Catskills Travel Guide: A Wintry Weekend Escape From NYC

Last updated: January 2020

Right in the backyard of New York City, the stunning natural beauty of the Catskills – secluded yet vast at the same time – truly makes it the perfect weekend escape. Whether you want to simply power down, relax and recharge or embark on a series of adrenaline-infused experiences (or a combination of both), this expansive wilderness has something to offer everyone, year-round. Here, our guide to enjoying this sprawling winter wonderland during the colder months, from breathtaking outdoor adventures to cozy fireside cocktails, scenic drives to going off-grid in that quintessential cabin in the woods.

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Starting at just a two hour’s drive upstate, the Catskills is comprised of a number of small towns and villages comprised of four regions: the Southern Catskills (Sullivan County), Eastern Catskills (Ulster County), Western Catskills (Delaware County), Northern Catskills (Greene County, also known as the place where Rip Van Winkle took his epic nap) and of course, the Catskill Mountains. They all offer unique experiences, stunning landscapes and their own quirky touches, ready to be explored by car in a matter of hours from end to end.

Yes, you will need a car. While there are some public transportation options available, they will only get you so far. Plan on arriving in your own set of wheels to thoroughly enjoy everything the Catskills has to offer – and in the winter, that does mean 4-wheel drive.

Unless you’re in town or staying at an equipped accommodation, wi-fi and cell reception throughout the Catskills is spotty at best, non-existent at most. Be prepared to power down and disconnect – it truly is the best way to experience the beauty of the Catskills. Can’t live without Google Maps? Tip: map out and download your destinations before your trip, which will still route you while offline.

Contrary to popular opinion, the Catskills town of Woodstock is not the home of the legendary 1960s music festival. (That actually took place in Bethel, about an hour and a half southwest.) However, you can still expect a laid back, artsy and yes – hippie vibe throughout this bohemian town.


From hidden cabins in the woods to hip boutique hotels to rustic-chic mountain lodges, the Catskills offers accommodations to suit every taste – and budget. Our picks:

Airbnb I All Catskills 

You’ll find numerous options available all throughout the Catskills on Airbnb, however we thoroughly enjoyed our stay at Kelley’s cozy, Hunter Mountain cabin (Northern Catskills). A wood stove with all of the fixings for s’mores, an oversized jacuzzi bathtub with beautiful view of the woods and a mellow, comes-with-the-house cat named Ruby (who won over even the non-cat people in our group) are just some of the things that made this house so special – not to mention proximity to a number of neighboring towns, restaurants and activities.

Hotel Dylan I Eastern Catskills

Situated right off Route 28 (the main highway of the Catskills) 10 miles outside of Woodstock, this hip boutique motel with the tagline “Peace, Love, Stay” features throwback, music-themed decor, bathrooms stocked with C.O. Bigelow products, and nightly, communal bonfires connecting fellow guests. Plus: free wi-fi and access to an on-site gym, restaurant/bar and seasonal outdoor pool.

Deer Mountain Inn I Northern Catskills

This rustic-chic lodge nestled in the hills above Tannersville, the Painted Village in the Sky, boasts six luxury-appointed guest rooms (some with fireplaces and balconies), two cottages accommodating larger groups, and a cozy-yet-lively on-site restaurant and bar. What Catskills dreams are made of, the three-story retreat also plays host to movie nights on the lawn (seasonal), evening bonfires and of course – stunning mountain views.

The Graham & Co I Eastern Catskills

Rustic Americana defined, this twenty-room hideaway in Phoenicia takes inspiration from the classic heritage of the Catskills mixed with a stylish, contemporary vibe. Expect thoughtfully appointed rooms alongside three acres of (seasonal) activities including an outdoor pool, hammocks for lounging, a badminton court, fire pit and picnic area. Bonus: free bikes for exploring the surrounding countryside at your leisure.


From robust farm-to-table dining to hearty diners to craft cocktails, there’s no shortage of options making up the Catskills’ thriving culinary scene. Our picks:

Deer Mountain Inn I Northern Catskills

While we didn’t stay at the Deer Mountain Inn (Tannersville), we did experience the equally beautiful, and delicious, on-site restaurant. Overflowing with rustic charm, savory dishes sourced from local farms are complemented by an extensive wine list, craft cocktails and drool-worthy desserts. The lodge-themed space also features large fireplaces, plush couches and taxidermied walls, plus a separate bar area that’s so cozy you may never want to leave. This place gets packed, so reservations are highly recommended.

Deer Mountain Inn, Tannersville I Catskills Travel Guide: A Wintry Weekend Escape From NYC I Traveling Lamas

Selena’s Diner I Northern Catskills

This no-frills roadside diner off Route 23A in Haines Falls is your perfect pitstop whether you want breakfast (served all day), a quick lunch, or an all-you-can-eat pasta dinner (served every Wednesday night). Expect friendly service, huge portions and affordable prices at this local landmark just minutes from Hunter Mountain – the perfect place to refuel aprés ski. Don’t feel like leaving your cozy cabin-in-the-woods? Fret not. They also deliver.

