When many people think about New York, they automatically imagine New York City. However, there’s more to New York State than the Big Apple and Niagara Falls! We’ve gathered up some of the best small towns from around the state to help you discover the beauty of the Empire State from top to bottom!
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New York is home to a ton of great destinations ranging from tiny hamlets to the sprawling metropolis of New York City. There may even be so much on offer that you don’t know what to choose! Instead of reading website after website, let Let’s Roam do the planning for you! With hundreds of travel guides, destination scavenger hunts, and more, we’ve got your trip covered from A to Z!
Adorable Small Towns That You Don’t Want to Miss
Below you’ll find a list of the best small towns in New York you won’t want to miss. From idyllic hamlets along the Hudson River full of fascinating historic places to charming towns nestled in the mountains, these destinations are the perfect place for a romantic weekend getaway, a family vacation, or a girl’s weekend.
Upstate New York and the Hudson Valley
Broadly defined as the area lying north and northwest of NYC, Upstate New York features a slew of historic towns. Many of the people that live here commute back and forth to the city for work, giving the whole area a young professional vibe that you don’t find in many small towns.
This creatively-named town lies just a few hours by train away from New York City but feels like it could be on another planet. Hudson is home to just 6,000 people but attracts a bevy of urban artists. Thanks to the creative residents, the town has a surprisingly large array of oh-so-chic art galleries, treasure-trove antique shops, and welcoming cafes. Sometimes called the Brooklyn of the Hudson Valley, the town has a lot to offer culture vultures and history lovers.
Established at the end of the 18th century, the history of Hudson goes way back, and it’s proud to be the first city in the United States. Yes, the history buffs out there may be scratching your head at that one. Technically, it was the first city to be incorporated after the thirteen colonies joined together to form the United States. Thomas Jefferson and James Madison both visited Hudson in hopes of convincing local businessmen to start working more with French businesses instead of British ones.
Interestingly (at least for the Hamilton fans out there!), the editor of a Federalist paper based in Hudson published an article accusing Jefferson of paying a Washington D.C. newspaper to run libelous stories about his political opponents. After being found guilty in his first trial, the newspaper editor was defended by none other than Alexander Hamilton who gave a closing argument that lasted six hours. Sadly, the verdict wasn’t overturned, but it did lead to a law protecting the freedom of the press.
Just a short train ride north from New York City in Westchester County, Tarrytown is nestled alongside the Hudson River. With a population of just 12,000 people, the town feels more like a village than a suburb of New York. The woodsy slope that leads down to the glistening river is dotted with tightly-packed Victorian-style houses and small apartment buildings.
Meanwhile, the main drag of town is lined with mom-and-pop stores, coffee shops, restaurants, and bars. Like many of the commuter towns of New York and New Jersey, Tarrytown looks like it’s straight out of a Norman Rockwell painting. It has managed to attract many young families who left the city looking for more space and it is a great family-friendly destination.
3. Sleepy Hollow
Located just a few miles from Tarrytown in the Hudson Valley, Sleepy Hollow may not be home to the Headless Horseman as Washington Irving suggested, but it has a lot more to offer than that! Besides being the backdrop for a rather grim book, Sleepy Hollow has a quaint main street lined with historic buildings and endless natural beauty. The area is so lovely that even the famed Rockefellers decided to build a home there!
As you can probably imagine, many of the highlights of a trip to Sleepy Hollow are based on this celebrated book. The best place to start your visit is the lovely Beekman Avenue where many of the town’s most beloved restaurants, cafes, shops, and galleries are located. From there, you can check out the Sleepy Hollow Cemetery which is the final resting place of notable figures including William Rockefeller, Walter Chrysler, Andrew Carnegie, and Washington Irving. The cemetery is brimming with ornate sculptures, grand mausoleums, and the iconic Old Dutch Church. As you wander around the cemetery’s 85 acres, you can admire the stunning vistas of the Hudson River.
Another must-see spot in Sleepy Hollow is Kykuit Estate. Built by the Rockefellers, New York’s equivalent to royalty, the estate was built in 1913 and was home to four generations of the family. The main building rises six stories above the rolling hills, offering sweeping river views. Each of the rooms is richly decorated in the family’s timeless style while the basement houses Rockefeller’s private art collection which includes works by Picasso, Henry Moore, and Andy Warhol. Guided tours are available from Friday to Sunday during the summer and from Wednesday to Monday in the fall.
