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Local Berkshire Holiday Fun Events

Thanksgiving, Christmas, Hannukah, New Years and More

By Berkshires Macaroni Kid December 9, 2024

Family-friendly Thanksgiving, Christmas, Hanukkah and other holiday events in the Berkshires are filling up our CALENDARS and we've got your complete listings below. New events are being added daily. 

Do you have an event to list? SUBMIT IT HERE

You can also search our calendars to find Berkshire County Holiday Events using the simple steps below:

From Mobile: Go to the calendar on the bottom of the homepage and CLICK ON MORE EVENTS. From that page SEARCH HOLIDAY FUN in Categories.

On Desktop: Use the SEARCH bar at the top of any page and use any of the emoji's below to search for specific events:

❄️ πŸ•―Local Holiday Family Fun
πŸŽ…πŸΌ Santa Sightings
πŸŽ„Tree Lightings
πŸ•Ž Hanukkah Celebrations

Ongoing Holiday Events
  • Winterlights at Naumkeag, two of Naumkeag's beautiful garden properties sparkle with thousands of shimmering, artfully designed holiday lights. Bring the whole family for a magical, fun, and safe outdoor experience – with food, refreshments, and more. Runs Tuesdays-Sundays, 4:30-8:30 p.m., Nov. 24 through Jan. 6. Naumkeag, 5 Prospect Hill Road, Stockbridge. thetrustees.org. 
  • Nightwood at the Mount, a sound and light experience that transforms the property into a fantastical winter landscape. Inspired by the natural beauty and architecture of The Mount, NightWood’s sculptural elements, lighting, and original music evoke elements of mystery and whimsy. Runs Thursdays through Sundays Nov. 17 through Jan. 6, 5-8 p.m. The Mount, 2 Plunkett St., Lenox. edithwharton.org.
  • Berkshire Scenic Railway's Tinseliner Train Ride, Friday-Sunday, beginning Nov. 24 and running through Dec. 17. Get your tickets HERE. Departs from the Adams Station, 4 Hoosac St., Adams, plan to park at the Visitor's Center. 
  • Ventfort Hall Holiday House TourExperience the historic property all dressed up for the holidays. Self-guided tours are offered daily on the hour from 10 a.m. to 3 p.m. Ventfort Hall & Gilded Mansion, 104 Walker St., Lenox, gildedage.org
  • Santa Letters, Write a letter to Santa and drop it in the holiday mailbox located in front of the Dalton Police Station between Nov. 24 and Dec. 15. Dalton Police Station, Main Street, Dalton. 
  • Winter Wonderland Walkway, Stroll through the Holiday Tree walkway at the Stockbridge Library and take in the festive lights. Downtown Stockbridge., stockbridgechamber.org
  • Bright Nights at Forest ParkBright Nights is the Northeast's premier holiday lighting experience. It features many scenes created by hundreds of pieces along a three-mile drive. They include Seuss Land, North Pole Village, Toy Land, Winter Woods where the deer leap over the road, Everett Barney Mansion, Jurassic World and so many more. Forest Park, 300 Sumner Ave., Springfield. brightnights.org
  • Look Park Holiday Lights DisplayCome enjoy the magic of the season by taking a trip around Look Park for our Holiday Light Display. Wave to the friendly dragon, imagine a princess getting ready for a ball in her light-up castle, and sing some carols with your family while you drive around the park! Entrance is free for all; donations are welcome! Look Park, 300 North Main Street, Florence
  • LuminNAMA!, starting Nov. 22nd, stroll through downtown North Adams and take in the downtown businesses adorned in lights along with fantastical winter displays designed by local artists. On display through Jan. 1st. luminama.com
  • Festival of Trees: AQUATICA
December 13

An Old Fashioned Christmas (Great Barrington) ❄️

Radiant Nights (Hancock) πŸ•―β„οΈ

Parents Night Out! (Stockbridge)

Berkshire Lyric Presents: Love's Pure Light (Pittsfield) πŸ•―οΈ

December 14

A Morning with Santa & Mrs. Claus (North Adams)πŸŽ…

An Old Fashioned Christmas (Great Barrington) ❄️

Moana 2 (Williamstown)

Gingerbread House STEAM Events (Adams) ❄️

Computer Science (Richmond)

Kids Concerts with Terry A La Berry and Friends (Pittsfield)

Tree Lighting, Fireworks, Holiday Shop, Sip, & Stroll (Great Barrington)πŸŽ„πŸŽ…πŸ•Ž

Radiant Nights (Hancock) πŸ•―β„οΈ

Lee's Second Saturday Gym Nights: Matball and Spud (Lee)

Festival of Trees (Hinsdale) πŸŽ„β„οΈπŸŽ…

December 15

An Old Fashioned Christmas (Great Barrington) ❄️

Silent Book Club (Pittsfield)

Festival of Trees (Hinsdale) πŸŽ„β„οΈπŸŽ…

Berkshire Lyric Presents: Love's Pure Light (Great Barrington) πŸ•―οΈ

Radiant Nights (Hancock) πŸ•―β„οΈ

December 20

Tweens & Teens Drop-In Craft (Stockbridge) ❄️

Teen Time @ Mason: Jigsaw Puzzle & Snacks (Great Barrington)

An Old Fashioned Christmas (Great Barrington) ❄️

Victorian Puzzle Purse Family Craft (Stockbridge) ❄️

Radiant Nights (Hancock) πŸ•―β„οΈ

December 21

Kidspace Storytime (North Adams)

Holiday Crafts at Lee Library (Lee)

Annual Adams Scavenger Hunt (Adams)

Create a Bookmark (Williamstown) ❄️

Berkshire Lyric Presents: The Very Best Time of the Year (Stockbridge) ❄️ πŸŽ…

Festival of Lights Walk (Lanesborough) ❄️

December 22

Radiant Nights (Hancock) πŸ•―β„οΈ

An Old Fashioned Christmas (Great Barrington) ❄️

December 23

Norman Rockwell Museum Holiday Week Programs (Stockbridge) ❄️

Library Mini Golf (Lee)

Movies at the Milne: The Wild Robot (Williamstown)

Afternoon Crafts and Story (Lee)

December 26

Norman Rockwell Museum Holiday Week Programs (Stockbridge) ❄️

Explore the Thingdom! (Williamstown)

December 27

Norman Rockwell Museum Holiday Week Programs (Stockbridge) ❄️

Family Movie Featuring Frozen (Stockbridge) ❄️

Radiant Nights (Hancock) πŸ•―β„οΈ

December 28

Parent & Me Art Meetup (Pittsfield)

Explore the Thingdom! (Williamstown)

Norman Rockwell Museum Holiday Week Programs (Stockbridge) ❄️

Radiant Nights (Hancock) πŸ•―β„οΈ