Rally the corgi has sniffed out the best Christmas events for kids in Woodbury for 2026, and here is what he found: 3 family events. They are Make Gingerbread French Toast (December 2), CT Yuletide Carolers (December 5) and Ugly Sweater & Gingerbread Party (December 22). 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 Woodbury
- 3 Christmas events for kids in Woodbury
- Also on the list: 1 Christmas show
- Season: December 2 (Make Gingerbread French Toast) to December 22 (Ugly Sweater & Gingerbread Party)
- Every date checked on the host’s own site on Nov 10
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All 3 events
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Rally’s Christmas research
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- 1 Zoos and museums
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Ticketed and paid Christmas events for kids in Woodbury
Admission, tickets or a fee apply. Where a host has not posted a price yet, the listing says so.
Holiday event
Make Gingerbread French Toast
- When: Wednesday, December 2, 2026, 1:30 to 2:30 pm
- Where: Woodbury Public Library, Library Gallery Space, 269 Main St S, Woodbury, CT 06798 (opens in maps)
- Cost: No price listed on the organizer's page, registration required
- Ages: Teens
Expand to see the parent tip
Food Explorers leads this hands-on cooking session for teens in the library's Gallery Space. Each teen mixes a gingerbread-spiced egg wash, dips the bread and sees it cooked on a griddle until crisp, then eats it with whipped cream made from scratch.
The class runs on Wednesday, December 2, 2026, from 1:30 to 2:30 PM. Registration through the library's event page is required, and the group is small: the listing showed nine seats remaining. The page does not list a price.
Parent tip: Seats are counted in single digits, so register as soon as your teen says yes. The recipe is nut free but contains dairy and gluten, so it will not suit a teen who avoids either one.
- Host
- Woodbury Public Library (opens in a new tab)
- Address
- Woodbury Public Library, Library Gallery Space, 269 Main St S, Woodbury, CT 06798 (opens in maps)
- Confirmed
- On the host’s page, checked
New Woodbury events every week
Rally researches Christmas events in Woodbury daily and updates this page with new events. Enter your email to get a weekly update with new events in Woodbury.
Free. Unsubscribe anytime. Privacy policy (opens in a new tab)
Rally’s Christmas research
Rally the corgi has 2 more Woodbury events 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 Woodbury.
- Exclusive access to free events Find the free Christmas events in Woodbury 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
- 2 Breakfast and treats
- 1 Shows
- 1 Zoos and museums
Enter your email to get new Christmas events in Woodbury every week.
Holiday show
CT Yuletide Carolers
- When: Saturday, December 5, 2026, 2 to 3 pm
- Where: Woodbury Public Library, Main Library, 269 Main St S, Woodbury, CT 06798 (opens in maps)
- Cost: No price listed on the organizer's page
- Ages: All ages
Expand to see the parent tip
This hour of music is what the library calls its annual Christmas Festival event. The Connecticut Yuletide Carolers come dressed in traditional Victorian outfits and sing holiday harmonies in the Main Library, and holiday cookies are set out for the audience.
It takes place on Saturday, December 5, 2026, from 2:00 to 3:00 PM. The library lists it as a drop-in program for children, teens and adults, with no registration form and no price on the page.
Parent tip: Because it is drop-in, you can arrive partway through or slip out early if a little one runs out of patience before the hour is up. The Victorian costumes give small children something to look at while they listen, so find a spot where they can see the singers.
- Host
- Woodbury Public Library (opens in a new tab)
- Address
- Woodbury Public Library, Main Library, 269 Main St S, Woodbury, CT 06798 (opens in maps)
- Confirmed
- On the host’s page, checked
New Woodbury events every week
Rally researches Christmas events in Woodbury daily and updates this page with new events. Enter your email to get a weekly update with new events in Woodbury.
Free. Unsubscribe anytime. Privacy policy (opens in a new tab)
Holiday event
Ugly Sweater & Gingerbread Party
- When: Tuesday, December 22, 2026, 2:30 to 3:30 pm
- Where: Woodbury Public Library, Teen Department, 269 Main St S, Woodbury, CT 06798 (opens in maps)
- Cost: No price listed on the organizer's page
- Ages: Teens
Expand to see the parent tip
The library's Teen Department hosts an hour-long party for teens three days before Christmas. The title names its two ingredients, ugly holiday sweaters and gingerbread, and the listing leaves the rest of the plan unstated.
