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December 2019

Skiing and riding santas.

10th Annual Skiing & Riding Santa Day

December 15 @ 9:00 am - 4:00 pm
Windham Mountain, 19 Resort Drive
Windham , NY United States

Windham Mountain Resort welcomes all skiing and riding Santas! Kick off the winter holiday season and help us raise money for The Windham Community Food Pantry. 

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Tavern 23 at The Winwood Inn.

Tasty Tunes at Tavern 23

December 20 @ 7:00 pm - 10:00 pm
Tavern 23, 5220 State Route 23
Windham, NY 12496 United States

Visit Tavern 23 Fridays from December 20, 2019 through March 13, 2020 for live music from 7:00pm – 10:00pm.

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Holiday Mash and Bash

December 21 @ 10:00 am - 4:00 pm
Windham Mountain, 19 Resort Drive
Windham , NY United States

Windham Mountain welcomes all level abilities skiers and riders to participate in this years Holiday Mash and Bash event! 10am – 12pm: Registration on the Patio. It’s a $10 donation to the SHRED Foundation to participate in the event. https://shredfoundation.org/ If using the lift, a lift ticket is required, or an Uphill Travel ticket ($20 per day or $60 for Season) is required. 12pm- 4pm:  SHRED

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People enjoying live music in Seasons restaurant.

Seasons Winter Concert Series: The Blitz

December 21 @ 2:00 pm - 5:00 pm
SEASONS, 19 Resort Dr.
Windham, NY 12496 United States

Local favorites, The Blitz, will have you dancing away the après to classic rock covers! They’ll play from 2:00 pm – 5:00 pm.

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People enjoying live music in Seasons restaurant.

Seasons Winter Concert Series: Mark Gamsgager

December 26 @ 8:00 am - 5:00 pm

Americana at its reverb-driven best, with a distinctive sonic stamp courtesy Gamsjager’s Gretsch and his great big voice.  His duo will play for après from 3pm to 6pm.

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Snowboarders riding rails.

Catskill Mountain Series: Rail Jams 1 & 2

December 27 @ 8:00 am - 4:00 pm
Windham Mountain, 19 Resort Drive
Windham , NY United States

The Catskill Mountain Series Regional Pro/Am events are centered on FUN and skill-development in a relaxed competitive environment. A true grassroots competition experience with safe, fun and fair events which allow aspiring competitors of all ages to get together and have some fun.

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People enjoying live music in Seasons restaurant.

Seasons Winter Concert Series: Southbound

December 27 @ 3:00 pm - 6:00 pm

Regional country band, Southbound, plays modern country hits plus some classics from the past few decades from 3pm to 6pm.

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Wine glasses lined up for a tasting.

The Adaptive Sport’s Foundation’s Wine Tasting & Art Auction

December 27 @ 6:00 pm - 10:00 pm
Windham Fine Arts, 5380 Main Street
Windham, NY 12496 United States

A wine tasting and live art auction in support of The Adaptive Sports Foundation.

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Tavern 23 at The Winwood Inn.

Tasty Tunes at Tavern 23

December 27 @ 7:00 pm - 10:00 pm
Tavern 23, 5220 State Route 23
Windham, NY 12496 United States

Visit Tavern 23 Fridays from December 20, 2019 through March 13, 2020 for live music from 7:00pm – 10:00pm.

Find out more »

People enjoying live music in Seasons restaurant.

Seasons Winter Concert Series: Nite Time

December 28 @ 8:00 am - 5:00 pm
SEASONS, 19 Resort Dr.
Windham, NY 12496 United States

New York City’s premier party band come to Windham Mountain for après from 3pm – 6pm.

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