The winter woods can be quiet and beautiful before and after the snow. In the valleys we have trails to walk when the snow is light or snowshoe or ski when it gets deeper — town parks, walks along the Hoosic and Housatonic Rivers and trails easy to reach near the roads.
Higher up, with the fir and spruce, the the snow can get deep even when the lower slopes are clear, and in some places you’ll find groomed trails for cross-country skiing, from Notchview’s wide network to family-owned trails through fields and old wood roads. These can be relaxing places to snowshoe too, quiet but cared for and good for occasional company.
Cross Country Skiing
Canterbury Farm — Dave Bacon and his wife, Linda, groom 22 miles of trails at Canterbury Farm in Becket, along brooks and beaver ponds and through old woodland. They will open for skiing, ski skating and snowshoeing this winter, with ice skating on the pond and ways to warm up outdoors, though they are not for lodging.
Hilltop Orchards — The Vittori family grooms trails for walking and Nordic skiing around the apple orchards they have maintained for more than 30 years on their 200-acre property in Richmond. Walking trails range from two miles up the new Perry’s Peak Trail to an easy trip up the picnic tables. They ask visitors to sign in at the farm store.
Prospect Mountain — Just east of Bennington, more than 30 kilometers of groomed trails open for Nordic skiing in woodford, Vt., when snow falls, with snowshoeing and single-track trails. Agile skiers have been known to come for the 400-foot climb up the mountain.
204 Prospect Access, Woodford, Vt.
Trustees of Reservations — High on the ridge at Notchview, 17 kilometers of trails are groomed and track-set for classical cross-country skiing, eight for skate skiing, and a separate trail system for skijoring, or skiing with dogs, on Route 9 in Windsor. Trustees properties up and down the county offer walking trails and snowshoeing, and ungroomed skiing for the adventurous, from Bartholomew’s Cobble in Sheffield to Mountain Meadow Preserve and Field Farm in Williamstown.
Hiking and Snowshoe trails
Ashuwillticook Rail Trail — Ambling along the Hoosic River and Cheshire Lake, the trail runs for more than 12 miles along the old railroad tracks through Cheshire, Lanesborough and Adams, making it flat, paved and easy to reach. The Southern section is open, and the Northern section is being resurfaced and should re-open in late fall.
Berkshire Natural Resources Council — The BNRC maintains trails across the county, in all sizes, flat or steep, long or short. You can find them on the BRNC’s countywide trail map through their app.
Hopkins Forest — The 2600-acre forest managed by Williams College covers miles of trails and wood roads, many of them gentle and fairly level. A four-mile figure eight loop draws classical skiers in winter, especially on sunny days after fresh powder, p Northwest Hill Road in Williamstown
Kennedy Park — The hardwood forest runs from downtown Lenox toward Pleasant Valley Sanctuary, with carriage roads and 15 miles of trails. Trailheads include an entrance at the north end of Main Street as it heads out of town past the Church on the Hill, one near the Arcadian Shop on Route 7, and one that comes out by Chocolate Springs for thick, rich hot chocolate.
Mass Audubon — Pleasant Valley Sanctuary’s trails are open to visitors, from the flat and comfortable pond loop to the climb up Lenox Mountain, though the visitors center and amenities remain closed for now. Canoe Meadows in Pittsfield and the community gardens are also open, Tracy Brook in Richmond and Lime Kiln Farm in Sheffield.
Springside Park — Easy trails loop through woods and meadow land on 231 acres just off Route 7, north of downtown Pittsfield, surrounding the Hebert Arboretum on North Street in Pittsfield.
Williamstown Rural Lands Foundation — In and around a historic dairy farm, along Route 7 heading north out of Williamstown, WRLF keeps trails through the hayfields and up toward Hopkins Forest and the Taconic Crest Trail. You can start from the old farm at the foot of the hill or from trail heads above the fields, along Bee Hill Road, with a broad view over the valley. Some hillside trails may be steep and slippery in the snow.
Some of these listings first ran in the Holiday 2020 Berkshire magazine, as I gathered them for Anastasia Stanmeyer, and they run here with her go-ahead. Thanks, Anastasia.