The Catskills Winter Season, 2026 Into 2027

The Catskills winter calendar has a structural problem every year: the dates people need to book around are announced after the lodging is gone. Hunter and Belleayre confirm opening day a week or two out, because they are waiting on the weather. The ski weekends that fill Tannersville and Phoenicia post in the fall. Anyone planning a 2026–27 winter here is working from patterns rather than confirmations, and the pattern is reliable enough to book on.

Opening days

Hunter Mountain typically opens the third or fourth Saturday of November on machine-made snow off the summit, which makes it the first Catskills mountain turning lifts most seasons. Tannersville fills the same weekend. Book before the date is confirmed rather than after.

Belleayre, the state-run mountain above Pine Hill, opens on a weather-dependent date in late November or early December, usually a week behind Hunter. Fifty trails, the shortest lift lines of the three Catskills mountains, and the cheapest midweek ticket in the region. Windham runs its own schedule to the north.

Confirm all three on the mountains' own sites before driving up. A projected opening date is a forecast, not a promise.

The weekends that book out

Two queer ski weekends anchor the mid-winter calendar and both fill the surrounding lodging. Hunter's LGBTQ+ Ski & Ride Weekend has run in late January in recent seasons. Catskills Pride Ski Weekend at Belleayre follows at the turn of January into February, built around a Pride Glide down the mountain, an afternoon tea dance at Belleayre Lodge and a night program that has run at the Rosendale Theatre. Ulster County Tourism posts the confirmed dates in the fall. Phoenicia and Pine Hill lodging goes first.

What runs before the snow

October is the region's busiest month and the reason the winter feels quiet by comparison. Peace, Love & Pumpkins at Bethel Woods runs through October on the 1969 festival grounds: thousands of hand-carved jack-o'-lanterns along the garden trails, about an hour at a walking pace, with Harvest Festival Sundays earlier in the month adding wagon rides and a corn maze. The Woodstock Film Festival takes Woodstock village and three other towns October 14 through 18. The Phoenicia Flea puts up its last outdoor edition of the year at Oliver's in Mount Tremper.

December, and the lights

Peace, Love & Lights returns to Bethel Woods from around Black Friday through New Year's Eve: miles of drive-through display, a walk-through option on Mondays, a Holiday Hub with live music and markets, and a drone show on select nights. Gates run 5 PM to 10 PM with last entry at 9. The 2026 dates are announced in the fall, so confirm before booking a room in Callicoon or Livingston Manor around it.

The part nobody plans for

Mid-January through early March is the actual Catskills winter: cold, quiet, cheap, and the best time to be here if skiing is not the point. Rates in Margaretville, Andes and Roscoe drop hard after New Year's. Restaurants run limited winter hours and several close two or three days a week, so call rather than assuming. The fire-tower hikes are open and mostly empty, which requires microspikes and a real assessment of daylight rather than optimism.

Compliance, quickly

• 21+ only at every licensed dispensary and for every purchase
• Verify licensed status via the OCM QR code at cannabis.ny.gov
• New York state law prohibits cannabis consumption on state-owned land and in public spaces, which covers Belleayre, the Catskill Forest Preserve and every trailhead in it
• Start low, go slow with edibles, and account for cold weather slowing everything down
• Never drive after consuming; Route 28 and the mountain approaches are unforgiving in winter

Current dates for all of the above sit on the events hub.