Here in New York, there’s nothing we love more than boasting about our charming small towns – some of which you’ve probably never even heard of. They may be hiding in plain sight, but you’ll be impressed by how these delightful places that are absolutely filled with their own history, attractions, parks, and things to do. With so many stunning Empire State towns to choose from, it’s difficult not to make this list never-ending, but here are 11 of our favorite perfectly picturesque small towns in New York you’ll want to visit for a weekend or day trip adventure.

1. Cazenovia
Doug Kerr/Flickr
Joshua C./Yelp
Mostly known throughout our state as being the home to the wonderful Cazenovia College, this small town also has many other gems hiding within it! One of our favorite things to do in Cazenovia is to visit the perfectly picturesque Stone Quarry Hill Art Park. Pictured above you can see the popular installation "Stacks" by David Harper which you can find at the incredible art park. It's a beautiful destination for anyone who appreciates interactive art.
2. Sackets Harbor
rchappo2002/Flickr
You'll find an incredibly stunning town right along the waters of Lake Ontario in Jefferson County when you visit Sackets Harbor. It's filled with historic sites, great restaurants, and delicious breweries. From battlefield sites to museums and endless water based activities, you'll love discovering all that Sackets Harbor has to offer!
3. Naples
Visit Finger Lakes/Flickr
Rich Engelbrecht/Flickr
Found in Ontario County, the village of Naples has just over 2,500 residents. Home to the annual Naples Grape Festival, this area of New York is loved for its thirst quenching wine and flavorful grape pies! Looking to experience the more adventurous side of Naples? Take a day to explore the amazing Grimes Glen Park where you'll encounter gorgeous waterfalls and serene views.
4. Rhinebeck
Steve Guttman/Flickr
Steve Guttman/Flickr
Rhinebeck is notable for its location - tucked way inside Dutchess County and easily reachable to those living in the nearby areas of the Upstate region, New York City, Massachusetts and also Connecticut, it's an idea spot for a getaway. The home to many of your favorite celebrities, this area offers serene views of the Catskill Mountains with the upside of being close to the big city life.
5. Clayton
Robert S. Donovan/Flickr
Robert S. Donovan/Flickr
Up in Jefferson County along the shores of the St. Lawrence River, you'll find this wondrous town that will instantaneously relax you. Settled in the early 1800s, Clayton is also a short distance from New York's other popular areas of the Thousand Islands, Alexandria Bay and Cape Vincent!
6. Windham
Michael Kreho/Flickr

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Diana Robinson/Flickr
Generally known for its popular landmark Windham Mountain, a fantastic place to visit for skiing or even weddings, this town can be found in Greene County. With a population of just over 1,700 residents, this quaint town is filled with picturesque long roads, winding through the Catskill mountains. Often referred to as the "Gem of the Catskills," Windham has twice been the host of the World Cup Mountain Bike Race!
7. Hammondsport
A.D. Wheeler/The Explorographer
Brian Holland/Flickr
Located in Steuben County with a population of not even one thousand residents, you can find this beautiful town at the southern end of Keuka Lake. Known for being the "coolest small town in America", Hammondsport has become a popular place to visit over the years due to its award winning wines and history with developing sea planes. Pictured above you can also see the Annual Antique Boat Show which is held right in Hammondsport!
8. Fairport
Peter C in Toronto Canada/Flickr
Peter C in Toronto Canada/Flickr
One of our many amazing towns located along the Erie Canal, Fairport can be found just outside of Rochester in Monroe County. Donned the "Crown Jewel of the Erie Canal," this town is truly one of our most remarkable places to visit. It's hard to top the history you'll find here!
9. Ellicottville
Brampton Cyclist/Flickr
RLEVANS/Flickr
This small town can be found in Cattaraugus County and has a population of just over 1,500 residents. Over the years this town has become a favorite spot for ski enthusiasts to visit but its charming touch has remained intact by keeping strict zoning laws...which means you won't be finding any of your favorite franchise restaurants in this town!
10. Lewiston
ihrivera/Flickr
HoeHo/Flickr
One of the larger towns on our list, Lewiston holds a population of over 16,000 residents. Right outside Niagara Falls, you'll find this town which was formed in 1818 and was home to the last stop on the Underground Railroad. Home to several attractions such as the Artpark and the Hydroelectric Power Station, there's plenty of history to be learned from Lewiston!
11. Waterloo
Ben's photoblog/Flickr
Ben's photoblog/Flickr
This small town with a population of just over 5,000 residents can be found nestled between two of our favorite Finger Lakes, Cayuga and Seneca. You may have heard of this tiny town for it's known as being the birthplace of Memorial Day, but it also offers tons of adventurous activities for you to take on along the Seneca River!

Have you ever taken a trip to any of these towns? With views like these, it’s hard to pick just one as our favorite!

Some of the best towns in New York have remained hidden gems, and you won’t find crowds no matter when you visit. For more New York travel inspiration, read about 9 Underrated New York Towns That Deserve A Second Look.

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picturesque small towns in New York

Kim Magaraci | November 22, 2020

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Living in New York is like living in your very own paradise! You're never too far from a beach, mountain, or city, so there's truly something for everyone to enjoy. Every region has beautiful parks, charming towns, and unique, delicious cuisine.

What unique words and phrases do people in New York say?

In New York, you'll hear plenty of phrases and words that might make you do a double take. On Long Island (note - ON, not IN), you'll hear people tell you to go stand on line. On, not In. Of course, our accent makes saying things like "cawfee" and "chawklate" common, and we eat Texas Hots, Garbage Plates, and Beef on Weck.

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Featured Addresses
Cazenovia, NY 13035, USA
Sackets Harbor, NY 13685, USA
Naples, NY 14512, USA
Rhinebeck, NY, USA
Clayton, NY 13624, USA
Windham, NY 12496, USA
Waterloo, NY 13165, USA
Lewiston, NY 14092, USA
Hammondsport, NY 14840, USA
Ellicottville, NY 14731, USA
Fairport, NY 14450, USA