The party is on Tuesday, December 22, 2026, from 2:30 to 3:30 PM in the Teen Department. The page lists the audience as teens and shows no registration form and no price.
Parent tip: Have your teen pick out or decorate a sweater ahead of time, since that is half of the event's name. The listing has no description, so call the library first if you need to know about allergens in the gingerbread.
- Host
- Woodbury Public Library (opens in a new tab)
- Address
- Woodbury Public Library, Teen Department, 269 Main St S, Woodbury, CT 06798 (opens in maps)
- Confirmed
- On the host’s page, checked
New Woodbury events every week
Rally researches Christmas events in Woodbury daily and updates this page with new events. Enter your email to get a weekly update with new events in Woodbury.
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 Woodbury Christmas event for kids happens
The first is Make Gingerbread French Toast in Woodbury on December 2; the last runs to December 22. Each bar spans an event’s dates, not every hour in them, so check the host’s page for times.
- Make Gingerbread French ToastWoodbury · Dec 2
- CT Yuletide CarolersWoodbury · Dec 5
- Ugly Sweater & Gingerbread PartyWoodbury · Dec 22
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 Meriden, New Haven, Bridgeport and Fairfield, CT. 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 Amazon2026 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 Woodbury
Leroy Anderson, the composer of "Sleigh Ride," made his home in Woodbury from 1948 until his death in 1975. In the same Litchfield County town today, Christmas for families gathers at the public library, where carolers in Victorian dress sing at what the library calls its annual Christmas Festival event.
How Woodbury celebrates
Woodbury's listed holiday programs all come from the Woodbury Public Library. The library describes its Connecticut Yuletide Carolers afternoon on Saturday, December 5, 2026, as its annual Christmas Festival event, with singers in traditional Victorian attire and holiday cookies in the Main Library. Teens get two programs of their own: a Gingerbread French Toast class with Food Explorers on December 2 in the Library Gallery Space, and an Ugly Sweater and Gingerbread Party in the Teen Department on December 22. The library is also holding what it calls its first ever Holiday Decor Swap on Saturday, November 21, with drop-off during the week before.
Fun facts about Christmas in Woodbury
Woodbury was founded in 1673, when fifteen families, about fifty people, came from Stratford to a settlement known as Pomperaug Plantation. The name Woodbury means "dwelling place in the woods," and the settlement was first recognized as a town in 1674. The town center has a mile-long stretch of older buildings on both sides of the road, including a Masonic Temple from 1839 that sits on top of a high cliff and is lit by spotlights at night. The 2020 census counted 9,723 residents, and Woodbury is often called Connecticut's antiques capital.
Traditions today
- Christmas Festival at the library: The Woodbury Public Library calls its December caroling afternoon its annual Christmas Festival event, held in 2026 on December 5 in the Main Library.
- Victorian carolers: The Connecticut Yuletide Carolers perform in traditional Victorian attire while families listen over holiday cookies.
- Teen gingerbread afternoons: Teens have two gingerbread-themed programs at the library in 2026, a French toast cooking class on December 2 and an ugly sweater party on December 22.
- Holiday Decor Swap: The library's first ever Holiday Decor Swap on November 21 invites adults and teens to trade Christmas, Hanukkah, Kwanzaa, New Year's Eve and winter items in good condition.
- The historic town center: A mile-long stretch of older buildings, including churches dated 1785, 1816 and 1818, lines both sides of the road through the center of Woodbury.
A fact for kids
The man who wrote the song "Sleigh Ride" lived in Woodbury from 1948 to 1975. The town's name means "dwelling place in the woods."
Questions about Christmas in Woodbury
When was Woodbury, Connecticut founded?
Woodbury was founded in 1673. Early that year fifteen families, about fifty people, arrived from Stratford, and the settlers drew up an agreement called the Fundamental Articles. The settlement was first recognized as a town in 1674.
How did Woodbury get its name?
The name Woodbury means "dwelling place in the woods." Before the settlers chose it, the area they arrived in was known as Pomperaug Plantation, a name that survives in the Pomperaug River, which forms in Woodbury where the Nonnewaug and Weekeepeemee rivers meet.
Who were the first settlers of Woodbury?
