Small-Town Weekends
A Berkshires Holiday Weekend Built Around Two Light Walks
Winterlights in Stockbridge, NightWood in Lenox and 75 trees in Pittsfield, inside ten miles of each other. A two-night weekend that does not require a third day.
Three of the best seasonal installations in western Massachusetts sit within ten miles of each other, and all three run on the same five-week window. A Berkshires holiday weekend built around them fits comfortably into two nights without feeling compressed, which is unusual for a region where most things are forty minutes apart.
Friday night: NightWood at The Mount
Edith Wharton's Lenox estate runs an immersive sound and light walk along a three-quarter-mile route through the woods and gardens, after dark, through late fall and the holiday season. It is the more atmospheric of the two light walks and the less crowded.
The route is unpaved and unlit outside the installation itself, which is a detail people discover at the wrong moment. Real shoes, and a layer more than you think.
Dinner in Lenox after. The village keeps a workable winter core open, which is more than most of the county manages.
Saturday afternoon: Festival of Trees
Hancock Shaker Village in Pittsfield fills with more than 75 decorated trees from November 21 through December 28, Friday through Sunday. Timed tickets on December weekends.
The trees are the draw and the Round Stone Barn in the snow is the reason to go: an 1826 circular barn on a working Shaker site, which is a better building in winter than in summer and almost nobody says so.
If the timing lands on a first Friday, First Fridays at Five runs the Artswalk along North Street in downtown Pittsfield from 5 to 8 PM, free.
Saturday night: Winterlights at Naumkeag
The Trustees put hundreds of thousands of LEDs across the Choate estate gardens in Stockbridge, with music and seasonal food along the route, from late November through the first days of January. Dark December 24 and 25.
Timed entry and it sells out, particularly the weekends before Christmas. Book as soon as the calendar posts in the fall rather than the week of.
Sunday: the museum, if you have the energy
MASS MoCA in North Adams is forty minutes north and worth the drive on a Sunday morning, particularly after December 17 when **Jason Moran's *Black Stars: Writing in the Dark* opens in Building 6. The Chalet**, the winter courtyard bar, is open on weekends. Adults 21+ for the bar.
Where to stay
Lenox and Great Barrington both work as a base and both are inside twenty minutes of everything above. Winter rates run a fraction of the Tanglewood season, and the inns that stay open through the cold months are the ones with real winter regulars.
Book the restaurants before you book anything else. A meaningful share of the county's dining room closes for part of the winter or runs a three-day week, and the list changes year to year.
Compliance, quickly
- 21+ only at every dispensary and for every purchase
- Verify licensed status via the Massachusetts Cannabis Control Commission at masscannabiscontrol.com
- Massachusetts state law prohibits cannabis consumption in public spaces, which covers the Naumkeag grounds, The Mount's woodland route and the Shaker Village site
- Start low, go slow with edibles; both light walks are an hour outdoors in the dark in December
- Never drive after consuming, and the drive between Lenox, Stockbridge and Pittsfield in winter demands it
Current dates for all three installations are on the events hub.