“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… 

Field Farm, Williamstown

FREE / 316

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

Read about our Field Farm adventure HERE

Old Mill Trail, Dalton

FREE / 127 Acres

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.

Suggested route – 3 miles out & back. Be sure to cross Route 8 for the most incredible views alongside the Housatonic River. 

Read about our Old Mill Trail adventure HERE


Thomas & Palmer Brook, Great Barrington

 FREE / 219 Acres

Another BNRC property overlooking expansive pasture and woodlands. Climb glacial erratics and contemplate the lives of the Stockbridge-Munsee Mohican Nation that called these lands home. 

 Suggested Route – 0.5 mile accessible loop trail, continue on the wood road to extend your hike. 

Read about our Thomas & Palmer adventure HERE

Canoe Meadows Wildlife Sanctuary, Lenox

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.

Read about our Canoe Meadows adventure HERE.

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 here!

Suggested route – 0.5 mile loop trail

Road's End Wildlife Sanctuary, Worthington

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. 

Read about our Roads End adventure HERE.

Wahconah Falls State Park, Dalton


Located off of Route 9 before the Windsor town line, you’ll find a 40-foot waterfall at the end of a short walk. Wahconah Falls can be a magical place when frozen over  but be cautious of your footing as rocks can be slippery or hidden beneath the snow.

Suggested Route – A 0.5 mile trail follows the upper falls to the town reservoir, returns to the parking lot via the dirt road or retrace your steps. 

Read about our Wahconah Falls adventure HERE.


Greylock Glen Meadow, Adams

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.

Read about our Greylock Glen adventure HERE.

Dorothy Frances Rice Wildlife Sanctuary, Peru

FREE / 300 Acres

Woodlands, meadows and a pond are featured on six different colored trails. There is a well-detailed map at the cabin area to assist in navigating the trails, each of which is a half-mile to one-mile long. Check out the trail log for photos of wildlife that roam the area. 

 Suggested Route – Take the 0.5 mile Yellow Trail off of the wood road where you park, it will take you to the caretaker cabin and the map/intersection of all trails.

Read about our DFR adventure HERE.

Hopkins Memorial Forest, Williamstown

FREE / 2,600 Acres

If you enjoy walking through the woods on winding trails, then Hopkins is a great spot. The trails are wide and well-maintained and there are several options, from a short to longer loops. The HMF contains about 15 miles of trails open to the public for walking, skiing and snowshoeing. 

Suggested RouteThe Nature Trail 0.75 miles, or the Lower Loop Trail 1.5 miles

Bullard Woods, Stockbridge

FREE / 52 Acres

 Visit a rare stand of old-growth forest along the shores of the Stockbridge Bowl. The woods were originally part of the estate surrounding the Highwood manor house, now part of Tanglewood. Hiking trails lead to the shoreline, and a brief walk through the woods, connects to trails at Gould Meadows.

Suggested Route – 1.25 miles of easy walking trails

Read about our Bullard Woods adventure HERE.

Eugene D. Moran Wildlife Management Area, Windsor

FREE / 1,462 Acres

 Located just north of Windsor town center, sits this hilly nature & wildlife conservation area, a great place to visit in the winter. A former dairy farm, it is home to 99 breeding bird species and other wildlife species, and offers views of Mount Greylock. Visitors can see diverse habitats including emergent freshwater marshes, spruce stands, and shrub habitats.

 Suggested Route – 1.4 miles of public trails