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Local Berkshire Holiday Fun Events

Thanksgiving, Christmas, Hannukah, New Years and More

By Berkshires Macaroni Kid November 28, 2023

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. Masks are required and social distancing is observed. 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! The display is nightly 4-9 p.m., Nov. 24 through Jan. 1. 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: NOSTALGIA
December 1

Norman Rockwell: Winter Wonderland (Stockbridge) ❄️

Tree Lighting (Lenox ) πŸ•― πŸŽ„ πŸŽ…

Free Admission to the Festival of Trees! (Pittsfield) πŸ•―πŸŽ„

The Polar Express at The Beacon (Pittsfield) ❄️

Holiday Tree Lighting Ceremony (Pittsfield) πŸŽ„ πŸŽ…

Free Hot Chocolate & Photo Ops with the Grinch (Pittsfield) ❄️

Tree Lighting (Lenox ) πŸ•― πŸŽ„ πŸŽ…

Angels of Remembrance Holiday Tree Lighting (Lee) πŸ•―πŸŽ„

40th Annual Holiday Walk (Williamstown) πŸ•―πŸŒ² πŸŽ…

First Friday Festivities (North Adams) πŸ•―πŸŽ„πŸŽ…

December 2

40th Annual Holiday Walk (Williamstown) πŸ•―πŸŒ² πŸŽ…

Grinch Brunch (Pittsfield) πŸŽ…

C.A.R.E.S. Annual Holiday Party (Great Barrington) ❄️ πŸŽ…

Holiday Card Making Drop-in (Pittsfield) ❄️

Festive Frolic LEGO Drop-in at Bottomless Bricks (Pittsfield) ❄️

Winter Family-Fun Weekend (Stockbridge) ❄️

Family Ornament Making at Artsy Avenue (North Adams) ❄️

Winter Wonderland Walkway (Stockbridge) β„οΈπŸŽ„

Annual New Marlborough Central Elementary School Holiday Fair (New Marlborough) ❄️

Christmas Photoshoot With Horse or Donkey (South Egremont) ❄️ πŸŽ…

Photos with Santa at The Beacon Cinema (Pittsfield) β„οΈπŸŽ…

Norman Rockwell: Winter Wonderland (Stockbridge) ❄️

The Polar Express at The Beacon (Pittsfield) ❄️

34th Annual Main Street at Christmas (Stockbridge) πŸ•― ❄️ πŸŽ… πŸŽ„

Festive Frolic Junior (Pittsfield) πŸŽ„πŸŽ…β„οΈ

The Nutcracker (Pittsfield) ❄️

December 3

9th Annual Eagle Brass Ensemble Holiday Concert (Adams) πŸ•―

40th Annual Holiday Walk (Williamstown) πŸ•―πŸŒ² πŸŽ…

Annual Festival of Trees & Town Tree Lighting (Cheshire) πŸ•―πŸŽ„πŸŽ…

Bebop with Poppy (Pittsfield)

Brunch with Santa (Dalton)πŸŽ…

The Polar Express at The Beacon (Pittsfield) ❄️

Norman Rockwell: Winter Wonderland (Stockbridge) ❄️

Bebop with Poppy (Sheffield)

