Rally the corgi has sniffed out the Christmas events for kids in Darien, Connecticut for 2026. Santa’s Letter Box opens on November 30 for wish lists, and An Old Fashion Holiday fills Tilley Pond Park with cookie decorating, crafts and a tree lighting on Saturday, December 5. We check every date on the host’s own website and link straight there. For the rest of the state, see our Connecticut Christmas events for kids guide.
What Rally found in Darien
- 2 Christmas events for kids in Darien
- An Old Fashion Holiday: Saturday, December 5, 2 to 5 pm, Tilley Pond Park, free
- Cookie decorating, crafts, ice sculptures and a tree lighting
- Santa’s Letter Box: November 30 to December 8
- Every date checked on the Town of Darien calendar on Nov 11
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Free Christmas events for kids in Darien
Holiday festival and tree lightingFree
An Old Fashion Holiday
- When: Saturday, December 5, 2026, 2 to 5 pm, with the tree lighting at the close
- Where: Tilley Pond Park, 40 West Avenue, Darien, CT 06820 (opens in maps)
- Cost: Free admission
- Ages: All ages
Expand to see the parent tip
Darien Parks & Recreation turns Tilley Pond Park into a holiday afternoon for the whole town, with cookie decorating, holiday crafts, an ice sculpture display and a small holiday market.
Families can stroll the pond paths between activities, and as the light fades the community gathers to switch on the holiday tree, the traditional finale of the day.
Parent tip: Arrive by 2 pm for the cookie decorating and crafts before lines build, and stay until about 5 pm for the tree lighting.
- Host
- Darien Parks & Recreation (opens in a new tab)
- Address
- Tilley Pond Park, 40 West Avenue, Darien, CT 06820 (opens in maps)
- Confirmed
- On the host’s page, checked
New Darien events every week
Rally researches Christmas events in Darien daily and updates this page with new events. Enter your email to get a weekly update with new events in Darien.
Free. Unsubscribe anytime. Privacy policy (opens in a new tab)
Rally’s Christmas research
Rally the corgi has 1 more Darien 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 Darien.
- Exclusive access to free events Find the free Christmas events in Darien 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
- 2 Free
Enter your email to get new Christmas events in Darien every week.
Letters to SantaFree
Santa’s Letter Box
- When: Monday, November 30 to Tuesday, December 8, 2026
- Where: Darien Parks & Recreation Office and Darien Sport Shop, Darien, CT 06820 (opens in maps)
- Cost: Free
- Ages: Kids
Expand to see the parent tip
Santa’s Letter Box gives Darien kids an official place to mail their wish lists straight to the North Pole.
Boxes sit at the Darien Parks & Recreation Office and the Darien Sport Shop, and December 8 is the last day to drop letters so Santa has time to write back before Christmas.
Parent tip: Put a return address on every letter so Santa’s reply can find its way home.
- Host
- Darien Parks & Recreation (opens in a new tab)
- Address
- Darien Parks & Recreation Office and Darien Sport Shop, Darien, CT 06820 (opens in maps)
- Confirmed
- On the host’s page, checked
New Darien events every week
Rally researches Christmas events in Darien daily and updates this page with new events. Enter your email to get a weekly update with new events in Darien.
Free. Unsubscribe anytime. Privacy policy (opens in a new tab)
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 Connecticut Christmas train rides page.
See every event on a December calendar
Plan your December
When each Darien Christmas event for kids happens
Have the kids write their letters early and drop them in Santa’s Letter Box by December 8, then spend the afternoon of December 5 at Tilley Pond Park and stay for the tree lighting.
- Santa’s Letter BoxDarien · Nov 30 to Dec 8
- An Old Fashion HolidayDarien · Dec 5
Looking further afield? Our Connecticut Christmas events for kids guide lists every confirmed event in the state, and we have city guides for Stamford, Fairfield, Bridgeport and Danbury. 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 Connecticut city.
Darien Christmas events for kids: questions parents ask
What are the best Christmas events for kids in Darien this year?
Rally Takes the Train has confirmed 2 Christmas events for kids in Darien for 2026, both from Darien Parks & Recreation: Santa’s Letter Box from November 30 and An Old Fashion Holiday on December 5.
When is An Old Fashion Holiday in 2026?
Saturday, December 5, 2026, from 2 to 5 pm at Tilley Pond Park, 40 West Avenue. Admission is free and the holiday tree is lit as the afternoon ends.
What do kids do at An Old Fashion Holiday?
Cookie decorating, holiday crafts, an ice sculpture display, a holiday market and a stroll around the pond before the tree lighting.
Where is Santa’s Letter Box in Darien?
At the Darien Parks & Recreation Office and the Darien Sport Shop from November 30 to December 8, 2026. December 8 is the last day for letters.
Who do I contact about Darien holiday events?
Darien Parks & Recreation at parkrec@darienct.gov.
Are there Christmas train rides for kids in Connecticut?
Yes. Santa trains and holiday train rides have their own guide: Rally Takes the Train’s Connecticut 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 Darien 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.