4. Saratoga Springs
Lying just south of Adirondack Park, Saratoga Springs is full of Victorian homes, picture-perfect streets, and a whole host of interesting museums. Meanwhile, the bustling main street features oodles of historic buildings housing restaurants, cafes, and bars. Saratoga Springs is most commonly associated with the Saratoga Race Course which boasts a full racing schedule during the summer months as well as its farmer’s market which is considered to be one of the best in the state.
The town is also situated close to the Saratoga Spa State Park. Originally built in the early 1900s, the spa was designed to help people reap the benefits of Saratoga’s mineral water. Believed to be high in healing powers, spas and health centers were built all around the region to help harness the tourism dollars that the water could bring. After more than 200 private wells were dug, New York State finally stepped in and started the Saratoga Spa State Park to try and preserve the mineral springs. You can see remnants of the park’s former life along the many miles of hiking trails that are perfect for walking, running, and hiking as well as two swimming pools.
Lying on the shore of Cayuga Lake halfway between NYC and Rochester, Aurora is another great New York college town. The town is home to Wells College, the alma mater of Pleasant Rowland who would go on to found the American Girl. Although Aurora was once simply another town, Rowland helped pave the way for the town’s resurgence.
Since then, many of Aurora’s 19th-century buildings including grand estates and tiny cottages have been converted into shops, restaurants, and guest houses. Many of these buildings are listed on the National Register of Historic Places and since many of them now offer luxurious accommodation options, you have the wonderful opportunity to spend the night in a historic building!
6. New Paltz
One of New York’s quintessential college towns, New Paltz boasts the State University of New York, a vibrant arts and culinary scene, and Historic Huguenot Street, a picturesque street brimming with 17th-century homes. The town is surrounded by the natural beauty of the Catskill Mountains and the Mohonk Preserve which is a haven for hikers, bikers, and runners thanks to its 70 miles of carriage roads and hiking trails.
One of the must-see attractions of New Paltz is the Mohonk Mountain House. This sprawling resort was founded in 1869 amongst 40,000 acres of lush forest. It started off as a humble resort for family and friends but quickly grew to the massive property you see today. The resort played a vital role in improving the living standards of Native American populations when it hosted a series of meetings and conferences in the latter half of the 19th century. The building is listed as a National Historic Landmark.
Just hearing the name Woodstock elicits sighs from hippies, wanna-be hippies, and music lovers of all ages. Although Woodstock wasn’t the actual home of the now legendary music festival (the nearby town of Bethel can claim that honor), it still pulls in the punters who love nothing more than good music, colorful houses, and a hearty splash of tie-dye.
Located within Catskill Park, Woodstock’s Tinker Street is THE place to go if you are looking for unique boutiques, vegetarian restaurants, and laid-back coffee shops. Besides giving visitors a great place to lay their heads after spending the day hiking or biking in Catskill Park, Woodstock is also near the Karma Triyana Dharmachakra Tibetan Buddhist Monastery. You can do tours of the idyllic monastery grounds during the weekend or join a meditation lesson.
Just hearing the name Woodstock elicits sighs from hippies, wanna-be hippies, and music lovers of all ages. Although Woodstock wasn’t the actual home of the now legendary music festival (the nearby town of Bethel can claim that honor), it still pulls in the punters who love nothing more than good music, colorful houses, and a hearty splash of tie-dye. Located within Catskill Park, Woodstock’s Tinker Street is THE place to go if you’re looking for unique boutiques, vegetarian restaurants, and laid-back coffee shops.
With more than 400 registered historical landmarks, the historic town of Rhinebeck is a fantastic year-round destination. Lying on the eastern bank of the Hudson River just a hop-skip-and-a-jump from Woodstock, this is one of the cultural hubs of the Hudson Valley with scores of galleries, performing arts venues, and museums. There’s also a wide range of cuisines on offer at the town’s mouthwatering restaurants and more than 40 specialty shops in case you are in need of some retail therapy.
As you wander around the tree-lined streets of the town, you can enjoy the sweeping views of the Catskill Mountains in the distance. If you can’t resist the temptation to put on your hiking shoes, miles of hiking trails await just outside of town.
9. Cold Spring
Cold Spring is one of the first destinations that New Yorkers stop at when they are searching for a bit of relaxation. Perched along the bank of the Hudson River, Cold Spring boasts gorgeous 19th-century buildings and a sea of different water sports such as kayaking, fishing, swimming, and SUPing. After you have burnt some calories, you can refuel at one of the many restaurants in the historic downtown.
