5 Winter Hikes for Berkshire Families

By Taylor Staubach - Berkshire Family Hikes January 6, 2021

Winter is a wonderful time of year to hike. Blankets of snow and the crisp, cold air bring a fresh perspective to many of our favorite, familiar places. Views are clearer and unobstructed, bugs are a non-issue, and animal tracks turn us all into snow detectives. Check out some of our favorite Berkshire spots for winter hiking. 

Pile on the layers and get out there already! Be sure to have the cocoa ready for your return...

NOTE: As the state releases new guidelines, please practice social distancing guidelines and know that we try to keep these lists as updated as possible, but some of the trails may be closed or have alternate guidelines. If you see a change, please email me at

1. Field Farm, Williamstown

Located in Williamstown, this Trustees of Reservations property is 4 miles of trails through expansive fields, sculpture gardens, and features 2 historic modernist homes. The day we visited the beavers were very busy preparing for winter. Suggested route: Pond Trail, 0.4 miles (around an active beaver pond). Ice Skating Prohibited.

2. Old Mill Trail, Dalton

A Berkshire Natural Resources Council property, the first 0.7 miles of the Old Mill Trail is accessible. Remnants of a 19th-century textile mill are found along the river’s edge. Keep an eye out for hidden fairy stones! Don’t forget to hide them again before you leave.

3. John Lambert Nature Trail, Pittsfield

Maintained by BCC Environmental and Life Sciences students and faculty, this trail can be found to the rear of Berkshire Community College and it’s truly a hidden gem. Enjoy the 75-year old white pine stands, bird-watching and glorious views of the Taconic Range and the Berkshire Hills. There’s also a geocache there! 

4. Canoe Meadows Wildlife Sanctuary, Pittsfield

One of the 1st hikes we ever did was at Canoe Meadows in Pittsfield. ThisMass Audubon property offers 3 miles of well-marked walking trails. A wonderful place to birdwatch and test out your winter "pishing" skills. Don'tforget the binoculars! Sacred Way Trail: 1 mile, sometimes flooded by beaver activity. 

5. Greylock Glen Meadow, Adams

One of our all-time favorite places to get outdoors with the kids. We reviewed this trail in May and returned again on January 1st of 2020 to kick off the NewYear. We even made a custom scavenger hunt for our adventure, the kids loved it! Suggested Route: Glen Meadow Loop, 1.57 miles. The Glen has multi-use trails for hikers, naturalists, skiers, snowshoers, mountain bikers, and snowmobiles. Share your favorite Winter spots with us in the comments! 

For 7 more great winter hikes, check out a full list at