Rally the corgi has sniffed out the Christmas events for kids in Pittsfield for 2026. The Berkshire Museum’s Festival of Trees: Let’s Play runs from November 20 into January, and on December 9 and 10 the city’s North Pole Calling Program has Santa phone Pittsfield kids at home. We check every date on the host’s own website and link straight there. For the rest of the state, see our Massachusetts Christmas events for kids guide.
What Rally found in Pittsfield
- 2 Christmas events for kids in Pittsfield
- Festival of Trees: Let’s Play: Berkshire Museum, November 20 to January 10
- North Pole Calling: Santa calls kids December 9 and 10, free
- Santa call forms due Tuesday, December 8
- Every date checked on host sites on Nov 11
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Free Christmas events for kids in Pittsfield
Phone call from SantaFree
North Pole Calling Program
- When: Wednesday, December 9 and Thursday, December 10, 2026, calls between 5 and 7:30 pm; forms due Tuesday, December 8
- Where: Calls placed to your home, run from Pittsfield City Hall, 70 Allen Street, Pittsfield, MA 01201 (opens in maps)
- Cost: Free
- Ages: Pittsfield children in Pre-K through grade 2
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For the 45th year, the City of Pittsfield’s recreation program arranges for Santa to phone Pittsfield children at home on two December evenings.
Sign-up forms go home through schools for kids in Pre-K through second grade, and fillable forms are also on the city website and at City Hall. Older kids who still believe are welcome too.
Parent tip: Note something specific on the form, like a pet’s name or a recent milestone, so Santa’s call feels personal. Do not send forms to school.
New Pittsfield events every week
Rally researches Christmas events in Pittsfield daily and updates this page with new events. Enter your email to get a weekly update with new events in Pittsfield.
Free. Unsubscribe anytime. Privacy policy (opens in a new tab)
Rally’s Christmas research
Rally the corgi has 1 more Pittsfield event researched for you.
- New events every week We research new events daily and send you one email a week with the new ones we find in Pittsfield.
- Exclusive access to free events Find the free Christmas events in Pittsfield before they fill up.
- Unlock the filters Find Santa visits, free events and weekend plans in one tap.
- Rally’s Christmas Eve Express and a free advent calendar Get early access to Rally the corgi’s Christmas Eve tracker, plus a free digital advent calendar to count down to Christmas.
- One-tap add to calendar Save any event to your Google, Apple or Outlook calendar so you never miss it.
Coming up on this page
- 1 Santa
- 1 Lights
- 1 Free
Enter your email to get new Christmas events in Pittsfield every week.
Ticketed and paid Christmas events for kids in Pittsfield
Admission, tickets or a fee apply. Where a host has not posted a price yet, the listing says so.
Event hosts: free events are listed first. The #1 spot puts your event at the top of this page.Inquire about the #1 spotAdd your event for free
Museum tree festival
Festival of Trees: Let’s Play
- When: November 20, 2026 to January 10, 2027, during museum hours (Friday to Wednesday, 10 am to 5 pm; closed Thursdays)
- Where: Berkshire Museum, Crane Room, 39 South St, Pittsfield, MA 01201 (opens in maps)
- Cost: Included with museum admission; tickets through the Berkshire Museum
- Ages: All ages
Expand to see the parent tip
The Berkshire Museum’s Festival of Trees returns to its newly renovated building with a theme of play, filling the Crane Room with trees decorated by local businesses, groups and families.
This year’s trees riff on board games, sports, video games and music, and the museum adds special programs through the season, so it pairs easily with a look at the new Feigenbaum Aquarium.
Parent tip: The museum is closed on Thursdays, so plan your visit for another day and check the events page for festival programs.
- Host
- Berkshire Museum (opens in a new tab)
- Address
- Berkshire Museum, Crane Room, 39 South St, Pittsfield, MA 01201 (opens in maps)
- Confirmed
- On the host’s page, checked
New Pittsfield events every week
Rally researches Christmas events in Pittsfield daily and updates this page with new events. Enter your email to get a weekly update with new events in Pittsfield.
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We check every event above on the host’s own page for the date, time and cost, plus the things parents ask about, like sign-ups and ages. Looking for a Santa train instead? Those are on our Massachusetts Christmas train rides page.
See every event on a December calendar
Plan your December
When each Pittsfield Christmas event for kids happens
Send in the North Pole Calling form before December 8, then visit the Festival of Trees any day except Thursday through January 10.
- Festival of Trees: Let’s PlayPittsfield · Nov 20 to Jan 10
- North Pole Calling ProgramPittsfield · Dec 9 to Dec 10
Looking further afield? Our Massachusetts Christmas events for kids guide lists every confirmed event in the state, and we have city guides for Amherst, Springfield, Auburn and Worcester. The national search sorts every event by distance from your town.
A story for the drive home
A morning with Santa or an evening of holiday stories tends to end the same way: tired kids, a long drive and one more book before bed. Our picture book follows Rally the corgi on his first train ride to see his grand-paw-rents, and every page is painted by hand. If your family is spending December missing someone, it was written for that too. For the car, print our free corgi and train coloring pages.
A bedtime story after seeing SantaRally Takes the Train is a five-minute rhyming picture book about a corgi’s first ride on a California train, hand-painted in watercolor. $16.99 on Amazon, ages 0 to 8.
Buy on AmazonKeep the Christmas magic going: track Rally the corgi on Christmas Eve, print free Christmas coloring pages, learn how to say Merry Christmas in 100+ languages, find train museums to visit with kids, or browse Christmas events in every Massachusetts city.
Pittsfield Christmas events for kids: questions parents ask
What are the best Christmas events for kids in Pittsfield this year?
Rally Takes the Train has confirmed 2 Christmas events for kids in Pittsfield for 2026: Festival of Trees: Let’s Play at the Berkshire Museum and the City of Pittsfield’s North Pole Calling Program.
When is the Berkshire Museum Festival of Trees in 2026?
November 20, 2026, through January 10, 2027, in the Crane Room at 39 South Street, open during museum hours. The museum is closed on Thursdays.
How does the Pittsfield North Pole Calling Program work?
Parents fill out a form, and Santa phones Pittsfield children in Pre-K through grade 2 at home on December 9 or 10, 2026, between 5 and 7:30 pm. Forms are due Tuesday, December 8.
Where do I get a North Pole Calling form?
Forms go home with Pittsfield students by November 16, are available as fillable forms on the city website, and are at the City Clerk’s Office and Community Development office at City Hall, 70 Allen Street.
Who do I contact about Pittsfield holiday events?
Jennifer VanBramer, Recreation and Special Events Coordinator, at jvanbramer@pittsfieldma.gov for North Pole Calling, and the Berkshire Museum at development@berkshiremuseum.org for Festival of Trees.
Are there Christmas train rides for kids in Massachusetts?
Yes. Santa trains and holiday train rides have their own guide: Rally Takes the Train’s Massachusetts Christmas train rides page.
How do you confirm these events?
We list an event only after we find this season’s date on the host’s own website or an official city or tourism calendar. We last checked Pittsfield on November 11, 2026. Rally is also contacting each organizer to confirm details like parking, restrooms and bad-weather plans.
Event names belong to their hosts. Rally Takes the Train is a family picture book and is not affiliated with, sponsored by or endorsed by any host listed here. Confirm dates, times and prices on each host’s own site before you go.