Shops and Restaurants on Skaneateles Lake in upstate New York, view from the pier.

The 10 Best Small Towns In New York To Chill Out

We all know New York State for cities like “The Big Apple” and Buffalo, but it offers much more than busy metropolitan centers and skyscrapers. The best small towns in New York escape the noise, embrace nature, and emphasize each land’sland’s distinctive features without trying to fit in with modernizations and evolutions. Read along as we delve into a list of the best small towns in New York located roughly a few hours away form major cities in the state. 

Mount Tremper

Zen Mountain Monastery in Mount Tremper, Catskills, New York
Zen Mountain Monastery in Mount Tremper, Catskills, New York

Mount Temper, or what is known as Tremper Mountain, is one of the many mountain towns and Hamlets located in Ulster County in the state of New York. It is a town for those who embrace nature and love to be isolated from the fast and busy life in the city. Home to vast farmlands and outdoor sports and activities, Mount Tremper is famous for its Old Jeep trail, The Temper Mountain Fire Tower, and skiing season fun in its snowy winters. Additionally, you can go lodging and enjoy local arts and entertainment nearby, such as the Phonieca festival and the Shandanken theatrical society. 

High Falls

Buildings in the High Falls Historic District
Buildings in the High Falls Historic District

A place of its unique vibe, High Falls is a hamlet located in Hudson Valley. It is a destination for those seeking a sense of small community, unique local culture, or interest in the town’s history. The Roundout Creek waterfall is from where the place gets its name, known to be a wholesome and cute small town. The town is rich with small local businesses and is home to main natural trails and hiking paths such as the Labyrinth Trail and Bonticou Trail. 

Skaneateles

Shops, Restaurants and Condominium on Skaneateles Lake, view from the pier
Shops, Restaurants and Condominium on Skaneateles Lake, view from the pier

Skaneateles is a unique lakeside destination, a small, vibrant town known for its super clear waters and lake-surrounding shops, restaurants, and tourist attractions such as art galleries and museums. Skaneateles is considered a high-end community for its wealthy residents of celebrities and beautiful enchanting nature. Aside from visiting the famous lake Skaneateles, visitors also tend to visit the town for its calming, beautiful parks, art galleries, and historical society, such as the Skaneateles Creamery, which was transformed into a museum to showcase the history of the small town. 

Cold Spring

Boutiques and independent stores populate the charming historic downtown Cold Spring, New York.
Boutiques and independent stores populate the charming historic downtown Cold Spring, New York, via James Kirkikis / Shutterstock.com

A village in the town of Philipstown in Putnam County, NY, owes its name to the time George Washington visited its natural spring, took a sip, and thought it was somewhat chillier than he expected. Main street businesses include antique shops, coffee houses, and restaurants with beautiful surrounding outdoor dining. Some popular attractions include Anthony’sAnthony’s Nose hiking trail and Old Cornish Trail, a true nature-centric town for peace of mind and spiritual awakening experiences. 

Ithaca

Students at Libe Slope watching sunset on campus of Cornell University
Students at Libe Slope watching sunset on campus of Cornell University, via Jay Yuan / Shutterstock.com

Land of waterfalls and wholesome vibes, Ithaca is nestled in New York’sYork’s Finger Lakes region and is known to be a college and university town with enchanting nature views. Visit the Johnson Museum of Art, the Museum of the Earth, Newfield covered bridge, and the beautiful Cascadill Gorge. There is so much to do and see in this lovely small town, and it all contradicts the standard big busy city vibe that everyone associates with New York and the big apple. 

Saratoga Springs

Early afternoon autumn aerial photo view of Saratoga Springs New York
Early afternoon autumn aerial photo view of Saratoga Springs New York

A small city in Saratoga County, NY, Saratoga Springs is known for its infamous horse race tracks and healing mineral waters. The town was once known to be a wealthy family’s destination for nature adventures, horse race betting, and hiking trips. Today Saratoga Springs is any nature lover or art enthusiast’s destination for a trip to escape the usual. The purity of the city and the incredible surrounding nature adds a sophisticated vibe to the place and makes it a classy weekend vacation spot. Some of the many waterfalls in the area include Spier Falls, Cohoes Falls Park, and Snook Kill Falls, located 4 miles north of the city. 

Woodstock

legendary Woodstock village, streets and store, architecture details
Legendary Woodstock village, streets and store, with unique architecture details

Once a wholesome hippie destination, Woodstock is known for the great Rock n Roll festival that turned into a trainwreck in July 1999. The history of the place is highly associated with concerts among people who never visited before, but for locals, Woodstock is still a peaceful green farm town rich with agricultural productions and local farmer markets. Additionally, you can enjoy spa resorts, shop at cute local businesses, and visit the Bluestone Wild Forest. 

Woodstock wouldn’t be as known globally if it wasn’t for the popular Trainwreck concert. It would otherwise remain a peaceful hidden gem that not many know about, like many other cities and towns on this list. Small local shops include potteries, music memorabilia, and vintage thrift shops that tourists enjoy and recommend when visiting. 

Beacon

Landscape view of the corner of Main Street and South Street in Beacon
Landscape view of the corner of Main Street and South Street in Beacon

Beacon is home to contemporary art museums located in Dutchess County, NY. One of its main attractions includes Dia Beacon, a massive modern art museum that brings in thousands of monthly visitors. It was named to commemorate the historic fires that once blazed from Fishkill Mountains to alert the British armies. Clutter is another artistic community gallery in Beacon Ny worth a visit if you’re ever in town, along with Hudson Beach Glass, located on the main street of Beacon, NY. Enjoy a walk to the local farmer's market or along the long dock park through streets rich in vibrant Victorian houses and a green landscape.

Amenia

Aerial view of Amenia, New York
Aerial view of Amenia, New York

Amenia offers the perfect balance of country and busy city vibes, it is surrounded by larger cities and known for maintaining its authenticity by being home to mostly conservative American families. Embracing of its simplistic and religious history, the town is located in Dutchess County between the state border with Connecticut. Peaceful and historic, Amenia was established in 1788 and is home to cultural architecture. The most popular historic attraction includes “The House of Worship,” known today as the Red Meeting House and St. Thomas' Episcopal Church. Amenia is the town you’d want to retire in or go to for a quiet weekend holiday; houses are classy, the surrounding environment is clean, and Air is as fresh as it gets.

These small towns offer a vibe far apart from what New York City is known for, peace, nature, art, and calming experiences everyone looking for a weekend escape or a reset from fast-paced lifestyles and busy city life can enjoy. Most of these recommended small towns in NY are only a 1-2 hour drive out of Manhattan and can make a perfect overnight date spot or romantic escape thanks to their rich nature and artistic values. 

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