things to do near you

Things to do in Western Mass and the Berkshires this fall and Christmas

Okay so this is everything going on out in Western Mass and the Berkshires this fall and then Christmas, the Big E, then Stockbridge turning into the Norman Rockwell painting and the lights at Naumkeag, all in one place. Tap anything you want to do and I'll put it on your bucket list for you, and if you want the addresses and the dates and all that, "make my plan" builds it and puts it on your calendar.

Last updated September 28, 2026. Dates come from each event's own page and I recheck them all season, but tap the link and double check before you load up the car.

Fall Christmas Any weekend More Massachusetts areas
the big stuff

Fall in Western Mass and the Berkshires1 things

The ones people drive in from other counties for. Most of them run the whole season, so you don't have to pick a weekend yet.

Little kidsTeens
The Big EWest Springfield
September 18 to October 4
The giant fair for all six New England states, with food from every one of them.
town by town

The little stuff, by town0 things

The city Halloween parties and the trunk or treats and the free stuff. Cities post their 2026 dates late, so anything marked "check the date" gets fixed the second it's announced.

The cities post these in early November. Check back.

and the stuff at home

For the rest of your list

These don't need an address, tap them and they go on your list with everything else.

lights and trains

Christmas in Western Mass and the Berkshires2 things

Stockbridge does its Main Street weekend the first weekend in December, and the inns fill up fast.

Little kids
Stockbridge Main Street at ChristmasStockbridge
the first weekend in December · check the date
They close Main Street and park vintage cars along it to recreate the Norman Rockwell painting, with wagon rides and Santa.
Little kids
Winterlights at NaumkeagStockbridge
Wednesday to Sunday nights, late November into early January · check the date
An old estate garden full of lights and music in the snow.
town by town

Town Christmas stuff

The town stuff, and I'll add the tree lightings as the cities post them in November.

Christmas in Lenox

Sells outLittle kids
Tinseliner Christmas Train
late November to mid December · check the date
A Christmas train ride with carols and Santa on board.
and the stuff at home

For the rest of your Christmas list

This is the at-home stuff, tap them and they go on your list with the lights and the train.

put it on the wall

Turn your Christmas picks into a real bucket list

Tap the lights and the trains and the town stuff you want and pick the Christmas design you like, and I'll hold onto your picks. The Christmas lists are coming soon, and the second they're up your picks drop straight into the slots.

See the Christmas designs (coming soon)
no tickets, no dates

Good any weekend0 things

The stuff that doesn't need a date, for the Saturday when nothing's going on.

people ask me

Western Mass and the Berkshires fall and Christmas questions

When is Stockbridge Main Street at Christmas?

The first weekend in December, with the vintage cars on Main Street on Sunday.

When is the Big E in 2026?

September 18 to October 4, 2026.

Amy
who's writing this

Hi, I'm Amy.

We roadschool six kids out of a van. I'm just a mom with a Ford Transit and a lot of opinions about corn mazes, so if something on here is wrong, or your town's party is missing, email me at hello@bellebucket.com and I'll fix it.

put it on the wall

Turn your picks into a real bucket list

Tap the ones you want and I'll drop them onto whichever fall design you pick, then you add your own stuff (birthdays, carving pumpkins, whatever your family does). It prints big, like 24x36 big, and it hangs on the wall all season.

See the fall designs

If you run one of these events and want it on here, or something's off, email hello@bellebucket.com. I'd love to have you.

0 on your list