Find Your Perfect Little Oasis Among These New York Small Towns
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Ah, New York, New York. As they say, a city so nice, they named it twice! But what happens when you want to venture outside that Big Apple and into the rest of New York? State, that is.
Well, the Empire State has plenty to offer.
Upstate and into the Hudson Valley, which wraps around the Hudson River, New York is a big, beautiful, rural landscape, complete with winding roads, rolling fields, and waterfalls galore—and all the idyllic towns that lie in between. Go for strolls down main streets, visit museums, peruse antique shops, explore hiking trails, go horseback riding, and more.
Out east, there's Long Island—home to Montauk, the Hamptons, and all the beaches and vineyards a summer vacationer could ask for. There, you have chic, luxe hotels, award-winning restaurants, water sports, world-class wine—and the sand between your toes. Venture to the very tip, and they say you've reached the "end of the world." Staring out from Montauk Point Lighthouse, you might just believe it. (Serenity found!)
Where will you find your oasis? Without further ado, we present 41 of our favorite small, charming towns (and picturesque villages, hamlets, and even one small, sweet city) in New York State.
Schenectady
Just a stone's throw from Albany, Schenectady boasts a bustling main street, complete with classic architecture and a well-preserved street clock. But perhaps its loveliest place for a stroll would be the Central Park Rose Garden, which features 4,000 rose bushes, a tiered fountain, and even a babbling brook. (Fun fact: Schenectady is where 2012's The Place Beyond the Pines, starring the now-married Ryan Gosling and Eva Mendes, was filmed.)
Saranac Lake
Visit this village among the Adirondack Mountains for the "cute cottage" architecture of the houses that surround the lake and the 1.1-mile Moose Pond Trail. Bonus: It's smooth enough to hike with kids.
Corning
As it's placed snugly in the Finger Lakes' wine country, Corning is, of course, a great place for a fine beverage. But our favorite reason to visit is the Corning Museum of Glass. The chic space covers more than 3,500 years of glassmaking history, and you can even watch glassblowers at work and design a glass ornament of your own.
Cooperstown
You know Cooperstown as the home of the National Baseball Hall of Fame—and indeed, the Hall's annual Induction Weekend is the town's biggest event. But there's so much more to see and do here. Take in art (at the Fenimore Art Museum) or music (at the Glimmerglass Opera), antique, golf, and even horseback ride. As for where to stay, may we recommend the Otesaga Resort Hotel—an old-school stunner that just so happens to be on the National Register for Historic Places—or the charming Victorian Inn at Cooperstown, pictured here.
Watkins Glen
In Watkins Glen, choose your adventure! In one direction, explore the Seneca Lake Wine Trail, known for its diverse lineup of world-class wines. In the other, visit the Watkins Glen State Park, where you'll find no fewer than 19 waterfalls. (The Gorge Trail, which lines Glen Creek, is known to be particularly easy on the eyes.) And don't miss the colorful Seneca Harbor Park Pier, pictured here, of course.
New Paltz
If you're headed here, one of the Catskills' prettiest locales, it's fair to suspect you're also headed to Mohonk Mountain House. A resort founded by the Smiley Family in 1869, the Victorian castle sits right on the water—which is why so many hop in a kayak as soon as they step outside. Surrounded by so much natural beauty, many choose to hike, but you can also treat yourself to an afternoon tea or a trip to the spa. Don't forget the nearby Historic Huguenot Street, with history preserved from as far back as the mid-17th century, when the area was known as "New Netherland."
Beacon
Only 90 minutes north of New York City, Beacon is known for its beautifully preserved Victorian homes, as well as its quaint Main Street, filled with shops, restaurants, and art galleries. But no trip is complete without a visit to its enormous contemporary art museum, Dia Beacon. Not only does it feature art and installations from some of the modern greats, including Louise Bourgeois and Michael Heizer, but it also has some very famous fans: BTS' art-loving leader, RM, filmed a concert for his debut solo album, Indigo, inside.
Lake Placid
Lake Placid is the winter sports destination, even hosting the Winter Olympics in both 1932 and 1980. But if, unlike a certain animated ice queen, the cold does bother you, there are also plenty of pretty shops and restaurants you can stay warm in. As you can see, it's absolutely stunning in the fall too.
Woodstock
Despite the fact that Woodstock—the iconic music and art fair of the '60s—was not actually held in Woodstock, the town has always been considered a home for the artistically inclined (back in the day, you could easily bump into Jimi Hendrix and Bob Dylan). No surprise, then, that if you visit Woodstock's town center, you'll find music shops and art galleries galore.
