Skiing: A Guide to Our Favorite Spots in Western Massachusetts & Southern Vermont

"When snow falls, nature listens." - Antoinette Van Kleef


There is a wealth of opportunity to enjoy our local landscapes here in Western Massachusetts.

Don't hesitate to reach out to inquire about guided skiing experiences with us at Adventure East, cross-country, or otherwise. We hope this selection inspires you to get out on skis this winter - crossing our fingers for snow!


Cross-country -

Cross-country skiing is one of the best ways to experience the unique beauty and serenity of winter in Western Mass. With a treasure trove of nearby gems, you have your pick of options for an invigorating day of cross-country skiing.

Canterbury Farm:

Home to 22 kilometers of groomed trails, with additional backcountry trails only tracked by skiers, this Berkshire farm is a go-to spot for consistent snow coverage and a wide range of trail difficulties. Canterbury is home to an excellent team of certified coaches who can equip and teach lessons to new skiers.

Maple Corner Farm:

Located in Granville, MA at the foothills of the Berkshires, Maple Corner grooms 20 kilometers of trails, and boasts an additional 10 kilometers of backcountry trails as well. The ski lodge is a family friendly environment with fires to warm up and a full snack bar to refuel after a day of skiing.

Northfield Mountain:

Northfield Mountain Cross-Country Ski Area is home to 25 miles of trails, full fleets of rental skis and snowshoes, warming huts, and yurts along the trail. A fully developed cross country ski resort, Northfield has experienced coaches and many unique trails and amenities.

Notchview Reservation:

At elevations consistently above 2,000 feet in Windsor MA, Notchview is a year-round landscape open to cross country skiing, snowshoeing, and hiking in the warmer months. A property owned and managed by The Trustees, Notchview is open from sunrise to sunset. And the 27 total kilometers of groomed trails have some of the best views the Berkshires have to offer. And don't miss out on the skijoring! Notchview Reservation offers skiing with dogs, a unique product to this region.

Stump Sprouts:

A small, family-owned operation for 30 years in Hawley, MA: this is Stump Sprouts. With over 25 kilometers of skiing and snowshoeing and stunning views of the Berkshires and Southern New England, this 450-acre skiing area is a quiet gem. Enjoy a home-cooked meal, stay for a weekend in their rustic lodge, or ski up to their highest point at over 2,000 feet; Stump Sprouts has it all!


Alpine -

You don't have to drive 4 hours north to find fun and challenging alpine skiing areas - we have some excellent, locally owned and operated alpine skiing areas right here in Massachusetts, as well as in nearby New York and southern VT.

Berkshire East:

Nestled in the Berkshires in Charlemont, MA, Berkshire East is a family friendly resort packed with great food, activities, and an excellent ski school. Home to tubing, ziplining and an array of alpine skiing terrain, there is something for everyone.

Mount Snow:

Only 75 minutes away, resting in the southern Green Mountains of Vermont, Mount Snow is a powerhouse of excellent terrain, reliable snowpack and an awarding-winning terrain park, Carinthia. Home to a wide range of lodging and food, stay at Mount Snow for a weekend or drive up for a day. Mount Snow recently joined the Epic Pass.

Jiminy Peak:

Jiminy Peak is leading the way in addressing the climate crisis and moving towards renewable energy, as the mountain relies entirely on wind and solar. Jiminy has some of the best skiing terrain in Massachusetts and is home to an award-winning ski school and adaptive ski school.


Located in Great Barrington, MA, Butternut has some of the best value skiing for midweek passes, coming in at $35 for a single day pass. Another excellent option for southwestern Massachusetts, Butternut has lodging for a weekend stay, tubing, and a top-tier rental shop for all of your gear needs.

Catamount Mountain Resort:

Recently partnered with Berkshire East, Catamount Mountain Resort offers whitewater rafting, hiking, ziplining and excellent introductory skiing terrain on the border of New York and Massachusetts. This resort also boasts an impressive 15 trails of fully illuminated night skiing!

Here are some smaller mountains with a wide range of skiing terrain:

Greylock Ski Club is a small tow rope area in Williamstown, MA. Rarely crowded and operated by a team of locals, this spot is great for new skiers looking for a welcoming community.

Wachusett Mountain hosts ski clinics for all ages, and is an excellent, inexpensive option for alpine skiing in central Massachusetts. Wachusett also has an extensive ski demo fleet if you're interested in testing out some new gear.

Bousquet Mountain, located in Pittsfield, MA, is a small and convenient mountain for those in the Pittsfield area. This spot also allows for inexpensive uphill travel if you're craving some skinning.


Backcountry -

We don't see prominent peaks or vast mountain ranges in the valleys of Massachusetts, but there is still plenty of backcountry skiing to enjoy if you know where to find it. Here are some of the areas we've come to love over the years.

The Massachusetts chapter of the Civilian Conservation Corps has cut trails that are perfect for backcountry exploration. The Thunderbolt Trail on Mount Greylock, for example, is a staple of backcountry skiing in Western Massachusetts. You can check out maps, descriptions, and historical records of the trails that are closest to you here. The Hoosac Range is home to stunning views and variable terrain at Crum Hill, Spruce Mountain, and Mount Greylock.

Dutch Hill and Mount Ascutney are both short drives over the border into Vermont. Dutch Hill, in Searsburg, VT, is home to landscapes cut for all types of ski touring, whether it be telemark, cross-country, or backcountry skiing. Stop by Dutch Hill in the fall to help the Dutch Hill Alliance with brush clearing before the first snow or drive up mid-winter and experience some of the most beautiful scenery in southern Vermont, and some wonderful snow too!

Mount Ascutney is an old ski area in Windsor, Vermont that no longer operates chairlifts. The skiing accessible via the old slopes or the Ascutney State Park access road is second to none when the snow accumulates! Explore the glades of the old resort or cut into the vast ridges of this impressive mountain. Ascutney is home to some of the most challenging and exciting skiing in the region.

Other spots to skin include Mount Toby in Sunderland, MA, Mount Tom, a ski resort that was shut down in the late 1990's in Easthampton, MA, and Berkshire East, which allows skinning for $15/day or $50 for a season. These are excellent options if you're craving some exercise and some quick turns after work.

We hope that this list excites you as winter approaches! As we like to say, the adventures don't stop when the snow starts, in fact, in this case, the winter fun is just about to begin! If you'd like to talk to us about arranging a guided trip for you or for you and a group, please don't hesitate to contact us. We're happy to help you plan a fun and safe ski session.

We hope to see you on the snowy trails and slopes soon!

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