Winter is when our backyard becomes a playground—whether you’re at these area resorts to shred the gnar or just cozy up for the aprés ski.
By Audrey Chamberlin
When winter rolls around, I always get the itch to go play in the snow.
Despite being far removed now from Chicago winters, the first snowfall always reminds me of early mornings waking up, throwing on my boots and coat and rushing out to meet the bus that took a group of us kids Upstate to a ski mountain just across the state line. It was a notable highlight of school breaks and winter free time—and I still think there’s nothing quite like the feeling of zipping down a mountain as fast as your skis will take you. It’s undeniably and unbelievably exhilarating.
Initially, I worried that I wouldn’t be able to find space to ski after I moved here, but I was gladly proven wrong by the vast and excellent options just a day trip away. If you’re also missing the feeling of snow underfoot and wide-open mountains, here are a few places you can go whether you’re a bunny-hill beginner or a seasoned slope veteran.
It’d be hard to talk about Upstate skiing without mentioning Windham Mountain Club in Greene County, so let’s start there. This exclusive club offers 54 different ski trails (tuned for both beginners and experts), six terrain parks between them and nearly a dozen chairlifts that can move more than 20,000 guests an hour. There are several long and winding easy trails, perfect for beginners (or those out of practice), and a clear build up to more difficult courses as the day goes on. Even the six terrain parks are designed to help build skills, with the easiest one featuring small jumps and rails, and the most difficult featuring drop offs, boxes and rails. Off the slopes, the resort offers several different first-rate restaurants, condos for longer trips and a luxury spa for members. In the offseason, the resort features golfing, hiking, fishing and many other outdoor activities for its lucky members.
Up in the Catskills is Hunter Mountain, a popular resort with plenty of trails to beckon guests from all over the area. The paths consist of mostly medium difficulty courses, though there’s a designated section of the park for those just learning to ski or snowboard, as well as lessons for those interested. The mountains feature 13 different lifts, with four terrain parks and 67 distinct trails to follow. The hills also feature snow tubing, with both single- and double-inner tubes available and a magic-carpet-style lift to bring guests back to the top. The resort offers several kinds of lodging, several restaurants including two bars, equipment rentals and even custom gear molding and fitting. This resort has a more laid-back vibe, better for families and beginners.
Over in the Berkshire mountains is Ski Butternut, a cute, two-peak ski slope boasting 22 trails, 10 lifts and snow tubing in Great Barrington, MA. There are a few long, winding tracks that’ll take you from one side of the mountain to the other, as well as more difficult sections like two terrain parks or a course made up of moguls for more experienced skiers to attempt. The lower lodge contains a massive store for ski and snowboard gear of all kinds, as well as some options for food, beer and wine. This resort has a detailed webpage to introduce each of its courses to people new to the slopes, allowing people to see what they may be capable of and how to access each branching trail.

Also in the Berkshires, in Charlemont, MA, Berkshire East Mountain Resort is going to better satisfy those expert skiers in your group. Featuring several double black diamond tracks (the most difficult rating), this cozy resort offers six lifts and both day and nighttime access to its trails, which intersect frequently for an easily adjustable experience. There’s something for everyone here: Berkshire East also offers tubing and a few smaller spaces to practice for beginners. Their green ranked courses (the easiest marking) are long and separated from the harder courses for people who want a more laid-back experience. The lodge offers a full restaurant and bar, with a “mug club” subscription offering free drinks for frequent visitors. Ski and snowboard lessons are also available and a robust equipment rental saves time for those traveling far distances. There’s no overnight lodging, but easy road access means getting home should be a breeze.
Don’t forget the snow tires.












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