Pleasantville, New York
With its pristine downtown—complete with an oversized gazebo, the Pleasantville Diner, The Village Bookstore, and more—you'd be forgiven for mistaking Pleasantville for the set of Gilmore Girls. But this real-world beaut is actually a bit more modern. Look no further than the Jacob Burns Film Center for proof. The five-screen, art-house theater plays films from around the world, while hosting same of the biggest names in cinema: Jason Reitman, Jon Stewart, Ryan Gosling, Anjelica Huston, and Meryl Streep have all come to speak. The town's also less than a 10-minute drive to Blue Hill Stone Barns, arguably the culinary experience of the Hudson Valley, complete with its own highly innovative farm.
Aurora
The idyllic village of Aurora sits on Cayuga Lake in the Finger Lakes region. About 700 residents live in the town, and it is also home to Wells College. Plan your stay at The Inns of Aurora, with its impeccable accommodations and delicious dining options, plus activities like archery, kayaking, or touring local wineries. You'll want to spend a full day luxuriating at the spa.
Rhinebeck
If you love your little, quaint towns with a dash of luxury—particularly in the form of a lush stay—Rhinebeck is for you. Its tree-lined high street is chock-full of speciality shops—including Samuel's Sweet Shop, a classic candy shop owned by none other than actors Paul Rudd, Jeffrey Dean Morgan, and Hilarie Burton. (Fingers crossed for a sighting!) Once your sweet tooth gets its fix, head back to one of the prettiest hotels in the area: the Parisian-inspired Mirbeau Inn & Spa.
Sleepy Hollow, New York
Yes, we're talking about the Sleepy Hollow! The village is, of course, the setting of Washington Irving's "The Legend of Sleepy Hollow," aka the tale of the Headless Horseman. Naturally, such a claim to fame comes alive around Halloween. A proper spooky visit includes haunted hayrides, cemetery tours, and yes, a stop by the Headless Horseman Statue.
Greenport
Historic Greenport Village looks like something out of a harborside fairytale. At The Haborfront Inn, the architecture is a nod to the waterfront boarding houses of yore (with very modern amenities, like a pool and private beach). And for a room with an ocean view and the most gorgeous sunset, Sound View Greenport can't be beat. The North Fork area is also home to the famed lavender field, Lavender by the Bay, wineries galore, and an antique carousel that kids will adore.
Andes, New York
Andes is truly small—with just over 1,000 residents to its name—but when it comes to charm, it goes big. There's a special focus on fresh ingredients at both the restaurants and the cideries, and the leaf-peeping in the fall, both in town and throughout the Catskills, is incomparable.
Bovina, New York
Bovina is one of upstate New York's historic dairy towns, but we don't quite come for the milk. We come for our favorite restaurant: The Brushland Eating House. The restaurant offers a single seating per night to encourage conversation, say owners Sara and Sohail Zandi. "We want it to feel warm, familiar, and friendly," says Sara. With can-lined walls and a piano in the window, they can consider that mission accomplished.
Saugerties
Here, you'll find eclectic antique stores, beloved vintage shops, and lots of quality restaurants. Our pick? The Red Onion, which not only has a lauded vegetarian-friendly menu, but also a Wine Spectator Award. Don't miss the Cantine Dam Falls—and if you love nature and art, you have to see Opus 40, a massive environment sculpture that Architectural Digest called "one of the largest and most beguiling works of art on the entire continent." Oh, and this lighthouse? It's also the sweetest little bed and breakfast.
Hudson
Nicknamed "The Friendly City," Hudson has just under 7,000 inhabitants, but that hasn't stopped it from taking over the Hudson Valley. Included on our list of the "Best Small Towns in the U.S.," Hudson has orchards, galleries, breweries, fine antique shopping (our go-to: Red Chair on Warren), and a brand-new boutique hotel called The Maker. And all with a perfect view of the river.
Montauk
Montauk is known by many Long Islanders as "The End"—and indeed, it is the easternmost part of the island (and, for that matter, New York State). Nevertheless, if you're new to Long Island's famed Hamptons, we'd argue that Montauk is actually a great place to begin. It's just as lovely as any other Hamptons village—one scenic bike ride to the Montauk Point Lighthouse will convince you of that—but it feels a bit more casual and cozy. If you're looking to kick it up a notch though, Gurney's Montauk Resort & Seawater Spa, with its private beach club and ocean-themed spa, will certainly do the trick.
Bridgehampton
While we love the slightly more casual feel throughout Montauk, we are certainly not opposed to the ever-chic Bridgehampton—most especially, their crowning jewel, Topping Rose House. The 19th-century estate splendidly maintains its historic architecture, but there are a few perfectly modern touches too, including a serene lap pool and a Jean-Georges restaurant (farm-to-table, of course).
