Christmas Events for Kids in Fairfield, CT (2026)

Christmas Events for Kids
Written by Kelsey Cecil

Updated 4 min read

Rally the corgi has sniffed out the best Christmas events for kids in Fairfield, CT for 2026, and here is what he found: 4 family events. The magic runs from November 14 (Meet Santa at the Holiday Pop-Up Market) through December 29, with Holiday Express Train Show Grand Opening (November 28), The Christmas Express (from November 28) and Santa Visits the Holiday Express Train Show (Members Only) (December 5) along the way. We check every date on the host’s own website, and each listing links straight there. For the rest of the state, see our Connecticut Christmas events for kids guide.

What Rally found in Fairfield

  • 4 Christmas events for kids in Fairfield
  • Meet Santa: Meet Santa at the Holiday Pop-Up Market (November 14) and Santa Visits the Holiday Express Train Show (Members Only) (December 5)
  • Also on the list: 1 Christmas show and 1 Christmas market
  • Season: November 14 (Meet Santa at the Holiday Pop-Up Market) to December 29 (The Christmas Express)
  • Every date checked on the host’s own site on Nov 10

Ticketed and paid Christmas events for kids in Fairfield

Admission, tickets or a fee apply. Where a host has not posted a price yet, the listing says so.

Santa visit

Meet Santa at the Holiday Pop-Up Market

Expand to see the parent tip

Santa sets up at the Fairfield Museum during its 12th annual Holiday Pop-Up Market, a shopping morning of handmade goods, original artwork and one-off gifts. Students from the Fairfield Ludlowe High School ASL Club will be beside him to help children and Santa talk in American Sign Language.

Santa is there on Saturday, November 14, 2026, from 10:00 am to 12:30 pm. Children 12 and under visit free, adults pay $5 at the door by cash or card, and every paid admission is entered to win a Museum Shop gift bag that includes a one-year family membership. Proceeds go to the museum's education programs and free community events.

Parent tip: Santa has only two and a half hours here, so see him first and browse the stalls afterward. If your child signs, this is a visit where Santa has ASL helpers right beside him.

Host
Fairfield Museum and History Center (opens in a new tab)
Address
Fairfield Museum and History Center, 370 Beach Road, Fairfield, CT 06824 (opens in maps)
Confirmed
On the host’s page, checked
See dates and detailsfrom Fairfield Museum and History Center (opens in a new tab)

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Rally’s Christmas research

Rally the corgi has 3 more Fairfield events researched for you.

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Coming up on this page

  • 3 Trains
  • 2 Santa
  • 1 Shows
  • 1 Markets

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Holiday event

Holiday Express Train Show Grand Opening

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This is the first evening of the museum's Holiday Express Train Show, timed so families can come in and warm up after the town's tree and menorah lighting ceremony. Visitors get an early look at the model train displays, which are supported by the Connecticut G-Scalers Club and the Housatonic Model Railroad Club.

The opening runs Saturday, November 28, 2026, from 5:00 to 7:00 pm at 370 Beach Road. Entry is $3 per person or $10 for a family of four. The museum's page does not mention advance tickets.

Parent tip: Since the opening follows the outdoor lighting ceremony, many families are likely to head over at the same moment. Waiting twenty minutes can mean more room at the train tables, and the family rate saves $2 for a group of four.

Host
Fairfield Museum and History Center (opens in a new tab)
Address
Fairfield Museum and History Center, 370 Beach Road, Fairfield, CT 06824 (opens in maps)
Confirmed
On the host’s page, checked
See dates and detailsfrom Fairfield Museum and History Center (opens in a new tab)

New Fairfield events every week

Rally researches Christmas events in Fairfield daily and updates this page with new events. Enter your email to get a weekly update with new events in Fairfield.

Free. Unsubscribe anytime. Privacy policy (opens in a new tab)

Holiday show

The Christmas Express

  • When: Sat November 28 (10:30 am), Sat November 28 (1 pm), Sat December 5 (10:30 am), Sat December 5 (1 pm), Sun December 6 (2:30 pm), Sun December 6 (5 pm), Sat December 12 (2:30 pm), Sat December 12 (5 pm), Sat December 19 (10:30 am), Sat December 19 (1 pm), Sun December 20 (2:30 pm), Sun December 20 (5 pm), Sat December 26 (1 pm), Mon December 28 (1 pm), Tue December 29 (10:30 am) and Tue December 29 (1 pm), 2026 (16 performances on select dates; doors open 30 minutes before each start time and the show runs about 60 to 65 minutes)
  • Where: The Warehouse at FTC, 70 Sanford St, Fairfield, CT 06824 (opens in maps)
  • Cost: Tickets required for every guest; no price listed on the organizer's page
  • Ages: Made for preschool and elementary ages, open to all
Expand to see the parent tip

The Christmas Express is a musical of about an hour for young audiences, in which a train ride has to rescue the magic of Christmas, set to a mix of familiar and newer holiday songs. It plays at The Warehouse at FTC, a short walk from the Fairfield train station, and families sit at reserved cabaret tables where they can eat a picnic brought from home.