One of the best parts about visiting Cold Spring is that it lies just an hour north of Grand Central Station. This makes it the perfect day trip for anyone who wants to explore the Hudson Valley but is a little short on time.
10. Long Island
Located just east of the New York borough of Queens, Long Island is famous for its string of charming beach towns known as The Hamptons. This is where the who’s who of Manhattan go for some fun in the sun. While the houses there are known to cost a small fortune, you can easily visit the area on a day trip from the city via the Hampton Jitney.
Lying on the far eastern end of Long Island, Montauk is one of the many beautiful towns that make up the Hamptons. Home to Hollywood A-listers such as Robert De Niro, Jerry Seinfeld, Neil Patrick Harris, and Beyonce, it also has earned the dubious title of being the most expensive beach to visit in the U.S.
Once you get over the sticker shock of being there, one of the highlights of a trip there is the iconic red and white Montauk Point Lighthouse located in the Montauk Point State Park. Constructed in 1797, this was the first lighthouse to be built in New York and the fourth oldest operating lighthouse in the country. It was also one of the first public works projects in the United States. It is now listed on the National Register of Historic Places and is a National Historic Landmark.
Montauk also provides a great base to explore the Hither Hills State Park. With its two-mile-long sandy ocean beach, sprawling campground, scenic picnic areas, and a 40-acre freshwater lake, Hither Hills is a perfect place to spend the day with friends or family. Some of the many activities on offer include horseback riding, fishing, windsurfing, and biking.
As you may have already guessed by the name, Greenport is a historic seaport where whaling ships once dropped anchor after a period at sea. The port was founded at the end of the 1700s and by the mid 19th-century, thousands of fishermen, shipbuilders, and farmers lived in the area. In the early 20th century, it became a well-known oyster processing location, and perhaps much to the delight of the local townspeople, it was a thriving center for rum running during Prohibition.
Situated on Long Island’s North Fork, Greenport is now an idyllic lakeside town where you can watch sailboats glide by, go for a swim at a sandy beach, or try some farm-to-table food at one of the many restaurants. Unlike The Hamptons, its hoity-toity neighbor, Greenport has a laid-back vibe to it which feels welcoming to both New Yorkers and visitors from afar.
The Mountain Towns
New York State’s interior is interrupted by a series of small mountain chains dotted with picturesque lakes and some of the best small towns in the state. The Adirondacks and the Catskills are some of the most famous mountain chains in the eastern United States and when you get there, it’s not hard to see why!
1. Lake George
Surrounded by the beautiful Adirondack Mountains, Lake George is a charming little town lying abreast against its namesake lake. With Lake George shimming in the distance, the tree-lined streets offer visitors a plethora of options for eating, drinking, and shopping. If you prefer to be a bit more active during your weekend getaway, you can rent a boat or stand-up paddle board, go for a swim, hike through the emerald hills, or join one of the many whitewater rafting or horseback riding tours.
Lake George is often considered to be one of the cleanest lakes of its size in the world. If you love water sports, this is certainly the place to do it! You can also visit one of the historic amusement parks just outside of town or play mini-golf in a French and Indian War-era fort. This makes it a great family-friendly destination for people with kids of all ages.
2. Livingston Manor
Perched high in the Catskills, Livingston Manor is a tiny town with a big backyard! Although it is home to just 1,000 people, there’s a surprisingly large amount to do there and in the surrounding area. Visitors can try their angling skills at one of the world-class trout fishing streams, hike to beautiful waterfalls and ponds, or simply hang out at the many restaurants, breweries, and shops dotted all around town.
Livingston Manor also provides easy access to Catskills Park where you’ll find more than 100 mountain peaks and six major rivers. If you go into the park, make sure to keep an eye out for wildlife such as black bears and bald eagles.
3. Lake Placid
New York’s mecca for outdoor adventures, Lake Placid serves as a beacon for New York’s thrill seekers who want to escape the city and enjoy nature. The town is tucked away between the rolling Adirondack Mountains and its shimmering namesake lake. This small town was the location of the 1980 Winter Olympics which helped it develop an impressive array of accommodation and dining options.
Most visitors come to enjoy the amazing views, fresh mountain air, sandy beaches, and to take advantage of the many outdoor activities on offer. You can hike to waterfalls, grab some oars or a paddle and venture out onto the lake, or explore the area on two wheels.
Around the State
If that isn’t enough to make you want to explore the Empire State, here are a few more amazing places located in the northern sections of New York. These may be a bit further from the Big Apple than some of the other destinations on this list but we promise it will be worth the trip!