Oyster Bay
There are so many meticulously maintained historic homes in Oyster Bay, Long Island, it's hard to keep track. But for us, there's one that's an absolute must-see: Coe Hall. The 65-room Tudor Revival is magnificent. The land it sits on is perhaps even more impressive: Planting Fields Arboretum State Historic Park was designed by the Olmstead Brothers—half of which, of course, also designed Manhattan's Central Park—and features 409 acres of whimsical greenhouses, formal gardens, and woodland paths.
Cold Spring, New York
With fewer than 5,000 inhabitants, Cold Spring is the true definition of a small town. But it's big on beauty. Candy-colored houses line the streets, and on its little strip of the Hudson River, you can even find a castle: Bannerman Castle. (Not something you see every day on this side of the pond!) Head north on Route 9D for about one mile and you'll find the entrance to Breakneck Ridge, a prime place for rock scrambling.
Saratoga Springs,
Saratoga Springs has something for everyone. You love architecture? Walk the tree-lined streets to see the Victorians. Looking to relax? The Lincoln Mineral Baths are the natural springs for you. Shopping? There's a bounty of boutiques. And of course, there's the Saratoga Race Course for world-class horse racing. (Kentucky, eat your heart out!)
Ocean Beach
Located on Fire Island, Ocean Beach is, as the name suggests, a proper beach town—but it's not only that. The Sunken Forest makes for the perfect family hike, while the Heckscher State Park is wonderful for spotting wildlife (or setting up a BBQ). But if you do want to stay as close to the water as possible, Fire Island Parasail offers parasailing and private boat tours.
Skaneateles
Tucked into the Finger Lakes region, Skaneateles Village overlooks the lake of the same name. There are waterfalls, nature trails, and vineyards to visit, but we must point out a second Mirbeau location: Mirbeau Inn & Spa Skaneateles, which is designed to look like a French country estate (complete with landscaped ponds that look straight out of Monet's Giverney).
Lake George
Lake George may have a king's name, but it's known as the "Queen of American Lakes"—and rightly so! It's home to two forts—Fort William Henry and Fort Ticonderoga, both open to the public—as well as New York's largest amusement park, Splashwater Kingdom. The recreation options are endless: There's parasailing, fishing, diving, jet skiing, golfing, mini golfing, and horseback riding, to name just a few. Plus, did we mention hiking? Make your way up to the top of Prospect Mountain and you'll have a panoramic view of the whole gorgeous scene.
Croton-on-Hudson
If you're visiting Sleepy Hollow for spooky season, you also need to visit its neighbor, Croton-on-Hudson. Aside from the majestic Croton Gorge Park you see here, the Westchester County village is home to one of the most spectacular seasonal sights: The Great Jack O'Lantern Blaze. (2022's display featured more than 7,000 jack-o'-lanterns, all carved by hand and built into the most fantastical shapes.)
Trumansburg
Trumansburg is a Finger Lakes village with barely 2,000 people to its name—and charm at every turn. The B&B enthusiast has many an option here, with our favorite being the Inn at Gothic Eves, a perfect blend of the old and new. (How badly do you want to sit for breakfast at this table?) The must-see attraction would be Taughannock Falls, with an easy and rewarding hike that's even doable for kids. And make sure to stop at the Overlook at Taughannock Visitor Center to take in the magnificent view from above.
Lewiston
As the closest small town to Niagara Falls, Lewiston comes with quite the view—and, of course, quite the history. To learn all about how Niagara's water helps fuel electricity (still the main source for the state of New York), there's no place better than the all-new Niagara Power Project Visitors Center.
Tarrytown, New York
Just 25 miles north of Manhattan, this quintessential Westchester village is complete with the historic Tarrytown Music Hall and a flower-adorned, cafe-filled main street. No trip is complete without a visit to historic Lyndhurst Mansion, one of America's finest Gothic Revival mansions. Once you've toured the house, art, and rose gardens, hop over to the Tarrytown House Estate, where you'll find one of our favorite restaurants in the Hudson Valley, helmed by James Beard-nominated Chef Dale Talde: Goosefeather.
Westfield
Everything you've ever wanted to know about Concord grapes can be learned in Westfield. Since 1897, when Dr. Welch built the world's first large grape juice plant here, it's been known as the "Grape Juice Capital of the World." And still today, Chautauqua County is the largest grape-growing county outside of California, with approximately 20,000 acres devoted to vineyards, which you can visit—and taste! Concord grapes become ripe in September, so schedule your trip for late summer.
Chester
If you're looking for an upstate escape where you just stay put in a stunning setting, Chester (and its Glenmere Mansion) is an excellent choice. On 150 acres that overlook the Catskill Mountains, Glenmere Mansion, a Relais & Chateaux beauty, gives the appearance of a Tuscan villa, complete with a pool, bocce courts, and spectacular gardens designed by America's first major female landscape architect, Beatrix Farrand. It's ultra-romantic—and only an hour north of the Big Apple.