Two groups came from Stratford. One was made up of religious dissidents led by the Reverend Zachariah Walker, Woodbury's first minister. The other was led by Deacon Samuel Sherman, who had approval from the general court to buy land for a new settlement.
What is Woodbury known for?
Woodbury is often called Connecticut's antiques capital. In the late twentieth century, antique shops moved into many of the historic houses in the town center, where a mile-long stretch of older buildings lines both sides of the road.
What is the building on the cliff in Woodbury?
It is the Masonic Temple, built in 1839. The clapboard Greek Revival building sits on top of a high cliff reached by a long flight of steps, can be seen from a distance and is lit by spotlights at night.
Which Christmas composer lived in Woodbury?
Leroy Anderson, who composed "Sleigh Ride" and many other works, lived in Woodbury from 1948 until his death in 1975. He is listed among the town's notable residents, and his widow Eleanor Anderson also lived in Woodbury.
What happens at Christmas in Woodbury for families?
The Woodbury Public Library holds its annual Christmas Festival event on Saturday, December 5, 2026, from 2:00 to 3:00 PM. The Connecticut Yuletide Carolers sing in Victorian attire in the Main Library, and visitors can drop in and have holiday cookies.
Where do Woodbury's Christmas events take place?
All of the confirmed 2026 programs are inside the Woodbury Public Library. The carolers sing in the Main Library, the Gingerbread French Toast class meets in the Library Gallery Space, and the Ugly Sweater and Gingerbread Party is in the Teen Department.
Who organizes the Christmas events in Woodbury?
The Woodbury Public Library organizes all four holiday listings we found for 2026. One of them, the Gingerbread French Toast class on December 2, is taught by an outside group called Food Explorers, and the caroling is performed by the Connecticut Yuletide Carolers.
Is anything free at Christmas in Woodbury?
The library's event pages do not list a price for any of the holiday programs, so check with the library to be sure. The December 5 caroling is drop-in with no registration, while the December 2 cooking class for teens requires sign-up.
Sources
- Woodbury, Connecticut, Wikipedia
- CT Yuletide Carolers, Woodbury Public Library
- Make Gingerbread French Toast, Woodbury Public Library
- Ugly Sweater & Gingerbread Party, Woodbury Public Library
- Holiday Decor Swap Drop-Off, Woodbury Public Library
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.
Woodbury Christmas events for kids: questions parents ask
What is the best Christmas event for kids in Woodbury to start with?
Start with the CT Yuletide Carolers at the Woodbury Public Library on Saturday, December 5, 2026, from 2:00 to 3:00 PM. It is the only listed program open to children of every age, the singers wear Victorian costumes, and holiday cookies are served while they perform.
Are there free Christmas events for kids in Woodbury?
The library's pages do not state a price for any of its holiday programs, so we cannot confirm them as free. The CT Yuletide Carolers on December 5, 2026 is a drop-in program with no registration form, which makes it the easiest one to simply walk into.
Where can kids meet Santa in Woodbury?
None of the Woodbury listings we confirmed for 2026 include a Santa visit. The closest thing to a classic Christmas outing is the library's annual Christmas Festival event on December 5, when the Connecticut Yuletide Carolers sing in the Main Library from 2:00 to 3:00 PM.
Is there a Christmas show or concert for families in Woodbury?
Yes. The Connecticut Yuletide Carolers perform at the Woodbury Public Library on Saturday, December 5, 2026, from 2:00 to 3:00 PM. They dress in traditional Victorian attire and sing in the Main Library, and the library sets out holiday cookies for people who drop in.
Which Woodbury holiday events need registration?
Make Gingerbread French Toast on Wednesday, December 2, 2026 requires registration, and the listing showed only nine seats remaining. The CT Yuletide Carolers on December 5 is drop-in, and the Ugly Sweater and Gingerbread Party on December 22 shows no registration form on its page.
What is there for teens in Woodbury at Christmas?
The library has two teen programs. Food Explorers teaches a Gingerbread French Toast class on December 2, 2026, from 1:30 to 2:30 PM in the Library Gallery Space, and the Teen Department holds an Ugly Sweater and Gingerbread Party on December 22 from 2:30 to 3:30 PM.
Are there Christmas train rides for kids near Woodbury?
Santa trains and holiday train rides have their own guide: Rally Takes the Train’s Connecticut Christmas train rides guide. This Woodbury 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.