“Let us not wish away the winter. It is a season to itself, not simply the way to spring. Winter is a table set with ice and starlight.” – Greta Crosby

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


1. Field Farm FREE / 316 Acres

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 routePond Trail: 0.4 miles (around an active beaver pond) Ice Skating Prohibited


2. Steepletop FREE / 1,230 Acres

 The largest Berkshire Natural Resources Council property, located in both New Marlborough and Sandisfield. A mix of old-growth and young forest, stonewalls and brooks, Steepletop offers 5 miles of maintained trails. This is a great place to go hunt for animal tracks after a fresh dusting of snow.

Suggested route – Louise Lane: (North Loop) 2.2 miles Open For Snowshoeing & Cross Country Skiing


3. Bullitt Reservation FREE / 265 Acres

 Another Trustees property in Ashfield and Conway. This former farm and summer retreat of U.S. ambassador William C. Bullitt, has ample fields, woodlands and streams to explore. Check out the historic farmhouse and the neighboring beaver ponds.

 Suggested RoutePebble Trail: 1mile. Keep an eye out for “The Pebble”a large glacier erratic on the trail.


4. Canoe Meadows Wildlife Sanctuary FREE / 253 Acres

 One of the 1st hikes we ever did was at Canoe Meadows in Pittsfield. This Mass Audubon property offers 3 miles of well-marked walking trails. A wonderful place to birdwatch and test out your winter pishing skills. Don’t forget the binoculars!

 Suggested Route – Sacred Way Trail: 1 mile Sometimes flooded by beaver activity.


5. Housatonic Flats FREE / 26 Acres

Stretching along a half-mile of Housatonic riverbank, this BNRC property in the center of Great Barrington is the perfect spot to get your family a quick dose of the outdoors. Terrific place to bring Fido along too.

 Suggested Route – Housatonic Flats Trail0.9 mile round-trip Leashed dogs please.

6. Road’s End Wildlife Sanctuary FREE / 190 Acres

Another Mass Audubon gem in Worthington, offering two gentle loops through fields and forest, most of it bordering brookside. Keep an eye out for the large “Wolf Trees.”

 Suggested Route – Brookside Trail Loop: 0.5 mile Note: The parking area is not plowed in the winter. Park at the end of Corbett Road and walk to access road to the trailhead. 

7. The Cascades FREE 

Maintained by the Trustees, this short river walk follows the Notch Brook in North Adams.

 The entire hike takes about 1.5 hours and is flat enough for even the most inexperienced to enjoy a taste of nature. Always be cautious of ice in winter and bring along Yaktrax or hiking poles to ensure safety!

 The parking lot is located at the end of Marion Ave, at the Northern Berkshire YMCA. Please be respectful of the YMCA & elementary school especially during school hours.

 Check out this link for a cool video of The Cascades in winter.

8. Greylock Glen Meadow FREE / 1,063 Acres

One of our all-time favorite places to get outdoors with the kids. We reviewed this trail in May and returned again January 1st of 2020 to kick off the New Year. 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!