Winter in the Sullivan Catskills: The Cozy Roundup
Plan a cozy winter getaway in the Sullivan Catskills with this roundup of the season’s best things to do, from snowy hikes and small-town shopping to warm drinks by the fire and local eats worth the drive. Whether you are planning a romantic weekend or a friends’ escape, you will find cold-weather adventures and indoor favorites that make the region shine. For a stay that feels charming and tucked away, book a Red Cottage home that is well placed for exploring during the day and unwinding at night.
Downhill Skiing and Snow Tubing
📍 Holiday Mountain
A classic Sullivan County spot for downhill skiing, snowboarding, and winter tubing that makes it easy to turn a cold day into a full-on snow day. Come for the runs, stay for the family-friendly vibe, and warm up after with a quick bite before heading back out.
📍 Villa Roma’s Ski Hill & Chalet
A cozy, resort-style ski hill where you can do winter the easy way with skiing and snow play all in one place. It is a great pick if you want a low-stress day on the slopes followed by comfort-forward downtime.
📍 Bearpen Mountain Sports
A winter adventure hub for tubing, cross-country skiing, and snowshoeing with a fun, outdoorsy Catskills feel. Perfect for groups who want options, fresh air, and a full day of snow activities without overthinking the plan.
Cross-country Skiing, Snowshoeing, + Easy Winter Walks
📍 Sullivan O&W Rail Trail
A scenic, mostly gentle trail that is ideal for an easy winter walk, a snowy bike-style stroll, or a peaceful cross-country ski when conditions line up. It is a great way to soak up the Sullivan Catskills landscape without committing to a steep hike.
📍 East Mongaup River Park
A quiet, nature-first spot for winter hiking, snowshoeing, and cold-weather wandering along the Mongaup. If you want a calm trail moment with woods-and-river scenery, this is an easy add to your winter itinerary.
📍 Mongaup Pond Area
A go-to winter woods vibe with peaceful trails and that classic frozen-lake feel when the temps drop. It is especially dreamy after fresh snowfall and perfect for a slow, scenic snowshoe or walk.
📍 NYSDEC lands in the area
A choose-your-own-adventure option for winter exploring, since many DEC trails are open for snowshoeing and cross-country skiing. Ideal for travelers who want uncrowded nature, flexible trail picks, and a true Catskills winter reset.
Après-ski
📍 Upward Brewing Company
A Livingston Manor favorite for après-ski energy, with craft beer, comfort-forward bites, and a warm, laid-back atmosphere. It is the kind of place you will want to linger, especially after a cold hike or a day on the slopes.
📍 Callicoon Brewing Company
A relaxed riverside-style brewery stop that pairs well with winter weekends and small-town exploring. Swing by for a seasonal pour and an easy meal that feels cozy without trying too hard.
📍 Catskill Brewery
A lively local brewery hangout that is great for post-adventure drinks and casual food in a Catskills setting. Perfect when you want a low-key, group-friendly spot to toast the day and warm up.
📍 Seminary Hill Orchard & Cidery
A Callicoon-area destination for elevated cider, orchard charm, and a cozy bite that feels special in winter. It is a beautiful pick for a slower afternoon, a date-night vibe, or a warm drink with countryside views.
Whether you are here for fresh powder, snowy walks, or a cozy crawl of breweries and cider, winter in Sullivan County is the kind of getaway that feels both easy and unforgettable. Pick a couple outdoor adventures, save room for comfort food and après drinks, and build a weekend that is equal parts active and laid back. Then bring it all home to a Red Cottage home, your warm, tucked-away escape to unwind, reset, and do it all again tomorrow.
