10 NEW Trails: Holiday Mountain Enters Its Biggest Season Yet
A Southern Catskills favorite is dramatically expanding its terrain this winter with 10 new trails and a new chairlift
MONTICELLO, NY – September 2026 – If you haven’t been to Holiday Mountain before or haven’t been out in a few years, this winter is the time to come back.
Holiday Mountain is heading into the 2026–2027 season with its biggest terrain expansion in decades, adding 10 new trails this season. This will take the mountain from just two operating trails when the Taylor family took over in 2023 to up to 21 trails this winter.
The centerpiece of the expansion is a new chairlift serving 10 new trails along NY 17, opening up a completely different section of the mountain with terrain designed for a range of abilities. From beginner-friendly runs to more challenging terrain, the expansion gives skiers and snowboarders significantly more room to explore.
“We’re super excited about our upgrades and working full speed to make it all a reality by winter,” said Mike Taylor, Owner. “This is definitely the wildest change in our 70 years.”
Along with the new trails, the mountain this year will have a new chairlift, along with chair replacements on the third chairlift, and the newer quad chairlift that was only just installed two seasons ago, creating better access to the expanded terrain.
To support the additional trails, Holiday has also installed a brand-new snowmaking system covering 100% of the mountain. The new system is designed to provide more consistent snow coverage and help Holiday open and maintain its expanded trail network throughout the season.
“We’re a family-focused mountain, but that doesn’t mean we’re only for beginners,” said Drew Taylor, Director of Market Development. “Our terrain ranges from beginner trails all the way to double black diamonds, and with this season’s expansion, we’re able to offer one of the most diverse mixes of terrain in the area.”
For longtime Holiday Mountain guests, the expansion also brings back the opportunity to explore terrain that hasn’t been available in years, while introducing an entirely new section of the mountain for a new generation of skiers and riders. Holiday Mountain is also expanding its role in high school and collegiate ski racing, weekend youth programs, and after-school ski and snowboard clubs for local communities and schools.
Holiday Mountain is also fully lit for night skiing, with 100% of its terrain illuminated, allowing guests to take advantage of the expanded trail network well after the sun goes down.
Located just off NY 17, approximately 20 minutes from Middletown and just under 2 hours from NYC, Holiday Mountain remains an easy day-trip destination for the Hudson Valley, NYC, and surrounding areas.
This winter, Holiday Mountain is bigger, more accessible and ready for more skiing and riding than ever before.
Holiday Mountain – Great Skiing Closer.