The 16 Most Charming Small Towns in New York
If you’re anything like us, you’re itching to get away from the city right now. And while the CDC stresses that staying home is the best way to prevent the spread of COVID-19, the organization also lists advice for how to reduce your chances of getting sick if you do travel, including wearing a face mask and avoiding close contact with others. If you decide to leave town, consider checking out one of these beautiful spots (while following social distancing protocols, of course). They’re all within a few hours' driving distance of NYC and are brimming with idyllic charm, and in a lot of cases, more space to spread out. (And if you’re not planning to travel yet, may we suggest adding this list of small towns in New York to your bucket list so you can have something to look forward to next year?)
Note: There is currently a travel advisory in place for travelers to New York state. Per the state’s official website, any traveler to New York state must obtain a COVID-19 test within three days of departure, prior to arrival in New York. Upon arrival in New York, the traveler must quarantine for three days and on day 4 of their quarantine, they must obtain another COVID test. Find out more here.
1. SKANEATELES, NY
Skaneateles is one of those towns that feels like it’s straight out of a movie: There’s loveliness at every turn, with lots of historic and perfectly preserved detail. Plus, every shop, restaurant and viewpoint you stumble upon will be better than the next. Speaking of the view, our favorite place to sit and gaze out over the glittering lake of the same name is the waterfront Clift Park, with its adorable gazebo, and neighboring Skaneateles Pier. Once you’ve tired yourself out exploring the dense downtown, enjoy a wood-fired, artisanal pizza at Gilda’s, a favorite amongst visitors and locals alike that offers pick-up and outdoor seating.
Where to stay: Lakefront homes or those with unobstructed views are what most travelers seek in the Finger Lakes, regardless of season—this brand new two-bedroom apartment is only half a block from Seven President's beach.
2. Hudson, NY
This small city (about 6,400 people) is only a two-hour drive from Manhattan and a popular getaway, thanks in part to its mid-century antique shops and lively contemporary art scene. On Warren Street, Hudson’s main drag, is Grazin’, an old-school diner with yummy burgers that’s currently open and complying with state and local health and safety precautions. Also on Warren is Swoon Kitchenbar, an upscale brasserie available for takeout with an impressive wine list and delicious cocktails.
Where to stay: Take a deep breath and inhale all the fresh air when you stay at this 19th century townhouse that comes with a bountiful garden. Or, pick out the room that speaks to you and check in to the devilishly photographable new Maker Hotel, where the recently opened gym offering personal training and Pilates is currently open by appointment.
3. TIVOLI, NY
What Tivoli lacks in size, it makes up for in quality. The town has seen a renaissance in recent years, with hip new businesses making this approximately 1.5-square mile village popular with New Yorkers who stumble upon it. Case in point: The tiny mobile coffee house concept All That Java, a hipster-meets-traditional Irish pub with serious whisky selection; Traghaven, a very Instagrammable general store; and the oh-so-adorable inside (and out) of seasonal ice cream shop, Fortunes with its service window and yellow spiral staircase. You can also hike and kayak at Tivoli Bays or watch a performance at Kaatsbaan Cultural Park, where the 2021 schedule is forthcoming, but this year’s socially-distanced summer festival was a sold-out event.
Where to stay: Hotel Tivoli, at the corner of the town’s two main arteries, is hard to miss, thanks to its popular on-site The Corner restaurant, which boasts outdoor seating on a large wrap around porch. Owned by painters and set on three levels of a stately historic building, each of the 11 rooms here are completely unique and big on design and art, with some gawk-worthy rugs and lighting-fixtures. If you're looking for a small space for just you and your beau, this romantic luxury chalet for two is the way to go.
4. New Paltz, NY
You can make the 90-minute drive to New Paltz just to stay at the Mohonk Mountain House…we won’t judge. The all-inclusive Victorian-era hotel sits on 40,000 acres on the Shawangunk Ridge and has recently reopened with enhanced health and safety protocols. It looks like a castle and offers dozens of fun outdoor activities. New Paltz itself, now a college town, is one of the oldest towns in the U.S. with buildings dating back to the early 1700s. And, its age is a big part of its allure.
Where to stay: If the weather’s favorable and a night under the stars is more your style, check out this tent hosted by Tentrr, an accommodations group that partners with farmers, ranchers, and other property owners to offer unique outdoor stays on private land. If that's not your vibe, no worries. This cabin in the woods still makes for an ideal mountain getaway.
5. AURORA, NY
There are few things more pleasurable than taking a safe, socially distanced bike tour through this charming village and its main drag filled with historic buildings that line the eastern shore of Cayuga Lake. Mornings in Aurora are well spent taking in a coffee and the peaceful reflection of the lake, while days are best filled with local pottery or painting classes or at wine tastings at one of the many stops on the Cayuga Lake Wine Trail. Keep your tummy happy come the evening by enjoying an outdoor meal at a restaurant with innovative cuisine and cocktails like 1833 Kitchen & Bar or getting takeout from Fargo Bar & Grill.