There are 16 performances between November 28 and December 29, 2026, with start times of 10:30 am, 1:00 pm, 2:30 pm or 5:00 pm depending on the day, and doors open 30 minutes ahead. Every guest needs a ticket and a reserved seat, including babies who will sit on a lap. Seats are sold one by one at tables of four or five, and the page does not show prices.

Parent tip: Tables cannot be moved or joined, and empty seats at yours can be sold to another family, so book early or buy the whole table if you want it to yourselves. Station parking across the street is free on weekends but has a two-hour limit before 5:00 pm for the Monday and Tuesday shows on December 28 and 29.

Host
Fairfield Theatre Company (opens in a new tab)
Address
The Warehouse at FTC, 70 Sanford St, Fairfield, CT 06824 (opens in maps)
Confirmed
On the host’s page, checked
See dates and detailsfrom Fairfield Theatre Company (opens in a new tab)

New Fairfield events every week

Rally researches Christmas events in Fairfield daily and updates this page with new events. Enter your email to get a weekly update with new events in Fairfield.

Free. Unsubscribe anytime. Privacy policy (opens in a new tab)

Santa visit

Santa Visits the Holiday Express Train Show (Members Only)

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Fairfield Museum members get the first half hour with Santa inside the Holiday Express Train Show before the public session begins. Families take their own pictures with him in front of a special display among the model trains, and students from the Fairfield Ludlowe High School ASL Club help children and Santa communicate in American Sign Language.

This session is Saturday, December 5, 2026, from 9:30 to 10:00 am and is open to museum members only. The page lists it as free with museum admission and does not mention sign-up.

Parent tip: Thirty minutes goes quickly, so be at the door at 9:30 with your phone or camera ready, since there is no photographer and you take your own pictures. Families who are not members can come to the public session that starts at 10:00.

Host
Fairfield Museum and History Center (opens in a new tab)
Address
Fairfield Museum and History Center, 370 Beach Road, Fairfield, CT 06824 (opens in maps)
Confirmed
On the host’s page, checked
See dates and detailsfrom Fairfield Museum and History Center (opens in a new tab)

New Fairfield events every week

Rally researches Christmas events in Fairfield daily and updates this page with new events. Enter your email to get a weekly update with new events in Fairfield.

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 Fairfield Christmas event for kids happens

The first is Meet Santa at the Holiday Pop-Up Market in Fairfield on November 14; the last runs to December 29. Each bar spans an event’s dates, not every hour in them, so check the host’s page for times.

Looking further afield? Our Connecticut Christmas events for kids guide lists every event we have found in the state, and we have city guides for Bridgeport, Stamford, New Haven and Woodbury. 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.

Rally Takes the Train book cover: a watercolor corgi peeking from a red train

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 Amazon (opens in a new tab)

2026 Christmas events are coming in late November

More Christmas events arrive in late November. We add them here as soon as we confirm them.

The story of Christmas in Fairfield

Fairfield does not cut down a Christmas tree each year. It lights a living Norway spruce on the Town Hall Green, about 90 feet tall when Patch described it in 2016, and one of three trees the Daughters of the American Revolution gave the town in December 1918.

How Fairfield celebrates

The season begins on the Town Hall Green, where Fairfield Parks and Recreation runs the annual tree lighting. In past years choirs from the town's middle and high schools sang first, the First Selectman or First Selectwoman led the countdown, and Santa rolled in on a fire engine once the lights were on. In December 2024 the town added its first public menorah, lit alongside the tree. Downtown, the Chamber of Commerce brings Santa to the gazebo on Sherman Green, a visit that reached its 23rd year in 2025. A decorated-house fundraiser at the Burr Homestead dates to 1981, and the Fairfield Museum fills a gallery with model trains every winter.