Home to Cornell University, Ithaca is a gorgeous college town nestled in New York’s Finger Lakes Region. Boasting picturesque brick buildings and leafy streets, Ithaca is as Ivy League as they come. The heart of the town is Ithaca Commons where you’ll find a wide variety of eateries, shops, bars, and cultural spaces.
If you love nature, head over to the Cornell Botanic Gardens or the Ithaca Falls, a multi-tiered waterfall that is said to be one of the best in the state. If you really, really love nature, then lace up your hiking boots and go for a hike through one of the nearby gorges that surround the town.
Ithaca is also located close to Cayuga Lake, the longest of the Finger Lakes. Here, you can go swimming, kayaking, fishing, or boating during the summer. If you don’t have your own kayak, don’t worry! You can easily rent one in Taughannock Falls State Park. If you prefer to let someone else do the hard work, you can always jump on one of the lake cruises. Lasting 1.2-2 hours, the cruises give you the full lake effect without having to get your feet wet!
Located along the border of Connecticut in the foothills of the Berkshires, Amenia means pleasant on the eye in Latin and it certainly lives up to this reputation! The landscape is dotted with pastures and woodlands where you can go horseback riding and biking. In fact, many visitors come for the Harlem Valley Rail Trail, a 26-mile paved route that passes directly through town.
While you are there, make sure to check out Troutbeck Resort. This uniquely-named hotel was built as a sprawling private estate in the 18th century and has served as everything from a country inn to a local tavern. The property attracted literary giants and luminaries like Henry Thoreau, Sinclair Lewis, Supreme Court Justice Thurgood Marshall, and Theodore Roosevelt and it was also the site of some pivotal meetings of the Civil Rights Movement. Although the original house burnt down in 1918, the feeling of grandeur and legacy of the resort is still very much present today.
Located on the edge of crystal-clear Skaneateles Lake in the Finger Lakes region, this tiny village offers beautiful Victoria and Greek Revival homes, a quaint downtown overflowing with unique shops and locally-owned restaurants. The vibe of the area couldn’t feel more relaxed, making this a great place to have a little R&R if you’ve gotten tired of big city life.
The highlight of any trip to Skaneateles is the glistening lake that beckons from the edge of town. This is a popular spot for boating, yachting, and fishing. There are lake cruises running throughout the summer or if you want to get even closer to the lake, you can go for a swim in its refreshing waters.
Calling all baseball fans! This is one place that you won’t want to miss. Situated about halfway in between Albany and Syracuse, Cooperstown’s claim to fame is that it is home to the National Baseball Hall of Fame and Museum. This interesting museum features more than 38,000 artifacts showcasing the history of baseball and honoring the players and coaches who dedicated their lives to America’s pastime.
If you aren’t a huge fan of baseball, there are still plenty of reasons to visit the town. The small-town charm combined with world-class attractions is sure to win you over. During your visit, you can check out Native American art at the Fenimore Art Museum, try a few tastings of refreshing craft beer at one of the local breweries while listening to live music, go for a stroll on one of the many hiking trails in Glimmerglass State Park, or simply enjoy sitting on the shore of Otsego Lake indulging in melt in your mouth ice cream.
Ready to roam?
Whether you’re looking for a weekend getaway or putting together a New York road trip, we hope this guide to the most beautiful towns in New York has put you in a New York state of mind! If you’d like to read more about all of the great things to do in New York, make sure to check out the Let’s Roam Explorer blog. Here, you’ll find hundreds of travel guides covering all corners of the state and beyond.
While you’re there, make sure to download the Let’s Roam app. This is the spot to access all of our awesome scavenger hunts. Not only do these hunts let you learn more about a destination, but we promise you’ll have a great time doing it!
Frequently Asked Questions
Some of the best small towns in New York include Ithaca, Hudson, Sleepy Hollow, and Saratoga Springs. All of these towns have a lot to offer visitors including historic sites, outdoor adventure, and more!
If you’re visiting New York City and want to visit a charming small town as a day trip, some of the best options include Tarrytown, Sleepy Hollow, Hudson, and Cold Spring.
If you want to have a weekend getaway from the Big Apple, check out the charming small towns of Lake George, Greenport, Woodstock, or Montauk!
Although the adorable small town of Woodstock may not have hosted the epic music festival, it offers a colorful main street full of interesting boutiques and fantastic eateries that make it worth the trip!
If you’re looking for a great small town on Long Island, look no further than the idyllic beach towns of Montauk or Greenport.