Callicoon
Right on the edge of Sullivan County, bordering Pennsylvania, you'll find this sweet, small town steeped in history—and this scenic Stone Arch Bridge built in 1880. The Western Hotel, which opened in 1852, is—as a prime example of Victorian architecture—one of Callicoon's most famous landmarks. Rafter's Tavern is a restaurant, art gallery, and music venue, all in one—and there's also the Callicoon Theater, which first opened in 1948, Today, it still has retro appeal, enhanced by the fact that they not only play blockbusters, but old indie films too.
Narrowsburg
Perhaps the cutest fun fact we could share about this Catskills town we love is that its main street only stretches 528 feet—and it's home to only 269 residents. But it sure packs a punch. Grab coffee at Tusten Cup, peruse books at One Grand, and stock up on snacks at general store Narrowsburg Proper.
Sag Harbor
One of Long Island's finest, Sag Harbor is an old whaling town that has managed to maintain so much of its history. Perhaps it's unsurprising, then, that it has some of the best vintage shopping and antiquing on the island. (One shop, called Ruby Beets, is housed inside a historic silent movie theater.) It's also family-friendly: Kids will especially love the old-school toy store, the Wharf Shop. Before you leave, snap a photo by the historic Beebe Windmill.
Ithaca
Yes, technically speaking, Ithaca is a bit closer to a small city than a town. And yet, the home of Cornell University is quite quaint—especially its downtown area, called Ithaca Commons. It features brick buildings, stately steeples, lively bars, and even an arthouse cinema. But they don't call Ithaca the land of the "gorgeous gorges" for nothing. The Cascadilla Gorge Trail is located right in the center of the city—a welcome respite from the hustle and bustle of college life.
Phoenicia
Arts and antiques are the name of the game in Phoenicia, a hamlet of Shandaken in Ulster County. After just a 2.5-hour drive from the city, you can shop all the kitschy markets and country stores on its main streets before heading into the mountains for some tubing. Yes, tubing: Phoenicia is known as the "tubing capital of the world," so is it's a must. (You'll want to go to Esopus Creek, and no, it's not a lazy river!) You may want to time your visit with one of these two big Phoenician events: the International Festival of the Voice, in August, or the Shandaken Artist Studio Tour, in June.
Southampton
Southampton is one of the largest hamlets in the Hamptons, which means it's filled with all kinds of entertainment options. There's shopping, of course, on its pristinely kept Main Street, but there's also art (the Parrish Art Museum, which focuses on local artists), snacking (Sip 'n Soda, a classic '50s diner, has the best ice cream in town), and Coopers Beach (the only one that offers day passes for visitors).
Cutchogue
We've mentioned wine a couple of times on this list, but if you ask the experts, Cutchogue is the true heart of wine country. In a less than 10-mile radius, you'll find more than a dozen vineyards, wine cellars, and tasting rooms—not to mention some very cute B&Bs (with chickens out back, the Sunny Side Up Bed and Breakfast is particularly quaint), and the beautiful beach. If you're in the business of baking pies (or just enjoying fresh fruit), stop by Wickam's Fruit Farm, one of the largest farms on the North Fork.
High Falls
High Falls is another small upstate town with Hollywood ties: Not only is out home to a number of celebrities, including Mandy Patinkin and Aidan Quinn, but it was also the setting for Natalie Wood and Warren Beatty's 1961 film, Splendor in the Grass. Still, its true appeal lies in its local establishments: Ollie's Pizza, Woodstock Farm Sanctuary, and the Wired Gallery, to name a few.
Mattituck
Where the North and South Forks of Long Island split, you'll find Mattituck, a waterfront hamlet that features more of what we love about the area: historic architecture, posh vineyards, and a well-stocked downtown (with a main street adorably called Love Lane). But if you do nothing else, visit Harbes Family Farm. With over 30 years in the business, the family-friendly farm features a farmer's market, a six-acre "barnyard adventure" (with a chick observatory), mini tractors, a hedge maze—and, come fall, all the pumpkins and cider doughnuts your hands and stomach can hold.
Amenia
Since its founding, Amenia has been known for radical thought—abolitionists, transcendentalists, and even the group that eventually helped to birth the NAACP met here. Today, that spirit is carried on by the Wassaic Project, an institution with arts education, lectures, gallery showings, and films, not to mention an annual heavy metal festival held in a parking lot. If you're looking to simply stroll with your thoughts, you couldn't find a prettier place than Wethersfield Estate & Garden, which boasts 1,000 acres of classical garden majesty. And there's no place more peaceful to stay than Amenia's gem of a resort you see here: Troutbeck.
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