Did you know that there are upwards of a thousand small towns spread across New York state? Each of them with its own flavor and special features, there are so many places to choose from and explore depending on what you’re looking for.
After a lifetime of wandering the cute little NY villages and towns, I feel confident in passing along which ones are the absolute best.
Table of Contents
- 14 Best Towns in New York
- FAQs about Towns in New York
Disclosure: Travel Lemming is an independent reader-supported blog. You can support us by purchasing via the affiliate links on this page, which may earn us commissions. Thank you!
14 Best Towns in New York
Home of Cornell University, over 100 waterfalls, and the Finger Lakes wine country
Ithaca is a small town that’s embraced its gorgeous nature, like many of the towns in upstate New York.
It’s situated right next to the enormous Cayuga Lake in the heart of the Finger Lakes region. This area is home to gorges, state parks, and some of the best waterfalls in New York state. Specifically, I’d recommend stopping by Buttermilk Falls or Ithaca Falls.
Beyond the beautiful nature, Ithaca is known for being home to Cornell University and a whole bunch of history. It’s a laidback town with plenty of interesting spots to explore.
A hippie-dippie dreamland that built its reputation from the most famous festival of the ‘60s
Woodstock is probably the most universally recognizable name on this list. It’s steeped in infamy for its connotation with the world-famous ‘60s festivals, but the concert didn’t even take place in the little town.
Regardless, Woodstock is still one of the most charming small towns in NY. It’s also where I grew up!
This little Hudson Valley town is hardly more than a few blocks long, but it packs a punch. Along Main Street, you’ll find loads of artistic flare, local restaurants, quite a few bars, and lots of places to relax. In recent years, there’s been a huge problem with littering and disregard for the locals. When you visit, please respect the area.
A rock climbing hotspot in the Shawangunk Mountains with a surprisingly lively nightlife scene
If you’re looking for an escape into nature that’s still connected to the comforts of the real world, then New Paltz is the town for you.
It’s one of the best places to stay in New York because there are a bunch of accommodations and things to do. Particularly, New Paltz is a hub for outdoor adventures like rock climbing, biking, and kayaking. After building up an appetite, Main Course or Lola’s Cafe will surely satisfy your tastebuds.
At night, there are several bars in town that live it up well into the night. Alternatively, you can check out Robibero Winery or Kettleborough Cider House if you’re into a more low-key experience.
👉 Pro Tip: The best time to visit New Paltz is during the fall. The leaves start turning a million shades of reds and oranges, but it’s not super cold yet. If you’ve never experienced autumn in upstate New York, it’s incredible. However, this is the most popular time to visit. So, book early!
A quaint town filled with tasty restaurants and historic places only an hour from NYC
Cold Spring is a cute small town with lots of delicious places to eat and historical landmarks to see. It’s located right on the banks of the Hudson River, only a short hour-long drive from New York City. There’s plenty of kayaking and hiking in the area.
The town’s interesting historical buildings and landmarks make it a popular stop among history buffs, such as Bannerman Castle and the West Point Foundry Preserve. All in all, Cold Spring isn’t the place for partying the night away. But it’s great for a little easygoing relaxation.
An ideal weekend getaway with horse racing, resorts, and shopping
Saratoga Springs has a little more of a lively vibe than some of the other small towns around New York. It’s less than an hour north of Albany, the New York state capital.
The biggest attraction in the town by far is the Saratoga Racing Course where you can go to see horseback riding races. Of course, many people head over there to place their bets as well, but races only occur from mid-July to early September.
Saratoga Springs also has a pretty big resort called the Saratoga Casino Hotel. It’s complete with a casino, live music performances, and an array of restaurants to choose from. You can basically spend your entire time at the resort and enjoy a lot of the things that Saratoga Springs has to offer.
A multi-faceted city with loads of personality that was New York’s first state capital
Technically, Kingston is a city, not a town, but it still manages that intimate feel that charming towns cultivate.
Located on the west bank of the Hudson River, Kingston is an area that’s steeped in history. It was actually the state’s very first capital. A lot of the architecture around the city still has that Victorian feel.
Today, Kingston has definitely leaned into being more trendy. In uptown and along the Kingston waterfront, you’ll find endless upscale restaurants and happening bars to choose from. It’s not necessarily the escape into nature that you might get from going farther up into northern or western New York. However, it’s still close enough to all these places that it makes for an excellent home base.
A mecca for water activities like rafting, boating, waterskiing, parasailing, and more
Lake George is a sweet town that’s practically a paradise for anyone craving a little outdoor adventure. It’s one of the most popular nearby vacation spots for local upstate New Yorkers. There’s an abundance of accommodations, but there are also a bunch of places to camp if you prefer.
The biggest activity in Lake George is the lake. There’s tubbing, boating, kayaking, wakeboarding, parasailing, and much more. If there were ever any water sports or activities that you wanted to try, Lake George is the perfect place to do it. Alternatively, you can just relax on the sandy beaches.
If you’re more interested in history, check out Fort William Henry and its coinciding museum. Or, for breathtaking views, take a drive on Prospect Mountain Highway.