Where to stay: The Inns of Aurora is not only *the* place to stay in Aurora, but in all of the Finger Lakes region. The collection of five masterfully restored homes, like the picture-perfect E.B. Morgan House, are spread out amongst Aurora and have become a unique part of the fabric of this town’s charm. You can also opt for a private house for you and your pals. This rustic log cabin retreat is located is centrally located on the Cayuga Wine Trail, with the Seneca Lake Wine Trail a short drive away.
6. Saugerties, NY
Saugerties is a quintessential Hudson Valley town. The village, on the west bank of the river at the mouth of the Esopus Creek, is a historic landmark with a main street full of buildings—antique stores, restaurants, mom-and-pop shops—preserved as their 19th-century selves. Spend the day at Opus 40, a sprawling outdoor sculpture park (currently open but with limited hours due to COVID-19 restrictions; guests in groups of five or less can also book guided tours in advance) or bring a bike to explore one of the many gorgeous bike trails.
Where to stay: Couples should book The Villa at Saugerties, a boutique B&B that design-minded folks will find both dreamy and romantic. With just a few rooms, it’s also a great option if you’re looking to keep a safer distance. Or, if you’re traveling with your family members or your chosen pod of friends, this Brick Cottage Retreat offers plenty of room.
7. Narrowsburg, NY
If you blink twice, you might miss this Sullivan County hamlet on the banks of the Delaware River. But that would be a shame, because its charming Main Street is packed with cool shops, like Maison Bergogne (just don’t forget to bring your mask in order to go in). The outdoor activities aren’t bad either: You can canoe or kayak down the Delaware or take a relaxing float from Skinner’s Falls with Lander’s River Trips. For lunch, order takeout from The Heron (and be sure to try the fried chicken). For dinner, The Laundrette is serving up their delicious wood-fired pizzas for takeout.
Where to stay: Across the street from the Delaware River and just a short walk to Narrowburg’s main street lies the Little House in the Flats. Also available to rent is this spacious lake house where you can let your hair down with ease.
8. Cold Spring, NY
You’ll feel completely transported in time in Cold Spring thanks to its 200-some preserved 19th-century buildings on the National Register of Historic Places. Visitors also make the trek to hike the surrounding Hudson Highlands. From the top of Breakneck Ridge, a challenging 3.7-mile loop, you’ll have some of the best views of the Hudson Valley.
Where to stay: The location of this beautiful home couldn't be any better. Though it's close to Bear Mountain and only two miles away from the Cold Spring Center, we hardly think you'll want to leave. It sits on an acre of gorgeous land and comes with a fire pit in front, two decks in back, and a backyard. Not forgetting a built-in movie theater.
9. RHINEBECK, NY
Rhinebeck gets a lot of love from travelers, and even boasts Presidential ties (former first-daughter Chelsea Clinton tied the knot here). Its popularity is deserved as the home to arguably many of the Hudson Valley’s finest restaurants, home décor, and antique shops and even a charming bookstore to discover your next great quarantine read. For $100 per person, you can fly in an old-timey 1929 New Standard D-25 at the Old Rhinebeck Aerodome, just outside of town, if you’re feeling adventurous and make a reservation ahead of time. Or plan a visit to Ferncliff Forest to climb “the tower” any time of the year; you can also mountain or fat bike here, camp, or just meditate in nature … whatever your outdoorsy heart desires.
Where to stay: Check out this breathtaking getaway house conveniently located close to all the great restaurants and shops of Rhinebeck Village, but secluded enough for you and your loved ones to be able to relax and lounge freely.
10. Beacon, NY
New York art lovers have been flocking to Beacon—just 60 miles from NYC—since 2003, when Dia:Beacon, a massive museum (the 300,000-square-foot space was once a Nabisco plant) home to contemporary and modern art, opened its doors and put this small Hudson Valley town on the map. At the moment, the museum is open to visitors by advance reservation with a timed ticket, but whether you’re able to snag one during the weekend or not, this beautiful upstate spot still has plenty to offer, including great food and beautiful Mount Beacon Park.
Where to stay: Our favorite place to stay in Beacon was also once a factory: The Roundhouse, on Fishkill Creek, is now a local landmark with a restaurant, event space and boutique hotel. Nonetheless, we wouldn't turn down a night in this stunning loft that was once an 1860s brick factory space.
11. Greenport, NY
Forget Napa: New Yorkers looking for a quick wine getaway should look no further than Long Island’s North Fork. The antithesis of its sibling on the south shore, the North Fork is more about wineries, farm stands, sailing and country roads than about the glitz and glam of the Hamptons. Greenport is its seaside center.
Where to stay: The monochrome palette of The Menhaden will suit every type of traveler, as will the gratis snacks and pastries—which are now being individually wrapped and sealed—available on each guest floor. This quaint little cottage is also a great option if you want to stick with your quarantine pod.
