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Winter Sports & Snow Play | Ski, Skate & Snowshoe

Frosted trails mark the boundary between getting here and truly being here. Step out your door and into the winter wonderland of the Sullivan Catskills during the snowiest season. Sleigh rides and starry skies, snowfall hush and laughter’s rush, mittens on and worries off.

Featured Businesses

A snowy landscape featuring ski lifts, trees, and people on a chairlift, creating a picturesque winter scene.

Holiday Mountain

845-796-3161
99 Holiday Mountain Road
Monticello, NY 12701
A vibrant carnival scene at night featuring a large, illuminated ferris wheel and colorful tents bustling with activity.

Neversink Agricultural Society

Grahamsville Fairgrounds
Grahamsville, NY 12740
A cozy hotel room featuring two beds, warm wooden accents, and a view through large sliding glass doors, complemented by green walls and a patterned rug.

Roscoe Mountain Club

607-498-5000
100 Fairway View Dr.
Roscoe, NY 12776
A scenic pathway adorned with colorful autumn leaves, bordered by trees in vibrant fall colors under a cloudy sky.

Sullivan O&W Rail Trail Alliance

PO Box 74
Hurleyville, NY 12747

Upcoming Events

Menu for a Chinese New Year sample platter including various appetizers and desserts, with pricing and restaurant details.

Chinese New Year

Where: Bixbys Derby
When: February 17 @ 5:00 pm
Learn More
Promotional flyer for a Fly Tying Night at Upward Brewing, with details on time, location, and an invitation for newcomers.

Get Down With Fly Tying

Where: Upward Brewing
When: February 17 @ 5:30 pm
Learn More
A promotional poster for the 2026 Callicoon International Gay Film Series, showcasing a schedule of films and ticket information.

Edge of Seventeen

Where: Callicoon Theater
When: February 17 @ 7:30 pm
Learn More
Promotional flyer for Pasta Night at a restaurant, highlighting various pasta dishes, time, and pricing details.

Pasta Night!

Where: Roscoe Mountain Club
When: February 18 @ 4:00 pm
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A flyer for the 2026 Caregiver Resource Center, detailing monthly virtual support groups for caregivers, including dates and registration information.

Caregiver Resource Center

Where:
When: February 18 @ 6:00 pm
Learn More
A close-up of ice skates gliding on an ice rink, advertising disco nights in February with bright, colorful lighting.

Disco Nights At The Ice Rink

Where: Roscoe Mountain Club
When: February 19 @ 8:00 am
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Promotional flyer for a Thursday girls' dinner at Brew Lock Hill, featuring a small Caesar salad, Parmesan truffle fries, and a choice of martini.

Girl Dinner

Where:
When: February 19 @ 11:30 am
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Promotional poster for "Thirsty Thursdays" event at The 1907, featuring discounts on drinks and appetizers from 4 to 9 PM.

Thirsty Thursday

Where: Roscoe Mountain Club
When: February 19 @ 4:00 pm
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A promotional flyer for weekly community movie screenings supporting local organizations, encouraging attendance to assist families affected by SNAP benefit reductions.

Reel Good Thursdays

Where: Hurleyville Art Center
When: February 19 @ 6:00 pm
Learn More
Aerial yoga studio with colorful hammocks, displaying class schedules and times for Thursdays, Saturdays, and Sundays.

Aerial Yoga

Where: Mountaindale Yoga
When: February 19 @ 6:00 pm
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Travel Stories

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Little Barn, Big Stage for Live Theater in the Catskills

From a pinball-like journey through acting, law and back again, Franklin Trapp’s winding path led…

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Chasing the Catskills’ Wild Side of Winter

Winter in the Catskills offers raw beauty and honest adventure, from family-run slopes to frozen…

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The Only Catskills Bucket List You Need in 2026

A just-90-miles-from-NYC bucket list of the essential Sullivan Catskills experiences to have in 2026…

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Plan Your Trip

Unexpected wonder and wonderful encounters start here.

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A serene lake view with a small boat resting on the shore, surrounded by lush greenery and a bright blue sky.

Winter sports in cold-weather fun

When the first snowflakes fall, the Catskills shift gears from river rhythms to alpine adventure. The same forests that hum with summer cicadas become playgrounds for skiers, snowshoers and anyone chasing a little winter magic.

