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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

Holiday Mountain

845-796-3161
99 Holiday Mountain Road
Monticello, NY 12701

Neversink Agricultural Society

Grahamsville Fairgrounds
Grahamsville, NY 12740

Roscoe Mountain Club

607-498-5000
100 Fairway View Dr.
Roscoe, NY 12776

Sullivan O&W Rail Trail Alliance

PO Box 74
Hurleyville, NY 12747

Upcoming Events

Barn Party

Where: Van Smokey
When: January 17 @ 5:00 pm
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Karaoke at Rafters Tavern

Where: Rafters Tavern
When: January 17 @ 6:00 pm
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Comedy at Big Eddy Brewing

Where: Big Eddy Brewing & Smokd
When: January 17 @ 7:00 pm
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The Cameramen Live! at Van Smokey

Where: Van Smokey
When: January 17 @ 7:00 pm
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Sunday Morning Knitting Circle

Where: Vintage Passtimes
When: January 18 @ 9:00 am
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Starting Native Seeds Workshop

Where: Mamakating Enviornmental Education Center
When: January 18 @ 1:00 pm
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Soup & Snuggles

Where: Maple Woods Farm
When: January 18 @ 2:00 pm
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All Day Happy Hour

Where: The Eldred Preserve
When: January 18 @ 3:00 pm
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Travel Stories

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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Roscoe Beer Co.: Trout Town’s Other Catch

It’s easy to appreciate a message that gets directly to the point. The sign outside…

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Where the Holidays Feel Homemade

From first snow to first chair, locals share the holiday moments that make the Sullivan…

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Jingle Bells & Holiday Magic in the Catskills

Holidays here are when entire communities get cozy. Jingle bells hang from doors and dog…

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How Holiday Mountain Found Its Way Home

Ask any kid who grew up in the 1970s and early 80s near a small…

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Plan Your Trip

Unexpected wonder and wonderful encounters start here.

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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.

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

Emmanuelle Skincare & Wellness

845-747-2344
7 Main Street
Livingston Manor, NY 12758

DROOZ + Company

315-380-7999
16 Pearl Street
Livingston Manor, NY 12758

Make time for what matters.
Reserve your getaway now.

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