When it comes to planning a getaway, there’s something so captivating about heading to a small town in the middle of nowhere. Don’t get me wrong, I love New York City. I’m convinced of the benefits of an NYC staycation replete with cozy restaurants, museums for the kids, and some of the best spas. But as soon as I step off the island…BOOM. Peace. Calm. Nature. If you feel the same way, allow me to present ten of the most charming small towns in the Catskills, ranging from hippie history-making Woodstock to Livingston Manor and Greenville with its drive-in movie theater. So pack your suitcase, book your train ticket and beware, once you leave the big city, you may never want to go back.
10 Charming Small Towns in the Catskills
from Catskill to Woodstock and Haines Falls
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1. Hunter, NY
- Why We Love It: great ski town, food scene and outdoor activities
- Things to Do: skiing, hiking, Hunter Mountain Brewery
- Where to Stay: Fairlawn Inn (from $233/night); Modern Hunter Mountain Treehouse (from $935/night, sleeps 10); The Hunter Chalet (from $1,623/night, sleeps 16)
If Hunter is known for anything, it’s for its reputation as a ski town—and PureWow Editor-in-Chief Jillian Quint confirms that skiing on the eponymous mountain is a must. However, what you should really stick around for is the food. Quint recommends Prospect, the restaurant at Scribner’s Catskill Lodge, known for New American fare and an emphasis on locally-sourced ingredients. With a craft cocktail list, panoramic mountain views and a menu helmed by Michelin-starred chef Alejandro Reyes Herrera, it’s a prime fine dining establishment in the Catskills. Quint also vouches for Hunter Mountain Brewery, which serves 15 of its own brews on tap. It’s a perfect place to congregate after a day on the slopes or hiking Becker Hollow Trail.

2. Haines Falls, NY
- Why We Love It: quiet hamlet east of Tannersville, great for hiking, camping and fishing
- Things to Do: North South Lake Campground for hiking an fishing
- Where to Stay: Rosehaven Inn Bed and Breakfast (inquire for rates); Cozy Elka Park Home (from $314/night, sleeps 6); Haines Falls Cabin (from $195/night, sleeps 5)
If you love camping, consider a trip up to Haines Falls, a peaceful hamlet directly east of Tannersville. Quint says the town is “home to my absolute favorite lake and hiking/fishing spot in the Catskills: North South Lake Campground.” Don’t let the confusing directionless name of the lake hold you back. It’s an affordable spot to vacation, with a nightly fee of just $22. Should you prefer to just spend the day by the water, there are plenty of activities around, including beach access, a picnic pavilion, boat launch and fishing dock.
- Why We Love It: cute village, Victorian inn, great antiques
- Things to Do: Tannersville Antiques and Artisan Center, The Pantry on Main
- Where to Stay: Camelback Resort (from $198/night); Tannersville Main Street Lodge (from $202/night, sleeps 6); Downtown Tannersville Apartment (from $150/night, sleeps 4)
Tannersville is Haines Falls’ neighbor, and its crown jewel is Hotel Lilien, a Victorian inn that Quint says is a “must stay”, noting that despite the renovations, it “retains all the charm”.
PureWow Senior Commerce Editor Stephanie Maida alternately recommends Deer Mountain Inn. “It’s the most charming, rustic little getaway situated in the middle of the mountains,” she says. “Stone-walled fireplaces and antler chandeliers abound, as do incredible seasonal and local bites. I went in the winter (in the midst of a snowstorm), so I traded my hiking boots for snow shoes in order to explore the area (the hotel actually provides them!).” No matter the season, Maida says you must take a gander at the “short-but-vibrant Main Street dotted with restaurants and shops.” Stop at The Pantry on Main for breakfast and then spend the rest of the day antiquing to your heart’s content at Tannersville Antiques and Artisan Center.
- Why We Love It: small down delivering on the nostalgia
- Things to Do: Greenville Drive In
- Where to Stay: Sunny Hill Resort and Golf Course (inquire for rates); Glamping Yurt (from $143/night, sleeps 6); Catskill Skoolie (from $152/night, sleeps 4)
One thing I’m sure no human can resist? Nostalgia. From the resurgence of the 2010s to the fact that everyone’s walking around with a shaggy mullet, we can’t resist a blast from the past. Quint calls this charming small town in the Catskills “Home of the most authentic and fun drive-in movie theater I’ve ever been to.” Said Greenville Drive-In offers full concessions, drinks and programming that begins at dusk. This retro spot has been a community fixture since 1959, and the season runs from early May through Columbus Day.

5. Woodstock, NY
- Why We Love It: unique shops, artsy sensibility
- Things to Do: Levon Helm Studios, Ashokan Reservoir, Good Night
- Where to Stay: Twin Gables of Woodstock (from $175/night); Woodstock Serene Retreat (from $217/night, sleeps 4); Byrdcliffe Artist Studio (from $215/night, sleeps 2)
Yup, this is the *Woodstock* of musical lore—though the actual event took place about 40 miles outside the town on a dairy farm in Bethel. Even so, Quint says, “The whole town still has a really chill, artsy sensibility. There are so many fun shops to pop into, and I highly recommend driving a few minutes to take a walk along the Ashokan Reservoir.” There, you’ll find 5.5 miles of dams and plenty of fish. Quint also recommends seeing a show at Levon Helm Studios. The venue pays homage to The Band’s Levon Helm, whom Rolling Stone called “rock & roll’s greatest drummer.” Fittingly, Helm performed at Woodstock in what would later be described as a “wild” Midnight Ramble. The Studio originally began as a space for Helm’s musical collaborations, and today hosts myriad live music acts.
Pre- or post-show, consider stopping into Good Night for Southeast Asian cuisine and Early Terrible for a nightcap—Quint calls both “fabulous”.