Holiday Mountain goes big

At Holiday Mountain in Monticello, family-friendly fun meets serious upgrades. With new snowmaking systems, improved night lighting and a re-imagined terrain park, the resort offers everything from beginner slopes to a 350-foot snow tubing run. A revitalized northern lodge and expanded parking make the experience smoother and more festive than ever.

Ski & stay at Villa Roma

In Callicoon, Villa Roma Resort blends cozy accommodations with lift-served skiing, snowboarding and tubing. With 100% snowmaking coverage, rental gear and both private and group lessons, it’s the perfect base for a winter Catskills weekend getaway. Afterward, unwind with a hot drink by the fire or a soak in the indoor spa.

Skating & snowshoeing

When lakes freeze, the county glides into another rhythm. Lace up skates at Callicoon Hills, Roscoe Mountain Club or Upward Brewing Co., where pond skating pairs perfectly with a craft beer beside a bonfire. For snowshoeing or cross-country trails, head to Walnut Mountain Park in Liberty or the O&W Rail Trail for gentle winter hikes. Don’t have gear? Fortress Bikes and Morgan Outdoors have rentals ready to go.

Winter sports & fun in Sullivan County

When the snow falls, the Catskills transform into a playground of alpine adventure and small-town charm. From ski slopes to frozen ponds, winter here is more than a season. It’s a celebration.

  • Downhill skiing and snowboarding (Holiday Mountain, Villa Roma Resort): Family-friendly slopes with modern snowmaking, night skiing and mountain views.
  • Snow tubing (Holiday Mountain, Villa Roma Resort): Fast, fun and perfect for all ages with easy lifts and well-groomed runs.
  • Ice skating (Callicoon Hills, Roscoe Mountain Club, Upward Brewing Co.): Glide under open skies and warm up by rink-side fires at favorite local gathering spots.
  • Cross-country skiing and snowshoeing (Walnut Mountain Park, O&W Rail Trail): Peaceful trails that wind through forest glades and rolling countryside.
  • Winter hiking (Bashakill WMA, Mongaup Pond Campground): Snow-dusted paths for quiet exploration and wildlife spotting.
  • Snowmobiling (state trails throughout Livingston Manor and Neversink): Miles of groomed backcountry routes for thrill-seekers and scenic riders alike.

Here, winter doesn’t slow things down—it brings the Catskills to life in a whole new way.

PLAY - Outside the Ordinary

Find your fun through music, markets, mountains, and memories.

Wurtsboro Antique Market

845-644-4132
86 Sullivan St.
Wurtsboro, NY 12790

Smith Family Farm II LLC

845-807-2461
4399 State Route 52
Jeffersonville, NY 12748

Walnut Mountain Park

73 Walnut Mountain Road
Liberty, NY 12754

The Monster Golf Club

(833) 586-9358
750 Resorts World Drive
Monticello, NY 12701

Coil + Drift

917-664-4483
106 Dewitts Flats Road
Jeffersonville, NY 12748

Covert Creek Outfitting

845-475-5033
11 Lyman St
Port Jervis, NY 12771

Crooked Willow Pottery

845-701-7978
2016 State Route 17B
Bethel, NY 12720

Crystal Connection

845-888-2547
116 Sullivan St.
Wurtsboro, NY 12790

County Road Bakery

845-887-5137
43 Lower Main Street
Callicoon, NY 12723

D & H Canal Interpretive Center

845-888-5040
16 Bova Rd.
Summitville, NY 12781

Davidson’s General Store

845-439-1190
2 Goff Road, Suite 1
Livingston Manor, NY 12758

Cunningham Family Farms

845-583-4083
233 Hurd Parks Rd.
Swan Lake, NY 12783

Delaware Highlands Conservancy

845-583-1010
571 Perkins Pond Rd
Beach Lake, NY 18405

Delaware Valley Arts Alliance

845-252-7576
37 Main St.
Narrowsburg, NY 12764

Delaware Valley Farm and Garden Center

845-887-5100
30 Viaduct Road
Callicoon, NY 12723

Delaware Valley Opera

845-887-3083
6692 Route 52
Lake Huntington, NY 12752

Dette Flies

845-439-1166
13 Main Street
Livingston Manor, NY 12758

Diehl Homestead Farm

845-796-8867
93 Diehl Rd
Callicoon, NY 12723

Driftwood Ranch

845-583-5555
49 Kilcoin Road
White Lake, NY 12786

Duke Pottery

607-498-5207
855 County Road 93
Roscoe, NY 12776

Make time for what matters.
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