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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

A woman practicing mat Pilates with rings in a bright studio, promoting core strength, posture improvement, and joint-friendly exercises.

Mat Pilates With Aly Steigart

Where:
When: February 27 @ 9:30 am
Learn More
A promotional flyer for a Friday Fitness Series with details on dates, location, pricing, and a QR code for registration.

Friday Fitness Series Winter 2025 – 2026

Where: Cornell Cooperative Extension
When: February 27 @ 10:00 am
Learn More
A promotional flyer for salsa classes, detailing the instructor, venue, schedule, and pricing information.

Salsa Classes

Where: Western
When: February 27 @ 6:00 pm
Learn More

Rock Band Jam Monthly Music Drop-in for Adults

Where: Bethel Woods Center For The Arts
When: February 27 @ 6:00 pm
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A promotional flyer for Bingo Night, featuring dates, times, and prizes, with playful graphics and a raccoon mascot.

Bingo Night With Jake

Where: The Catskill Brewery
When: February 27 @ 6:00 pm
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Live Music With Shane Rennison

Where: Tango Cafe´
When: February 27 @ 6:00 pm
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Cabaret Roulette

Where: Woodbourne Firehouse
When: February 27 @ 7:00 pm
Learn More
Promotional poster for a live music event featuring The Black Legacy Project on February 27 at 7 PM.

The Black Legacy Project

Where: Hurleyville Art Center
When: February 27 @ 7:00 pm
Learn More

Cabaret Roulette

Where: Woodbourne Firehouse
When: February 27 @ 7:00 pm
Learn More

Travel Stories

The Most Colorful Coffee Shop in the Catskills

Next time you’re in the Sullivan Catskills, ask any local where to find the best…

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5 Scenic Catskills Spots to Pop the Question

The Catskills have always been a place where life is supposed to slow down. Where…

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Honey & Rye: How One Gift Became a Catskills Legacy

The Sullivan Catskills region has always been a place of invention and reinvention, where tinkering…

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Your Perfect Catskills Weekend Getaway: No Experience Necessary

A Catskills weekend isn’t something you plan down to the minute—it’s something you let unfold,…

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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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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

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