The Berkshires Blog

Snowshoeing and Winter Hiking in the Berkshires

While some choose to slide down mountainsides on downhill skis and snowboards or skate through open meadows on cross-country skis, visitors will find many opportunities to get outside and enjoy winter in the Berkshires of Western Massachusetts. Whether Old Man Winter graces us with plentiful snow or it ends up being a leaner snow year, the hundreds of miles of hiking trails throughout the Berkshire Mountains provide seemingly endless routes for winter hiking and snowshoeing. For experienced hikers, winter hiking and snowshoeing only require a little extra gear and knowledge, and those new to winter exploration will find plenty of gentle terrains to get the experience they need for longer hikes. Whatever your experience, get out there and discover what winter in these hills and mountains has to offer.

Do I Need Snowshoes?

Snowshoes are often a necessity from January through early March, especially in the higher terrain. Once the snowpack exceeds a foot, snowshoes will make for easier travel and reduce damage to the trail underneath. If you’re unsure of how deep the snowpack is, call one of the local outfitters in the Berkshires for tips. Arcadian Shop in Lenox and Berkshire Outfitters in Adams both offer snowshoe rentals if you find the snowpack is too deep. Whether you use snowshoes or decide to hike with only your boots, it is a good idea to pack some form of crampon or ice cleats as you will most likely encounter an icy spot or two along the trail.

Winter Hikes and Snowshoeing for Beginners

For some of the Berkshires’ best scenery, changing forest types and gently rolling terrain, explore Beartown State Forest in Monterey. Enter the Main Entrance from Blue Hill Road, via Rte. 23 and park in the lot near Lake Benedict (Benedict Pond). Take the mixed-use trail out of the northwest side of the parking area (be sure to stick to the appropriate trails marked for snowshoeing and hiking as snowshoes can ruin cross-country ski trails). The mixed-use trail travels north for a mile before turning east for another mile where it connects to a snowshoe-only trail which returns back south (follow signs for Benedict Pond) along the lake and to the lot. The loop is about 3.5 miles and should take beginners about 3 hours to complete with rests along the way.

Advanced Winter Hikes and Snowshoeing in the Berkshires

For challenging snowshoeing and winter hikes, there are few mountains in the northeast with as much diversity and access as Mt. Greylock. With 60 – 90 mile views off from the top, the summit is an obvious destination for hikers and snowshoers,  but with over 70 miles of hiking trails, most of which are accessible in winter, Mt. Greylock State Reservation offers enough terrain to keep snowshoers and hikers entertained for many winters. For an alternative to the summit, try the Haley Farm Trail to the Stony Ledge lookout. The trail climbs 2.5 miles from the Hopper Road trailhead in Williamstown to the sweeping views of Stony Ledge. The climb is steep and challenging but rewarding. From Stony Ledge you can continue to the summit for a longer like or retrace your steps back to your car.

Winter is a special time of year in the Berkshires. Get out there and explore all that the snowy forests have to offer, whether hiking on foot or with snowshoes.