Selena's Diner, Tannersville I Catskills Travel Guide: A Wintry Weekend Escape From NYC I Traveling Lamas

Peekamoose Restaurant & Tap Room I Eastern Catskills 

This lively tavern off Route 28 in Big Indian is known as the Gramercy Tavern of the Catskills, and for good reason. Brooklyn-born chef Devin Mills cut his teeth at the famed spot in NYC (among many others) before moving closer to the farms that supplied his menu in 2004. Alongside his wife Marybeth, the pair now offer a fine dining experience sans-pretense, in a beautifully restored country farmhouse. Expect the freshest farm-to-table ingredients, a daily changing menu and an ever-present patio bonfire stocked with marshmallows and bamboo sticks. The place has generated a loyal following of locals and visitors alike, so you’ll definitely want to call ahead to make that reservation.

Phoenicia Diner I Eastern Catskills

Also off Route 28, (about 10 miles east of Peekamoose) this hip hotspot offers traditional breakfast and lunch diner favorites with a contemporary twist, using local ingredients sourced from Catskills and Hudson Valley farms. (Sorry dinner diner fans, they close at 5pm.) The refurbished roadside eatery presents the perfect blend of retro diner charm with rustic mountain touches, not to mention heaping portions and a full bar. Busy at any time of day and especially packed for weekend brunch, reservations aren’t accepted – so show up early and expect a wait amongst the rest of the locals, visitors and hicksters also vying for a table.

Shindig I Eastern Catskills

Located in the heart of Woodstock, this laid-back resto serves up casual comfort food upgraded to suit contemporary tastes. Think unique takes on buttermilk biscuits, farm fresh eggs, mac n’ cheese, burgers and southern ‘fried’ chicken, even warm cookies served with milk and seasonal pies. The cozy spot seats just 30 and doesn’t take reservations, but they’ll take down your phone number and call you when your table’s ready – so you can tinker around town in the meantime.


Hike Kaaterskill Falls I Northern Catskills 

This popular hike offers a short (but steep) trek to a 260-foot cascading waterfall, divided over two drops. The up-and-back hike spans two miles in total taking about 1.5 hours, appropriate for most hiking levels. If you’re feeling extra adventurous you can also climb the steep staircase next to the base of the falls for a higher view point, but BE CAREFUL. The stairs are heavily eroded and slippery (especially after rain or snow), and hikers venturing beyond must do so with extreme caution…some haven’t been so lucky to make it out.

Hike Overlook Mountain I Eastern Catskills 

This 5 mile up-and-back hike may seem like an endless journey on the way up, but the views at the top are well worth it once you reach the summit. You know you’re getting close once you reach the ruins of the Overlook Mountain House, a 1930s hotel that never finished completion. Once at the top, you can climb a Fire Tower to the reward of breathtaking, 360-degree views, and/or you can head over to the nearby cliff overlook for equally stunning vistas. Set aside at least 3 hours and warning! A difficult hike already in good weather, this becomes a much more difficult climb in snow. Appropriate attire and hiking boots are a must if you want to make it to the top amongst the elements.

Ski I Eastern, Western + Northern Catskills

Ski bunnies have no shortage of options all throughout the Catskills, from Hunter and Windham Mountains in the North to Plattekill Mountain in the West to Belleayre Ski Center in the East – the latter boasting the highest skiable peak in the Catskills and one of the only resorts offering snowcat skiing in the region. There are plenty of options for cross-country skiing, snowmobiling and snow tubing as well, and don’t forget to check with your hotel for discounts on lift tickets.

Spa I Eastern Catskills

After exerting all that energy, you’re going to be in need of some serious R&R. At the award-winning Emerson Resort & Spa in Mount Tremper, treat yourself to soothing holistic treatments ranging from facials to massages to mani/pedis and more, plus enjoy full use of the spa’s Relaxation Room, Quiet Room, Sauna, Steam Room and outdoor Pool and Hot Tub (seasonal). Still have more energy to burn? You can also use the resort’s fitness center and yoga studio. For inquiring minds: the resort was named for the poet and essayist Ralph Waldo Emerson, whose essay “Nature” inspired the development and protection of the Catskill Forest Preserve (extending a massive 450 square miles in total) which surrounds the Emerson grounds.

Experience the World’s Largest Kaleidoscope I Eastern Catskills

After rejuvenating at the spa, head over to the neighboring Emerson Country Store (formerly the site’s 19th century dairy barn), where you’ll find a number of boutique shops alongside the world’s largest kaleidoscope. Seriously – it’s Certified by the Guinness Book of World Records. Completed in 1996, the giant kaleidoscope was originally designed by award-winning kaleidoscope artist Charles Karadimos alongside ’60s psychedelic artist Isaac Abrams and his son, Raphael. After entering through a fanciful kaleidoscope gift shop, you’ll emerge into a 56-foot tall silo-turned-immersive theater experience showing a 10 minute “Kaleidoshow” that changes from season to season. On deck during our visit was a new show called “Stardust,” a mesmerizing experience which we felt was well worth the $5.00 per person admission fee.

Drive I All Catskills

Discover roads less traveled with one of many scenic drives throughout the Catskills. Expect winding roads, bucolic countryside scenery, jaw-dropping mountain vistas, covered bridges and roadside real estate past and present. Get lost with a road trip playlist (synced for offline use, of course) and you’ve got yourself the perfect no-plans afternoon.

Star Gaze I All Catskills 

In-between breathing in the fresh mountain air, don’t forget to take a minute to look up – specifically when the sun goes down, when the night sky puts on a spectacular show of endless star-gazing.

Star gazing in the Catskill Mountains I Photo credit Alberto Lama for {un}covered I Catskills Travel Guide: A Wintry Weekend Escape From NYC

*All photos in this post by yours truly, @travelinglamas