Cross-country skiing in the Berkshires centers on Notchview, the Trustees of Reservations property in Windsor with a groomed trail network, a rental shop and lessons, and spreads out to snowshoe routes in Lenox and on Mount Greylock. The 2026–27 season prices are already posted, and Presidents' Day weekend, February 13 to 15, 2027, lands in the middle of the season. For adults 21+ planning a winter weekend on skinny skis or snowshoes, here is where to go, what it costs, and the rules that apply on every trail.
Notchview, Windsor
Notchview sits on Old Route 9 in Windsor, in the hills east of Pittsfield, and it is the county's Nordic center in the full sense: groomed trails, a ticket window, a rental shop and lessons.
- Trails: more than 25 miles in all, with roughly half groomed for classic skiing and 5 miles groomed for skate skiing. Snowshoers can travel alongside the ski trails or head into the backcountry.
- Hours: skiing and snowshoeing daily from 8 AM to 4 PM through March 15, weather permitting. The Budd Visitor Center, with the ticket window and rental shop, is open 8:30 AM to 4:30 PM.
- Day passes, 2026–27: $22 for adults, $16 for seniors 65 and over, $11 for youth 6 to 17, with discounts for Trustees members.
- Season pass: Trustees members can buy an adult season pass for $74 through November 15, 2026, with youth passes free alongside an adult pass. The price rises after that date.
- Rentals: classic ski packages at $23 for adults and $16 for youth, snowshoes at $15 and $10. Rentals are first come, first served from 8:30 AM.
- Lessons: group lessons for ages 12 and up on weekend mornings and Sunday afternoons, subject to weather and enrollment.
Snow in the hill towns and snow in the valleys are two different forecasts, and the Trustees post a Notchview snow report with current conditions. Check it before driving up.
Pleasant Valley Wildlife Sanctuary, Lenox
Mass Audubon's sanctuary in Lenox is the easy snowshoe day. Snowshoes and microspikes are rented in winter on a first-come basis, at $5 an hour or $15 a day for members and $10 an hour or $20 a day for nonmembers, with a one-hour minimum, and they can be taken on any sanctuary trail when conditions allow. Equipment is due back by 3 PM, so it suits a morning on snowshoes. The Lenox page covers the town below.
Kennedy Park, Lenox
Kennedy Park is the town of Lenox's own trail network, on the hilltop north of the village center where the Aspinwall Hotel stood from 1902 until it burned in 1931. Only the stone pillars at the old driveway remain. In winter the trails are open to cross-country skiers and snowshoers, with access from Main Street beside the Church on the Hill. There is no grooming schedule to rely on and no ticket window, so conditions depend on the week's snow.
Mount Greylock, Lanesborough and Adams
The state reservation around the highest point in Massachusetts turns into a snowshoe destination once the summit roads close; the auto roads were open for the 2026 season from May 16 through October 30. With the roads shut, the visitor center on Rockwell Road in Lanesborough becomes the trailhead, and the routes to the summit become long, cold days that call for winter experience and full winter gear. Check the Department of Conservation and Recreation's page for visitor center hours and any winter programs before going. The Adams page covers the east side of the mountain.
A Presidents' Day weekend
Presidents' Day falls on Monday, February 15, 2027, which turns the weekend of February 13 into the long one. A three-day version: Saturday at Notchview while the grooming is fresh, Sunday on snowshoes at Pleasant Valley or Kennedy Park in Lenox, and Monday for the museums before the drive home. Lodging in Lenox and Pittsfield can fill for the holiday, so book early, and read the cancellation terms for a snowless forecast.
For the licensed stores along the way, Pittsfield has seven on the Cannabis Control Commission's Where to Buy map, and Lee and Lenox have three between them. The dispensary directory carries current hours, and the Pittsfield page covers the city between the trailheads.
The rule, plainly
The Cannabis Control Commission, at masscannabiscontrol.com, publishes the state rules:
- Massachusetts state law prohibits cannabis consumption in public spaces. The CCC spells it out as no smoking, vaping or eating cannabis in public places or on federal land.
- An open container of cannabis in a car's passenger area is illegal. Keep purchases closed, in the trunk or a locked glove compartment.
- Driving under the influence of cannabis is illegal.
- Crossing a state line with cannabis is illegal, including the short drive back to New York.
What it means on the trail
Mount Greylock is state land, Kennedy Park is town land, and Notchview and Pleasant Valley are nonprofit conservation properties open to the public under posted rules. All of it is outdoors, shared and off-limits for cannabis. Winter adds its own reasons for a clear head: short daylight, cold that builds fast, icy parking lots and dark drives back over the hills. Adults 21+ buying on the way can verify a store through the CCC's Where to Buy map; purchases ride sealed in the trunk, and edibles follow the start low, go slow rule on the label.
The short version
Notchview in Windsor is the Berkshires' cross-country ski center, with more than 25 miles of trail, $22 adult day passes and rentals for 2026–27, open daily 8 AM to 4 PM through March 15. Pleasant Valley in Lenox rents snowshoes, Kennedy Park has free town trails, and Mount Greylock becomes a snowshoe climb once its roads close. Presidents' Day weekend is February 13 to 15, 2027. Keep cannabis sealed in the car and off every trail. More on the winter calendar is on the events hub.
FAQ
Where can I go cross-country skiing in the Berkshires?
Notchview in Windsor is the main groomed Nordic center, with more than 25 miles of trail. Kennedy Park in Lenox has town trails open to skiers and snowshoers.
How much is a Notchview day pass?
For 2026–27, $22 for adults, $16 for seniors 65 and over, and $11 for youth 6 to 17, with member discounts.
Can I rent snowshoes in the Berkshires?
Yes. Notchview rents snowshoes at $15 for adults, and Mass Audubon's Pleasant Valley Wildlife Sanctuary in Lenox rents snowshoes and microspikes by the hour or day.
When is Presidents' Day weekend 2027?
Presidents' Day is Monday, February 15, 2027, so the long weekend runs February 13 to 15.
Can you use cannabis on Berkshires ski trails?
No. Massachusetts state law prohibits cannabis consumption in public spaces, and the trails at Notchview, Kennedy Park, Pleasant Valley and Mount Greylock are all public or open to the public.