Christmas last year in Fairfield

For November 30, 2025, the Chamber of Commerce announced Santa's 23rd annual arrival, with a hook-and-ladder truck carrying him down Reef Road to the Sherman Green gazebo, horse and wagon rides from Allegra Farms and a small holiday market. December 5 to 7 was set for the first Christmas at the Burr, a new festival from the volunteer charity Giving Fairfield that revived the spirit of the old Christmas Tree Festival and raised money for the Norma Pfriem Breast Center. The Fairfield Museum's Holiday Express Train Show ran through January 4, News 12 Connecticut reported hundreds of people at Chabad of Fairfield's menorah lighting on Sherman Green on December 14, and the Fire Department's Santa Express raised money for the Tommy Fund in mid-December.

Fun facts about Christmas in Fairfield

Patch called the Town Hall Green spruce the tallest living tree lit at Christmas in Connecticut. Parks and recreation staff estimated about 1,000 people at the December 2021 lighting, when Dwight Elementary School principal Mimi Maniscalco was nominated by a community member to switch on the lights. The first Fairfield Christmas Tree Festival in 1981 raised $12,500, and by 2011 the festival had raised more than $2.5 million for at least 90 local nonprofits.

Traditions today

  • Town Hall Green tree lighting: Parks and Recreation hosts the yearly lighting of the living Norway spruce on the Town Hall Green, with school choirs singing before the countdown.
  • Santa on a fire engine: Patch reports from 2016, 2019 and 2021 all have Santa arriving by Fairfield fire truck shortly after the tree is lit.
  • Tree and menorah lighting: Since December 2024, when the town displayed its first public menorah, the menorah has been lit alongside the town tree.
  • Santa's arrival on Sherman Green: The Fairfield Chamber of Commerce brings Santa down Reef Road on a hook-and-ladder truck to meet children in the gazebo, a visit in its 23rd year in 2025.
  • Holiday Express Train Show: Each winter the Fairfield Museum runs model trains through holiday villages with trains and track from the Housatonic Model Railroad Club and the Connecticut G-Scalers Club.
  • Christmas at the Burr: Launched in December 2025 at the Burr Mansion, this festival of decorated rooms carries on the idea of the Fairfield Christmas Tree Festival that began in 1981.

A fact for kids

Fairfield's Christmas tree is alive and still growing on the Town Hall Green, and it was already about 90 feet tall in 2016. After it lights up, Santa has arrived on a fire engine.

Questions about Christmas in Fairfield

How old is Fairfield's Christmas tree?

The tree on the Town Hall Green is a living Norway spruce. According to Patch, it was one of three trees donated to the town by the Daughters of the American Revolution in December 1918, which put it about 98 years in the ground by the 2016 lighting.

Where is Fairfield's tree lighting held and who runs it?

The ceremony takes place on the Town Hall Green, and Fairfield Parks and Recreation organizes it. In 2016 Patch reported that Local 1426 Fairfield Fire Fighters and Fairfield Fire Rescue sponsored the evening, with thanks going to the Public Works and Police departments as well.

How does Santa arrive at the Fairfield tree lighting?

By fire engine. Patch coverage from 2016, 2019 and 2021 describes Santa riding in on a Fairfield fire truck shortly after the tree is lit. In 2021 he brought Mrs. Claus, Rudolph, Frosty and several elves along with him.

Who gets to light the tree in Fairfield?

The town's top elected official has often led the countdown: First Selectman Mike Tetreau in 2016 and First Selectwoman Brenda Kupchick in 2019. In 2021 the honor went to Dwight Elementary School principal Mimi Maniscalco, who had been nominated by a community member.

When did Fairfield add a menorah to its holiday display?

In December 2024. News 12 Connecticut reported that the Fairfield Jewish Advocacy Coalition announced the first public menorah in the town's history, to be lit alongside the town Christmas tree that Saturday. The Fairfield Museum's 2026 calendar refers to the town's tree and menorah lighting ceremony.

How many people come to the Fairfield tree lighting?

Patch reported that parks and recreation staff estimated about 1,000 people on the Town Hall Green for the December 2021 lighting. That evening included singing by Fairfield middle school students, the Fairfield Warde High School Chorale and Fairfield Center Stage.

What is Santa's arrival on Sherman Green?

It is the Fairfield Chamber of Commerce's yearly Santa visit, in its 23rd year in 2025. Santa rides a hook-and-ladder fire truck down Reef Road, then meets children in the decorated gazebo on Sherman Green, where his elves hand each child a small plush holiday toy.

