The Perfect Itinerary for a Winter Getaway In the Catskills

It’s the winter and you want to get out of town. The brief: You, your nearest and dearest, crackling fire places (or evening bonfires), a cute mountain town (or ten), and a beautiful blanket of untouched snow. Well, folks, do you hear the Yiddish Alps calling? More specifically, Sullivan County’s Catskill Mountains are ready to reinvigorate your mind, body, and spirit. Located about two hours from Manhattan, it’s time to look forward to the perfect wintry escape in hilly hamlets like no other. In the wise words of Midge Maisel: “We’re going to the Catskills!”

Located in the sleepy town of Neversink, this cozy hotel it’s all the Aspen, with none of the fuss or fancy outfits required. Housed at a former new age wellness resort, the Foster Supply Hospitality boutique property is the perfect home base for your crew thanks to spacious rooms and suites (some with patios overlooking the peaks), all handsomely appointed and sans TV to remind you to disconnect from technology for a while and whittle down your reading pile. There’s even a cute bag for your phone imploring guests to give your phone a break, just like yourself.

Cold weather amenities include a gorgeous indoor pool and hot tub, otherworldly spa (ask for Gina or Dee, and book a massage or the fantastic Catskill Clay Wrap, where you’ll get exfoliated, wrapped in magic mud, and gently massaged throughout), yoga pavilion complete with a hearth and oversized windows, a fitness center with Nohrd equipment, and a crafting studio. Speaking of arts and crafts, when it's just too cold outside, you and your pals can make, say, a wreath with local trees or take a knitting lesson. Or, swap crafternoon for a yoga nidra class with yogi extraordinaire Kelly and/or her signature sunrise stretch class. Or, just sit by the fire with a cup of tea and a good book in the main house.

Hungry? The on-site restaurant, Bittersweet doles out plant-centric fare where on any given day you may feast on vegan queso with the crispiest tortilla chips you’ve ever had, a kale fennel Caesar salad, and chocolate mousse with amaranth (breakfast and lunch, as well as snacks throughout the day, are included for all guests).

Pro tip: Ask your waiter for a box of food scraps so you can take a short stroll to the barn and feed the property’s adorable goats. Does it get any cuter than this? We think not.

Skiers and snowboarders, perk up your ears and clamp on your gear. Holiday Mountain in Monticello is under new ownership and is one of the most affordable and best places to learn how to ski in the Northeast. Currently, the ski mountain has six ski trails of various difficulty from greens to black diamond, 12 snow tubing lanes, and a new learning center with a magic carpet lift. Day passes start at $55 and group lessons begin at $70 (or, try the beginner package: $185 gets you a lift ticket, rentals, and a one-and-a-half hour group lesson).

The ski resort is a few minutes away from Resorts World Catskills if you want to stop by for some fun at the slots or tables, an après-ski massage at the spa, or dinner at Cellaio, where the fresh pasta is divine — and well-earned after a day on the slopes.

Skiing isn’t for everyone — but that restorative mountain air is. If skiing or boarding isn’t for you, here are a few things worth experiencing outside. First up, snowshoeing with rentals from Fortress Bikes, which can accommodate groups of up to 15 people. (If you make the reservation on behalf of your group, request that your party pay you back for their share by Zelle®). Our favorite spot is the Hurleyville Rail Trail, the local sliver of the O&W railroad trail, but you can also ask the Hurleyville shop staffers for their best recommendations for local snowshoeing trails based on your crew’s preferences.

Before you leave Hurleyville for your adventures, or when you return, grab a bite at Forage and Gather Market & Café, where the smoothies and coffees are the energy boost you need (and Forage & Gather’s Mountaindale location has a full breakfast and lunch menu; the breakfast burrito hits the spot, as does the Casa or Greek wraps with falafel).

Winter hiking opportunities also abound in these parts. Get a lay of the land at Trailkeeper.org, a Sullivan County non-profit organization that provides clearly marked trail maps with a hike description, difficulty rating, and distance. If you’re staying at Hemlock Neversink, the property also has a slew of well-maintained trails with scenic mountain views, towering trees, and moss aplenty. Wherever you hike, be on the lookout for deer!

You can also BOLO for eagles at the Delaware Highlands Conservancy. On January and February weekends, the nonprofit runs a free program to feast your eyes on the incredible creature that is the bald eagle. After meeting at the visitor center, you’ll be transported to one of three locations where you can see the conservancy’s eagles roam free.

Last but not least, we’ll point nature-lovers towards ice fishing. Hire a local guide to take you out and about for trout-tracking, as these fish are in Sullivan County’s lakes and streams year-round. Cap off the day with a celebratory meal at The Arnold House in Livingston Manor as you retell the day’s adrenaline-pumping action, or perhaps with a cocktail at the property’s cozy-chic Frostfire Lodge. 

Keep your eyes peeled on The Cider Mill in North Branch. Currently, it's an eclectic boutique stocking local goods but a lot of exciting plans are in the works to add a tearoom, saunas, and more. The structure was erected in the 1940s and the spot has been vacant for the past 25 years before the ambitious new owners swept in. Speaking of new owners, The North Branch Inn down the block is also under new ownership, one of whom is the former chef from Brooklyn’s beloved French bistro Le Fond (so expect the food here to be pretty stellar).

A few minutes down the road takes you to the neighboring town of Jefersonville, also worth more than a quick calf stretch. At The Catskill Outdoorsman, you can enjoy the great indoors, too, with an indoor archery lesson at this veteran-owned and operated spot. We especially recommend swinging by for Glow Archery every Saturday night, a rollicking good time with music and various blacklight, balloon, and ping pong ball targets. (In addition to its indoor archery range, the outfitter also has all the gear you need for ice fishing, and for warmer weather months you can rent kayaks and stand-up paddle boards here).

Right next door you’ll find the recently unveiled Sullivan Sundries Market, occupied by chic coffee counter Bloom Coffee, a specialty foods market, a home goods/antique shop, and a soon-to-open wine shop. If you love antiquing, you’ll also want to visit The Vintage House. And since everyone loves sweets, Jeffersonville Bake Shop has incredible, rotating offerings ranging from cranberry orange loaf and scones to cinnamon buns and black forest tarts. There are also savory breakfast and lunch options, and plenty of armchairs so you can flip through some of the shop’s for-sale books by the fireplace. If you spotted your pals for pastries, they can pay you back from their mobile device via Zelle®, so you can get reimbursed swiftly.

Okay, so this one is in adjacent Ulster County, but we can’t help but mandate all city-escapees find their sliver of West Village wonder upstate at Love, Velma. The private social club for fans of live jazz and the performing arts is located in a secret rumpus room in Ellenville, and you can check its calendar for upcoming events or email hello@modhou.se to inquire about your group experiencing this dimly lit, heavily pouring speakeasy when you’re in town.

Unless you're interested in snowshoeing around, there are said to be about two Ubers in all of Sullivan County this winter, so if you’re not driving your own car or renting one, navigating these parts requires some advanced planning. From the New York City area, NYC Limo VIP provides chauffeur service to/from Sullivan County, as does Upstate D Tours. For parties of four or more, you might find it handy to reserve one of Upstate D Tours’ group packages such as one route that takes you to a trio of breweries with the option to make pit stops in the towns of Roscoe and Livingston Manor to amble along the postcard-worthy main drags or a farm brewery and orchard jaunt to Arrowood Farms, Westwind Orchard, and Stone Ridge Orchard.