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Santa Sightings In and Around the Berkshires

We've got an extensive list of where you can find Santa in Berkshire County this holiday season

By Berkshires Macaroni Kid November 18, 2023

Santa Claus is coming to the Berkshires and we've been tracking him (and Mrs. Claus) for you, so you'll know just where to find him with your cameras and children's wish lists in hand. From regular stops to single-day visits, we're keeping track of where to see Santa in Berkshire County this season. Have you had a Santa sighting? Please let us know at taylors@macaronikid.com and we will add it to our list.

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We are updating this guide daily so be sure to check back!


Ongoing Sightings

Berkshire Scenic Railway Museum Santa's Mail Express Trains: 3 Hoosac St., Adams

The Hoosac Valley Train Rides will once again deck the halls for special holiday train rides on weekends beginning Nov. 24 and Santa always makes an appearance. Train rides will run Friday-Sunday, Nov. 24-Dec. 17th.

Yankee Candle, 25 Greenfield Road, South Deerfield

If you're up for a road trip, Santa spends a great deal of time at the Yankee Candle Village in Deerfield, and a day at Yankee Candle could even put Scrooge in the holiday spirit. This year experience a virtual Santa Experience like no other. Runs Nov. 3-Dec. 23


Single Event Sightings 

North Adams Tree Lighting (North Adams) πŸŽ„πŸŽ…November 22, 2023

Santa’s Arrival to Lanesborough Local (Lanesborough) πŸŽ…November 25, 2023

Santa in the Berkshires (Pittsfield) πŸŽ…November 25, 2023

Adams Holly Days (Adams) πŸŽ„ πŸŽ…November 26, 2023

First Friday Festivities (North Adams) πŸ•―πŸŽ„πŸŽ…December 1, 2023

Tree Lighting (Lenox ) πŸ•― πŸŽ„ πŸŽ…December 1, 2023

Holiday Tree Lighting Ceremony (Pittsfield) πŸŽ„ πŸŽ…December 1, 2023 

40th Annual Holiday Walk (Williamstown) πŸ•―πŸŒ² πŸŽ…December 2, 2023

Grinch Brunch (Pittsfield) πŸŽ…December 2, 2023

34th Annual Main Street at Christmas (Stockbridge) πŸ•― ❄️ πŸŽ… πŸŽ„December 2, 2023

Photos with Santa at The Beacon Cinema (Pittsfield) β„οΈπŸŽ…December 2, 2023

Festive Frolic Junior (Pittsfield) πŸŽ„πŸŽ…β„οΈDecember 2, 2023

Christmas Photoshoot With Horse or Donkey (South Egremont) ❄️ πŸŽ…December 2, 2023

C.A.R.E.S. Annual Holiday Party (Great Barrington) ❄️ πŸŽ…December 2, 2023

Brunch with Santa (Dalton)πŸŽ…December 3, 2023

Annual Festival of Trees & Town Tree Lighting (Cheshire) πŸ•―πŸŽ„πŸŽ…December 3, 2023

34th Annual Main Street at Christmas (Stockbridge) πŸ•― ❄️ πŸŽ… πŸŽ„December 3, 2023

Sparkles Parade (West Stockbridge) πŸŽ„ ❄️ πŸŽ…

40th Annual Holiday Walk (Williamstown) πŸ•―πŸŒ² πŸŽ…December 3, 2023

Photos with Santa Holiday Event (Cheshire) ❄️ πŸŽ…December 8, 2023

Santa's Trains At Look Park (Florence)πŸŽ…December 8, 2023

Holly Jolly Holiday Brook Farm (Dalton) ❄️ πŸŽ…December 9, 2023

Holiday Shop, Sip & Stroll (Great Barrington) β„οΈπŸŽ„πŸŽ…December 9, 2023

Santa At Chocolate Springs (Lenox) β„οΈπŸŽ…December 9, 2023

Light Up the Holidays (Dalton) πŸ•―πŸŽ„πŸŽ…December 9, 2023

Donuts With Santa (Dalton) πŸŽ…December 10, 2023

Breakfast With Santa (Adams) πŸŽ…December 10, 2023

Santa At Chocolate Springs (Lenox) β„οΈπŸŽ…December 10, 2023

Crissey Farm Presents Cookies & Cocoa with the Clauses (Great Barrington) β„οΈπŸŽ…December 16, 2023

Santa at the Gazebo (Cummington) πŸŽ…β„οΈDecember 16, 2023

Santa in the Berkshires (Pittsfield) πŸŽ…December 16, 2023

Festival of Trees (Hinsdale) πŸŽ„β„οΈπŸŽ…December 16, 2023

Festival of Trees (Hinsdale) πŸŽ„β„οΈπŸŽ…December 17, 2023 

✨ MORE COMING SOON — stay tuned for more as we receive them.✨

Want to stay on top of all the latest and greatest happenings for families in the Berkshires? Sign up to receive your free weekly newsletter HERE.