York City, and so it is well within the scope of this list. Enjoy the lovely scenery while keeping one eye open for the Headless Horseman (or at least the iconic statue). 

Cold Spring

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

Just up the Hudson River from Sleepy Hollow lies the village of Cold Spring, which resides within Philipstown in Putnam County. The half-mile-long Main Street is packed with old-fashioned businesses of the general store/bookshop/apothecary/restaurant variety. The cute community is engulfed by beautiful and verdant mountains that are ready to be explored on foot. Make for the Cornish Estate Ruins, or for a more intensive hike, try the popular grind-up Breakneck Ridge for excellent views of the river valley. And if you get a chance, head up the road (and, even better, out on the water) to check out Bannerman Castle on Pollepel Island. 

Watkins Glen 

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

This Schuyler County village, situated on the southern end of Seneca Lake (the fourth and final Finger Lake to make this list), is home to barely 2,000 residents and yet is a major tourist draw. As with many communities in the Finger Lakes region, Watkins Glen is rife with natural beauty. The charming pier welcomes boaters and swimmers alike to the base of the long, straight, and splendid Seneca Lake. Watkins Glen State Park reveals another side of the scenery - complete with 19 waterfalls (some of which you can get up close and personal with), hundreds of campsites, and many memorable hiking trails. This humble village also packs some surprising action with the Watkins Glen International, an important racetrack that roars of the auto-racing history around town. 

Woodstock

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

Even though the famous festival took place near Bethel, the name and theme live on in modern-day Woodstock. This hippie/hipster Ulster County town, showcases live music, vegan culture, and a score of colorful mom n' pop shops all along Tinker Street. Woodstock has been known as a place for free and creative expression ever since the first artist colony was formed in 1903. Since then, big-name musicians like Dylan and Bowie, as well as authors such as Neil Gaiman and Amy Tan, have set up shop in Woodstock. It is a beautiful place to do beautiful things.

New Paltz

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

 New Paltz is another Ulster County town known for its eye-catching aesthetic. This charming community sits next to the modest Wallkill River and touches on different aspects of visual appeal throughout. For starters, the boutique cafes and shops along Main Street are definitely worth a gander. Then, the 17th-century architecture of the Historic Huguenot Street is just begging to be admired. From there, one can visit the Mohonk Preserve, which utilizes a network of carriage roads and trails to explore the Shawangunk Mountains. Finally, only a short distance away is the picturesque Mohonk Mountain House, which sits dramatically above Lake Mohonk, with a backdrop of infinite 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 the Ulster County trifecta of beauty, make sure to hop over to Saugerties, the town and the village within the town, still of the same name. Saugerties is serenely positioned between the Hudson River (to the east) and Catskill Mountains (to the west). The natural surroundings perfectly complement the pretty downtown core, complete with a matinee theater, coffee shops, and cool restaurants that you would hope to find in a small, upstate town. The postcard-worthy picture comes from the Saugerties Lighthouse - a faded red-brick house built in 1869 on the shores of the Hudson River. 

Hyde Park 

Hyde Park, New York
Hyde Park, New York. 

The small town of Hyde Park, situated in Dutchess County, has a distinct historical and architectural beauty. For starters, there is the Home of Franklin D Roosevelt, which is a National Historic Site. The Springwood Estate was not only home to the 32nd President of the United States, who served a record four terms, but also the home of Eleanor Roosevelt and the FDR Presidential Library and Museum, which was the first of its kind. Next on the list is the late 19th-century Beaux-Arts-style Vanderbilt Mansion, another National Historic Site 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 plot of land from the Native Americans. 

Rhinebeck

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

Further up the eastern shores of the Hudson River in Dutchess County, lies the town and village of Rhinebeck. This place has one of those quintessential downtown cores, where the trees dot the sidewalks, making them tighter but in a relaxed way. This brings pedestrians closer to the artisanal shops and eateries, from which there are many high-caliber options to choose from. The village draws the eye with its enchanted-castle-esque architecture that makes up its various historical sites, hotels/inns, and even converted restaurants. 

Upstate New York is where beauty and boundaries are difficult to comprehend. I hope this list does the region justice and that it only makes you want to explore even further.

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