A charming, little town made famous for an 1800s legend about the Headless Horseman
Sleepy Hollow is a small town with an infamous story attached to it – The Legend of Sleepy Hollow. The legend tells the story of the headless horseman who was decapitated by a cannonball in battle.
There are still a bunch of spots around the area that honor its namesake. Like Sleepy Hollow Cemetery and the Headless Horseman Bridge. So, the best time to visit this New York town is around the Halloween season.
Besides celebrating all the lore around the town, Sleepy Hollow has a number of other non-legend-related things to do. Such as wandering the Rockefeller State Park Preserve and visiting the Sleepy Hollow Lighthouse.
👉Pro Tip: Sleepy Hollow takes the month of October very seriously. If you’re planning on visiting around that time, be sure to check out their events calendar for the month!
A local cultural hub with art galleries, performing art centers, museums, and historic buildings
Rhinebeck is one of my personal favorite small towns in New York. In the area, you’ll find some of the coolest historical museums in New York state. Like the Old Rhinebeck Aerodome and the Hudson River Maritime Museum.
The town also has a bunch of historical sites, such as the Wilderstein Historic Center and the Delameter House. Along with art galleries, independent film showings, performing arts centers, and way more.
👉 Pro Tip: Rhinebeck is home to a variety of tasty restaurants. My top recommendations would be Terrapin or Cinnamon Indian Cuisine.
The National Baseball Hall of Fame and Museum is just one fun thing to do in this cozy township
The big thing that everyone knows Cooperstown for is the National Baseball Hall of Fame, so it’s an obvious stop for baseball lovers. Even if you’re not the biggest fan of the national pastime, you can still have a blast in Cooperstown.
There are quite a few different museums to peruse, like the Fenimore Art Museum and The Farmers’ Museum. If you’re in the mood for a drink, there’s the Cooperstown Distillery and the Red Shed Brewery.
Plus, the area is surrounded by some stunning places around town for nature lovers. Otsego Lake is a beautiful spot for a boat tour, and nearby Glimmerglass park has a few lovely hikes.
Home to one of the most picturesque New York State Parks and a famous car racing track
The village of Watkins Glen is best known for the huge state park of the same name. The Watkins Glen State Park is probably the most famous park in the Finger Lakes Region. A visit to the state park will weave you through remarkable greenery with cliffs and waterfalls along the way.
Watkins Glen is also home to a world-renowned car racing track. It hosts the Formula One Grand Prix and other major races in the United States every year.
When you’re done exploring nature and racetracks, pop in for a glass at one of the wineries along the Seneca Lake Wine Trail.
A fishing village with incredible oysters and seafood nestled right on the Peconic River
Greenport is an easygoing town located on the northern fork of Long Island. There are a number of museums, pretty views, and enough wineries and breweries to get your drink on.
The thing that sets Greenport apart from other little NY towns is its location. It’s a seaside village that’s right next to all the action of the big apple. So, it’s very convenient to just take the train to Manhattan, yet distant enough to be calm.
Not only does the area grace visitors with beautiful marine views from all sides. It also has some absolutely delectable seafood. Specifically, you have to check out Little Creek Oyster Farm and Market if you’re in the area. It’s definitely a fun thing to do on Long Island!
A gorgeous lakeside vacation town with live music and year-round events in the Adirondack Mountains
Saranac Lake is a cozy town in the Adirondacks with a long-standing history as one of the most beloved towns in NY and the country in general. It was actually ranked as the 11th best small town in America back in the ‘90s. It’s still held onto that charm today.
You can find exciting, outdoorsy things to do in the town year-round. From live outdoor music shows in the summer to skiing and tubing at Mount Pisgah in the winter.
Saranac Lake also has a fantastic little local shopping scene. There are a bunch of local brands and antique stores that sell clothes and souvenirs to remember your time in town.
A two-time former host of the Olympics that totes awesome natural views and loads of outdoor activities
The village of Lake Placid was put on the map after hosting the Olympic Games – twice! You can still visit the Olympic Ski Jump Complex, which holds year-round training for bold athletes.
Today, it’s known for being a true hub for everything outdoors. If you’re a skier, you’ll definitely want to spend a day or two on the slopes at Whiteface Mountain. It’s the fifth-highest in the entire state.
Then, there are the summer activities. Even though the town itself is called Lake Placid, one of the main natural attractions is another waterfront called Mirror Lake. There is also a myriad of hiking trails throughout Mount Jo, the Brewster Peninsula Nature Trails, and other peaks throughout the area.
👉 Read Next: Best Places to Stay in New York City
FAQs about Towns in New York
How many towns are in New York?
There are 933 towns in New York state, each with its own unique charm and offerings.
What are the five cities of New York?
The five largest cities in New York by population are New York City, Buffalo, Rochester, Yonkers, and Syracuse. There are over 1,500 New York cities in total.
What is the best town in New York?
The best towns in New York include Woodstock, Lake Placid, New Paltz, Ithaca, and Watkins Glen.
You’ve made it through my list of the 15 best towns in New York! If you’re into the live music scene, don’t miss my guide to the 13 best music venues in NYC.
Enjoy the small towns in New York!
(Featured Image Credit: JWCohen / Shutterstock)
Help us help you travel better!
Your feedback really helps ...
What did you like about this post? Or how can we improve it to help you travel better?