There are a variety of holiday-themed events this weekend to get yourself into the festive spirit including tree lightings, live music, a brunch, and more. Find a full list of holiday bazaars and fairs here; upcoming holiday events can be found here.

 

Editor's Pick 

 

Stockbridge Main Street at Christmas

Dec. 1 until 3

 

The main street in Stockbridge will be transformed into a Norman Rockwell painting. The town becomes a magical New England village decorated with holiday wreaths and festive lights for the season. More information here. 

 

Friday

 

Pittsfield Annual Tree Lighting 

Park Square, Pittsfield

Time: 6 p.m. 

 

Santa and Mrs. Claus will arrive to ring in the holiday season. The event also features hot chocolate and candy canes. Bring a nonperishable food item for the Christian Center's food pantry. The annual tree lighting is part of Downtown Pittsfield’s Festive Frolic weekend event. 

 

Lenox Annual Tree Lighting 

Lilac Park, Lenox 

Time: 5:45 p.m. 

 

Santa will be visiting Lilac Park for the annual tree lighting. The event will feature performances by Lenox Community Center’s Chorus starting at 5:45 p.m. and Santa will arrive at 6 p.m. to light the tree. Pictures with Santa to follow. 

 

Free Gallery Tours 

Clark Art Institute, Williamstown 

Time: 10:15 a.m. 

 

New parents and caregivers are invited to print their infants into the galleries for a guided tour of the institute's permanent collection. 

 

This special program provides new parents the opportunity to socialize with other community members in a casual environment. 

 

Information here.

 

First Friday

Downtown North Adams

Time: 6 p.m. 

 

Join or listen to New York composer Phil Kline’s walking symphony ‘Unsilent Night as part of 

Community members of all ages are invited to bring their sound amplification devices whether it's their phones, Bluetooth speakers, boomboxes, or other devices. Download the music tracks in advance online or through the Unsilent Night app.

 

A limited number of Kline’s vintage boomboxes and cassette tapes will be available for use on a first-come, first-served basis.

 

Gather at Martin Puryear’s Big Bling Installation at 4 Marshall St. starting at 5:30. At 6 p.m. the walking symphony made up of community members will weave through downtown and end at Hotel Downstreet.

 

More information here. 

 

First Fridays Artswalk

Downtown Pittsfield

Time: 5 to 8 p.m.

 

It's the first Friday of the month, art enthusiasts know what that means — the city's First Friday Artwalk. 

 

The event features a dozen art shows and exhibits on view at venues around downtown Pittsfield. Most of the art is on display throughout Dec.

 

During the event, participants will have the opportunity to meet the artists. Download the Downtown Pittsfield Inc. app from the Google Play or App Store to get a virtual walking tour. 

 

Participating venues include Beacon Cinema, Berkshire Art Center, Berkshire Museum, Clock Tower Artists, Hotel on North, Lichtenstein Center for the Arts, Soda Chef, and more.

 

For a complete list of participating venues and artists visit the Art Walk website.

 

Saturday 

 

Winter Wonderland Family Fun Day

Stockbridge Library

Time: 10 to 3 p.m. 

 

The library will have a youth craft table so children can decorate a snowflake, indoor winter games, and an outdoor StoryWalk through the decorated library garden walkway. At 10:45 a.m. there will be a winter-themed storytime. More information here. 

 

North Adams Farmers Market

85 Main St. 

Time: 9 to 1

 

Final indoor winter market of the year; winter markets run every first Saturday through May. Jams and jellies, handcrafted wool items, bagels and baked goods, jewelry, maple syrup, self-care and wellness, winter produce and meats, and much more. Continues $30 match program for SNAP users. 

 

 

Sunday 

 

Bebop with Poppy

65 Silver St, Sheffield

Time: noon

 

Drag Queen Poppy DaBubbly is collaborating with WitchSlapped and Big Elm to provide a music and music class the first sunday of every month. 

 

During the event families will explore essential development skills through dance, creative movement, and a story time.

 

More information here. 

 

Brunch with Santa

Wahconah Country Club, Dalton

Time: 10 to 1 p.m. 

 

Enjoy pancakes, eggs and more while you get professional pictures taken with Santa. There will be a cash bar. Brunch is $16 for adults and $8 for kids. Reservations for the brunch are needed. Make a reservation by emailing Jaceyanastasiophotography@gmail.com or Manager@wahconahcc.com

 

Professional Pictures With Santa is  available to both those attending the brunch and the outside community on a first come first serve basis.

 

More information here. 

 

Holiday Tea and Holiday-Inspired Readings

Herman Melville's historic Arrowhead, Pittsfield

Time: 3 p.m. 

 

Enjoy a cup of traditional Holiday Tea, provided by caterer Kate Baldwin, while you listen to holiday-inspired readings by local author Kevin O'Hara. 

 

Tickets cost $25 for members and $30 for non-members. Purchase tickets using the “Book” button on the Berkshire Historical Societies website. https://berkshirehistory.org/ Information here. 

 

Williamstown Theatre Festival Performance

Clark Art Institute, Williamstown

Time: 3 to 5 p.m. 

 

There will be a free performance of ‘Sammie And Dan: Singing and Holiday Cheer’ in the Clark’s auditorium, located in the Manton Research Center. More information here.

 

Multiple Days

 

Pittsfield Festive Frolic

Friday and Saturday 

 

This Friday and Saturday Downtown Pittsfield will be transformed into a festive wonderland full of holiday themed activities including the annual Park Square Tree Lighting on Friday at 6 p.m. 

 

During the two day frolic, local businesses will be hosting activities for all ages including free arts & craft opportunities, Pictures with Santa, a Hot Chocolate Bar and Photo Booth, and more.

 

On Friday, those 21 and over can participate in the Elf Invasion Pub Crawl. Dress up in Elf attire as you visit some of the local pubs and bars. Line-up here. 

 

Purchase an Elf ID in advance online or in person at 101 Restaurant & Bar on December 2 starting at 6:45 pm to secure an elf accessory and a Berkshire Mountain Distillers’ sample at each location. 

 

More information on the Pittsfield Frolic here. 

 

Williamstown Holiday Walk

Saturday and Sunday

 

The Williamstown Chamber of Commerce is hosting its 40th annual Holiday Walk weekend. This communitywide celebration features events at various venues including live musical performances, a market, drives, and more. 

Line-up here. 

 

Nightwood

The Mount, Lenox

Nov. 17 through Jan. 6

 

An innovative and immersive sound and light experience set against the backdrop of Edith Wharton's historic home. Wander the illuminated 3/4-mile route through the woods and gardens for an otherworldly experience that evokes wonder and awakens the imagination.

 

Children under 12 are free, children ages 13 to 18 are $12, and adults are $25. More information here.

 

Festival of Trees: NOSTALGIA

Berkshire Museum, Pittsfield

Nov. 18 to Jan. 7

 

Visit the museum and get into the holiday spirit with the decades-old celebration Festival of Trees which features trees decorated by community members, businesses, and institutions with ties to the community.

 

More information here.

 

Winterlights

Naumkeag, Stockbridge

 

Three of the Trustees of Reservations' properties will be decorated with holiday light displays, including Naumkeag. The immersive holiday light displays also feature festive music and seasonal treats. 

 

The event happens  Wednesdays through Sundays until January 6. More information here.