Winter Wonderland Walkway (Stockbridge) β„οΈπŸŽ„

34th Annual Main Street at Christmas (Stockbridge) πŸ•― ❄️ πŸŽ… πŸŽ„

The Nutcracker (Pittsfield) ❄️

December 8

Santa's Trains At Look Park (Florence)πŸŽ…

A Christmas Carol (Stockbridge) πŸ•―β„οΈ

Photos with Santa Holiday Event (Cheshire) ❄️ πŸŽ…

Albany Berkshire Ballet Nutcracker Excerpts (Pittsfield) ❄️

December 9

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

Santa's Trains At Look Park (Florence)πŸŽ…

Holiday Shop, Sip & Stroll (Great Barrington) β„οΈπŸŽ„πŸŽ…

Santa At Chocolate Springs (Lenox) β„οΈπŸŽ…

Holiday Shindy (Pittsfield) ❄️

Charlie's Trains (Great Barrington) ❄️

Gingerbread House Decorating (Lenox) ❄️

Holly Jolly Holiday Brook Farm (Dalton) ❄️ πŸŽ…

Mickey's Christmas Carol (Great Barrington)πŸŽ„

Light Up the Holidays (Dalton) πŸ•―πŸŽ„πŸŽ…

A Night in Bethlehem (Lenox) πŸ•―

A Christmas Carol (Stockbridge) πŸ•―β„οΈ

December 10

Holiday Music Tour (North Adams) ❄️

Donuts With Santa (Dalton) πŸŽ…

Charlie's Trains (Great Barrington) ❄️

Celebrate Chanukah at Nightwood (Lenox) πŸ•― πŸ•Ž

Mutts Gone Nuts: Santa Paws (Pittsfield) ❄️

Cantame Un Cuento, Sing Me A Story (Lenox)

Breakfast With Santa (Adams) πŸŽ…

Santa At Chocolate Springs (Lenox) β„οΈπŸŽ…

Santa's Trains At Look Park (Florence)πŸŽ…

A Night in Bethlehem (Lenox) πŸ•―

A Christmas Carol (Stockbridge) πŸ•―β„οΈ

December 15

Santa's Trains At Look Park (Florence)πŸŽ…

Radiant Nights (Hancock) πŸ•―β„οΈ

The Muppet Christmas Carol (Great Barrington)πŸŽ„

A Christmas Carol (Stockbridge) πŸ•―β„οΈ

December 16

Norman Rockwell: Winter Wonderland (Stockbridge) ❄️

Santa at the Gazebo (Cummington) πŸŽ…β„οΈ

Berkshire Lyric Presents: Home for Christmas 2023 Concert (Stockbridge) πŸ•―β„οΈ

BAC Drop-In Art Making (Pittsfield)

Crissey Farm Presents Cookies & Cocoa with the Clauses (Great Barrington) β„οΈπŸŽ…

Cookie Decorating for Kids & Teens! (Lenox) ❄️

Santa in the Berkshires (Pittsfield) πŸŽ…

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

Charlie's Trains (Great Barrington) ❄️

Santa's Trains At Look Park (Florence)πŸŽ…

A Christmas Carol (Stockbridge) πŸ•―β„οΈ

December 17

Norman Rockwell: Winter Wonderland (Stockbridge) ❄️

Radiant Nights (Hancock) πŸ•―β„οΈ

Charlie's Trains (Great Barrington) ❄️

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

A Christmas Carol (Stockbridge) πŸ•―β„οΈ

December 22

Norman Rockwell: Winter Wonderland (Stockbridge) ❄️

Santa's Trains At Look Park (Florence)πŸŽ…

Radiant Nights (Hancock) πŸ•―β„οΈ

A Christmas Carol (Stockbridge) πŸ•―β„οΈ

It's A Wonderful Life (Great Barrington)πŸŽ„

The Wizards of Winter (Pittsfield) ❄️

December 23

Norman Rockwell: Winter Wonderland (Stockbridge) ❄️

Santa's Trains At Look Park (Florence)πŸŽ…

Holiday Cookie Walk (Hinsdale) ❄️

Radiant Nights (Hancock) πŸ•―β„οΈ

A Christmas Carol (Stockbridge) πŸ•―β„οΈ

December 24

A Christmas Carol (Stockbridge) πŸ•―β„οΈ

Radiant Nights (Hancock) πŸ•―β„οΈ

December 29

Kids Can Cook (Williamstown)

Radiant Nights (Hancock) πŸ•―β„οΈ

A Christmas Carol (Stockbridge) πŸ•―β„οΈ

December 30

The MET: The Magic Flute (Williamstown) ❄️

Radiant Nights (Hancock) πŸ•―β„οΈ

Magic By George (Pittsfield)

A Christmas Carol (Stockbridge) πŸ•―β„οΈ

December 31