6. Saugerties, NY
- Why We Love It: small-town vibes, diverse activities and deep history
- Things to Do: Saugerties Stallions baseball game, Saugerties Lighthouse, Seamon Park
- Where to Stay:AutoCamp Catskills (from $149/night); Modern Catskills Cabin (from $22/night, sleeps 4); Luxury A-Frame Cabin (from $296/night, sleeps 2)
Maybe hippie art and culture aren’t your vibe—no worries. Head over to Saugerties, a town that Quint notes is close to Woodstock, “but a world away in terms of vibe.” She describes Saugerties as having more of a small-town feel. Quint, our Catskills concierge, follows an itinerary that consists of a trip to the village beach for swimming and fishing, and then hitting up a Saugerties Stallions baseball game. Other fun activities include the Saugerties Lighthouse, built in 1869 that is now a bed and breakfast, and Seamon Park with its peaceful gardens.

7. Livingston Manor, NY
- Why We Love It: great shopping on Main Street, great food, drinks and entertainment
- Things to Do: Sunshine Colony, Catskill Brewery, Cabernet Frank’s
- Where to Stay: The Arnold House (inquire for rates); Livingston Manor Forest Cottage (from $161/night, sleeps 4); Parkston Schoolhouse (from $166/night, sleeps 4)
PureWow Vice President of News and Entertainment, Philip Mutz, had only good things to say about Livingston Manor, a hamlet about an hour west of Woodstock and Saugerties. Mutz enjoys perusing the local shops on Main Street. Highlights include Sunshine Colony, a suave bar specializing in natural wine, beer and cocktails, plus seasonal snacks. (Mutz recommends going for a glass of wine). For the beer die-hards, Mutz says Catskill Brewery is a must. The microbrewery and taproom is known for its wide variety of drinks, mixed fermentation and the Devil’s Path IPA, named for the region’s most difficult trail. Hungry? Mutz says you can’t go wrong with The Kaatskeller, where a big pizza pie will satisfy hungry stomachs. The last thing you should add to your itinerary: “Cabernet Frank's is a short drive and a must-visit for live music and a festive/fun night out.”

8. New Paltz, NY
- Why We Love It: larger town 1.5 hours from Manhattan, great mix of historic and outdoor activities
- Things to Do: Mohonk Preserve, Mohonk Mountain House, Huguenot Street
- Where to Stay:Moondance Ridge Bed & Breakfast (from $169/night); The 1772 Lefevre Stonehouse Suite (from $113/night, sleeps 3); Little Yellow Cottage (from $95/night, sleeps 3)
Depending on who you ask, New Paltz is in the Catskills…or it’s in the Hudson Valley. I say that if you’re wanting to get upstate but can’t venture too far (some of these villages are two or more hours from NYC), New Paltz is a good compromise, since the Mohonk Preserve is just south of the Catskill Mountains. And that counts for you busy New Yorker, right? If you want a luxe experience, book yourself into the all-inclusive (and historic) Mohonk Mountain House, but wherever you stay, you’ll have a great time. Outdoorsy types will want to beeline for Mohonk Preserve, whose many trails promise hours of outdoor delights. (Pro tip: Start at the Visitor Center and then use the East Trapps Connector Trailhead to access 100+ miles of trails.) In town, Huguenot Street features ten acres of beautifully preserved 17th-century homes, buildings and artifacts. There are guided tours and reenactments year round, with special and spooky programming in October.
9. Windham, NY
- Why We Love It: referred to as the “Gem of the Catskills,” lots of outdoor activities, great food scene
- Things to Do: walk Main Street for specialty shops and restaurants, Windham Golf Club, Windham Local Public House
- Where to Stay: Hotel Vienna (from $121/night); Windham Cabin Escape (from $153/night, sleeps 6); Alpine Chalet (from $175/night, sleeps 4)
The town of Windham was founded in 1798, making it one of the region’s most historic villages. Here, there’s something for everyone, from the foodie to the hiker and wine connoisseur. Starting with the food scene, there are two establishments that should be on your radar: Windham Local Public House and Millrock Restaurant. The former is an eclectic cafe dishing up Thai curry and dim sum alongside bagels, lox, coffee and wine. There’s also live music on Friday and Saturday nights. Meanwhile, Millrock is the local Italian joint, and you’ll find comfort classics such as baked clams, linguine and veal cutlet on the menu. If you’ve come upstate for the great outdoors, Windham Mountain Club has great skiing and snowshoeing, plus golf in milder seasons.

10. Catskill, NY
- Why We Love It: steeped in art history, on the banks of the Hudson
- Things to Do: Olana, Thomas Cole National Historic Sit, Hudson River Skywalk
- Where to Stay: Woodstock Way Hotel (from $305/night); Cozy Catskills Cabin (from $140/night, sleeps 4); Catskill Village Cottage (from $106/night, sleeps 2)
Yes, the Catskills is a region (and mountain range), but it’s also a singular town that boasts spectacular fall foliage. It sits on the banks of the Hudson River, and is home to the Hudson River Skywalk. The three-mile bridge connects the town’s major attractions, Thomas Cole National Historic Site (founder of the Hudson River School of American landscape painting) and Olana, the former home and studio of 19th-century painter Frederic Church.