The Berkshires empty out twice a year. Once in April, when the snow turns to mud, and once in November, when the leaves are down, the foliage buses have gone home and the ski areas are still making snow. New Englanders call the November version stick season. It is the most underrated hiking month in the county: long views through bare trees, cold clear air, no parking fights at the trailheads, and inn rates that finally make sense.

It also comes with three changes that catch visitors out. The big mountain closes its roads, the days get short fast, and hunting season starts.

What closes

Mount Greylock's auto roads close for the season on October 30, 2026, and Bascom Lodge on the summit runs a warm-weather season that ends in October. The mountain is still there, but after the 30th the summit is a hike, not a drive. That is a long, serious day in November, with summit weather that can run well behind the valley. For most visitors, the better Greylock plan this month is the lower trail network out of the Greylock Glen Outdoor Center in Adams, which keeps its trails open dawn to dusk.

Seasonal parking lots are the other surprise. Some trailhead lots are not maintained once winter arrives, Monument Mountain's among them, so a first snow can change the plan overnight.

The light

The clocks fall back on Sunday, November 1, and by late November sunset comes before 4:30 PM in the Berkshires. In a valley under a ridge, usable light ends earlier than that. Start every hike by noon, carry a headlamp regardless of the planned distance, and turn around on time rather than on distance.

Hunting season, plainly

Massachusetts shotgun deer season runs November 30 through December 12, 2026, the two weeks after Thanksgiving. Archery season runs through the weeks before it. Hunters are required to wear 500 square inches of blaze orange during shotgun season, and anyone else in the woods should borrow the idea.

What it means for your hike

• Wear blaze orange on every trail that is not a posted no-hunting property: a hat and a vest at minimum. Dogs too.
• Sundays are the easy day. Massachusetts does not allow hunting on Sundays, which makes Sunday the most relaxed day in the woods all season.
• Choose sanctuaries in shotgun week. Mass Audubon prohibits hunting at Pleasant Valley, which makes it the obvious first-week choice.
• Stay on marked trails and keep voices normal. Being heard is part of being seen.

Four stick-season hikes

Monument Mountain, Great Barrington

A Trustees reservation four miles north of Great Barrington on Route 7, open sunrise to sunset with a $10 parking fee for nonmembers. The trails to Peeskawso Peak are short and steady, under an hour up for most hikers, and the ridge views open wide once the leaves are gone. It is also a literary pilgrimage: Herman Melville, Nathaniel Hawthorne and Oliver Wendell Holmes Sr. climbed it together in August 1850, sheltering from a thunderstorm on the way. The lot is not maintained in winter.

Pleasant Valley Wildlife Sanctuary, Lenox

Mass Audubon's sanctuary on West Mountain Road in Lenox spans more than 1,400 acres across Lenox and Richmond, with about seven miles of trails. The All Persons Trail around Pike's Pond is a flat half-hour loop where beavers are a common sighting, and the climbs toward Lenox Mountain give real elevation for anyone who wants it. Trails are open dawn to dusk; admission is $5 for adults and $3 for seniors and children. Dogs are not allowed, and hunting is prohibited, which makes it the safest bet in shotgun week.

Greylock Glen, Adams

The town-run Greylock Glen Outdoor Center opened in October 2024 on the eastern flank of Greylock, a net-zero building with a café, restrooms and exhibits. The Glen Meadow Loop starts at the back door: gravel, gently sloping, and one of the best low-effort views of the mountain in the county. The center itself is open Wednesday through Sunday on seasonal hours. Wear orange here, as on any trail that is not posted no-hunting.

The Ashuwillticook Rail Trail

For a gray day or a short one, the Ashuwillticook is a paved, car-free, ten-foot-wide state park trail on the old Boston & Maine Cheshire Branch, about 14 miles from Pittsfield through Lanesborough and Cheshire to Adams. The Cheshire Reservoir stretch is the scenic middle. No hills, no navigation, no excuses.

A stick-season weekend

• Saturday: Monument Mountain in the morning, lunch in Great Barrington, a slow afternoon in town.
• Sunday: The no-hunting day, so take the longer walk: Greylock Glen and the Meadow Loop, with a stop at the center.
• Monday, if staying: Pleasant Valley, then the drive home before dark.

Cannabis and the trail

The trails above are public spaces, and Massachusetts state law prohibits cannabis consumption in public spaces. That includes state reservations, the rail trail, Trustees and Mass Audubon properties, and every trailhead parking lot.

• Adults 21+ only, with valid photo ID at any licensed retailer
• Verify licensed status via the Massachusetts Cannabis Control Commission at masscannabiscontrol.com
• Purchases stay sealed and in the trunk while driving to trailheads
• Start low, go slow with edibles, and never on a hiking day; impaired judgment on a short-daylight trail is a rescue call waiting to happen
• Never drive after consuming; Berkshire back roads are dark, winding and deer-heavy in November

Licensed stores across the county are listed in the dispensary directory. Holiday weekends and winter events are on the events hub.