12. CROTON-ON-HUDSON, NY
This Hudson River village in Westchester is just a one-hour drive from the city, but will transport you to a completely different world (think: a beautiful arch bridge passing over a dam with gentle flowing water). At the popular Croton Gorge Park, outdoor exploration across 97 acres is a highlight, especially if there’s snow on the ground and you can cross-country ski. Though there’s less of a downtown in Croton-on-Hudson than some of the other spots featured on this list, this charmer still features hip eateries like Croton Tapsmith, a taproom offering cold brews from nearby Hudson Valley producers and locally sourced food options (available for takeout and outdoor seating), as well as Ocean House Oyster Bar & Grill, which is only doing takeout at the moment. And don’t miss Van Cortlandt Manor, the 18th-century stone house and brick ferry house of New York’s famous Van Cortlandt family (Note: Due to COVID-19, opening hours are subject to change.)
Where to stay: This cozy country cottage boasts the prime location. The four-bedroom home is close to Harriman State Park, Bear Mountain State Park and Muscoot Farm, which is great for the kiddos. The Abbey Inn and Spa, located in close by Peekskill, is another fine option—if only so you can brag to your friends that you stayed in a former convent afterwards.
13. CANANDAIGUA, NY
Seeing the dreamy Sonnenberg Gardens and Mansion in the flesh would be reason enough to make the drive to this town, which sits on one of the sleepier and decidedly posh-er of the Finger Lakes. The popular attraction is the former summer house of a wealthy New York City family with a Queen Anne-style mansion and nine, distinct formal gardens (our faves being the Japanese and Italian gardens). While it’s currently closed for the season, we’re looking forward to the orchid show in April. Other popular things to do: Taking a pontoon boat out on the lake, which visitors can rent for the day from Sutter’s Marina and drive themselves as long as they are 21+ and have a valid driver’s license. And while most New Yorkers wouldn’t think of driving upstate for authentic Mexican grub, you should not pass go without trying Rio Tomatlan while here; a robust menu aside, the restaurant which is currently open for limited indoor dining and takeout is some of the most inspired we’ve ever tried.
Where to stay: The coolest and newest kid in town, The Lake House on Canandaigua will not disappoint, thanks to a spread out dock filled with Adirondack chairs overlooking the lake, or the adjacent all-seasons outdoor hot tub and seasonal pool, plus plenty of fire pits to park in front of no matter which time of year you go. Or, you can opt Heron Cove Sanctuary which promises peace, privacy and breathtaking views.
14. Woodstock, NY
Drive just ten miles west of Saugerties and you’ll find Woodstock. (Both towns are about a two-hour drive from Manhattan and can easily be done in the same weekend.) The town may be best known for lending its name to the iconic music fest—which, fun fact, actually took place 60 miles away in Bethel—but it’s also home to a thriving art scene and has great hiking options nearby, like picturesque Kaaterskill Falls.
Where to stay: You can’t help but feel relaxed when strolling around this woodsy Woodstock hideaway overlooking the spectacular Tannery Brook waterfall.
15. SAG HARBOR, NY
Whether you love or loathe the Hamptons, one thing most New Yorkers can agree on is that the towns “Out East” including East Hampton, Southampton, and Amagansett are undoubtedly attractive. Still, the clear winner in our hearts is Sag Harbor, both for its adorable Main Street, but also for it’s more laid-back vibes and waterfront marinas, which you’re likely to spot as you take a stroll through the picturesque downtown. The popular Sag Harbor Whaling & Historical museum, housed in a meticulously-preserved mansion, celebrates the town’s whaling past and is open seasonally, but you can also visit it virtually for free anytime. Also on your Sag hit list, especially if shopping’s your thing: Loveshackfancy, a luxury lifestyle store and Jayson Home, a celebrated home décor shop.
Where to stay: With its own private pool, this picturesque home right in the village of Sag Harbor offers tons of natural light, plenty of privacy and has everything you’ll need for a relaxing stay.
16. KINGSTON, NY
Kingston, one of the Hudson Valley’s most popular and evolving towns that was the original capital of New York state, overflows with shopping sites sitting on not one, but two separate, picturesque main downtown streets. The artist enclave is a place you’ll find record and music stores, tattoo parlors, bookstores, and Outdated, a coffee-meets-antique shop housed under the same roof (currently open Wednesdays to Sundays for takeout). Architecture buffs will want to take a stroll through uptown Kingston’s Stockade district to see historical old stone houses, specifically at the picture-worthy four corners—the only intersection in the U.S. where these 18th century homes sit on all four corners. Characteristic of the neighborhood, visitors will also stumble upon charming streetlights and weathered blue stone sidewalks.
Where to stay: This lovely loft in a carriage house dating back to the 1930s is filled with well-curated rustic decor and architectural details such as rich, brown wainscoted walls, french doors and barn windows that bring in natural light.