What was the Fairfield Christmas Tree Festival?

It was a fundraiser that began in 1981 after friends came up with the idea on a Fairfield beach. On the first weekend of December, designers decorated the rooms of the Burr Homestead, and handmade trees, wreaths and garlands were sold to benefit a local nonprofit.

What is Christmas at the Burr?

It is a festival run by the volunteer charity Giving Fairfield, first scheduled for December 5 to 7, 2025, at the Burr Mansion on Old Post Road. It revives the spirit of the earlier Christmas Tree Festival with decorated rooms, Santa visits, a gift boutique and a family pajama party.

What is the Holiday Express Train Show?

It is the Fairfield Museum's annual winter exhibit of model trains running through holiday villages. The Housatonic Model Railroad Club and the Connecticut G-Scalers Club supply trains and track, and News 12 reported in 2025 that club members are on hand to answer visitors' questions.

What is the Santa Express in Fairfield?

News 12 Connecticut describes the Santa Express as an annual Fairfield tradition run by the Fire Department together with Santa. In December 2025, children shared last-minute wishes with him, and proceeds went to the Tommy Fund, which raises money for children with cancer.

Sources

  1. Fairfield Town Hall Tree Lighting Details Announced, Patch
  2. Town Christmas Tree Lighting Friday In Fairfield, Patch
  3. Photos: Hundreds Turn Out For Fairfield Tree Lighting, Patch
  4. 'More light': Fairfield displays first public menorah in town history, News 12 Connecticut
  5. Santa Claus Visits Fairfield This Month, Patch
  6. Happy Anniversary to the Fairfield Christmas Tree Festival, Patch
  7. Christmas at the Burr, Patch
  8. 'Young people are just enraptured': Fairfield Museum's Holiday Express Train Show back for the holidays, News 12 Connecticut
  9. Santa Express in Fairfield brings holiday cheer and raises thousands for the Tommy Fund, News 12 Connecticut
  10. Fairfield marks the start of Hanukkah with holiday village, menorah lighting, News 12 Connecticut
  11. Holiday Express Train Show, Fairfield Museum and History Center

Keep 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.

Fairfield Christmas events for kids: questions parents ask

What is the best Christmas event for kids in Fairfield to start with?

Start with the Holiday Express Train Show at the Fairfield Museum on Beach Road. Its grand opening is Saturday, November 28, 2026, from 5:00 to 7:00 pm, right after the town's tree and menorah lighting ceremony, and the museum lists the model trains as running through January 3, 2027.

Where can kids meet Santa in Fairfield?

Santa visits the Fairfield Museum twice. He is at the Holiday Pop-Up Market on Saturday, November 14, 2026, from 10:00 am to 12:30 pm, and inside the Holiday Express Train Show on Saturday, December 5, with a members-only half hour at 9:30 am and a public session from 10:00 to 11:30 am.

Are there free Christmas events for kids in Fairfield?

Meeting Santa at the Holiday Pop-Up Market on November 14 is free for children 12 and under, while adults pay $5 at the door. At the train show, the museum lists members and children 5 and under as free, with $3 for older children and seniors and $5 for adults.

Is there a Christmas show for young children in Fairfield?

Yes. Fairfield Theatre Company stages The Christmas Express at The Warehouse at FTC from November 28 to December 29, 2026. It is a musical of about an hour made for preschool and elementary ages, with 16 performances and cabaret tables where families can bring their own picnic.

Which Fairfield Christmas events need tickets or sign-up?

The Christmas Express needs a ticket and a reserved seat for every guest, including infants on laps. The museum events are pay at the door: the pop-up market on November 14 takes cash or card, and the Santa visit on December 5 is included with museum admission. The 9:30 am Santa slot that day is for members only.

Why do trains come up so often at Christmas in Fairfield?

Two of the town's holiday events are built around them. The Fairfield Museum runs large and small model trains through winter villages with support from the Connecticut G-Scalers Club and the Housatonic Model Railroad Club, and The Christmas Express musical plays just steps from the Fairfield train station.

Are there Christmas train rides for kids near Fairfield?

Santa trains and holiday train rides have their own guide: Rally Takes the Train’s Connecticut Christmas train rides guide. This Fairfield guide covers Santa visits, story times, light shows and other events off the rails.

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 every listing on November 10, 2026. Hosts change details, so always confirm on the host’s page before you go.

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.

Kelsey Cecil
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