The Rutland area has 2 Christmas events for kids we could confirm for the 2026 season, from Downtown Rutland Tree Lighting in Rutland on November 27 to Holiday Stroll 2026 in Rutland, on December 12. 2 of them are free, and every listing links straight to the host. It is one stop on our guide to Christmas events for kids in Vermont, part of our guide for every state.
The short version
- 2 kids’ Christmas events confirmed in Rutland for 2026, in Rutland
- First: Downtown Rutland Tree Lighting, Rutland, November 27. Runs latest: Holiday Stroll 2026, Rutland, through December 12
- Free: Downtown Rutland Tree Lighting and Holiday Stroll 2026
- Checked on each host’s own page; each listing links straight to it
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Christmas events for kids in Rutland
2 confirmed events for kids in Rutland, soonest first.
Tree lightingFree
Downtown Rutland Tree Lighting
- When: Friday, November 27, 2026, 5:30 to 6:30 pm
- Where: Depot Park, Rutland
- Cost: Free
Details, tips and host
Downtown Rutland kicks off the holiday season the evening after Thanksgiving with a traditional tree lighting in Depot Park. Festive activities start at 5:30 pm, building up to Santa's arrival by fire truck at 6 pm, when he helps light the holiday tree.
Volunteers hand out hundreds of holiday light specs and candy canes during the event, which runs about an hour. The tree lighting is a free community event supported by the Downtown Rutland Partnership, Rutland City and the Rutland Recreation and Parks Department. The partnership posts updates on its Facebook event page, and questions can go to info@downtownrutland.com. The next day, November 28, is Small Business Saturday downtown, and the Holiday Stroll with a visit from Santa follows on December 12.
Parent tip: Arrive by 5:30 pm for the activities before Santa's 6 pm fire truck arrival. Dress warmly for an outdoor evening.
- Host
- Downtown Rutland Partnership (opens in a new tab)
- Address
- Depot Park, Evelyn Street and Merchants Row, Rutland, VT 05701
- Confirmed
- On the host’s page, checked
Santa visitFree
Holiday Stroll 2026
- When: Saturday, December 12, 2026, 10 am to 4 pm
- Where: Downtown Rutland historic district, Rutland
- Cost: Free to attend
- Ages: Family friendly
Details, tips and host
The Downtown Rutland Partnership's Holiday Stroll fills the historic downtown district with a day of holiday cheer. Local shops offer sales, specials and promotions, and the organizers promise family friendly fun throughout the day, including a special visit from Santa.
The stroll runs from 10 am to 4 pm on Saturday, December 12. When this listing was checked, the partnership said more details were coming, including Santa's location and timing and the list of participating merchants, so check the event page or its Facebook event before you go. The event is free to attend and is supported by sponsors and community partners. Families who missed the November 27 tree lighting in Depot Park can still catch the downtown decorations and see Santa on this day. Questions can be sent to info@downtownrutland.com.
Parent tip: Check the event page close to the date for Santa's exact time and spot, which had not been posted yet.
- Host
- Downtown Rutland Partnership (opens in a new tab)
- Address
- Downtown Rutland historic district, Merchants Row, Rutland, VT 05701
- Confirmed
- On the host’s page, checked
Look inside the book
Story time with Santa in Rutland? Bring Rally home.
Rally Takes the Train is a five-minute rhyming picture book about a corgi’s first train ride, hand-painted in real watercolor. It makes a cozy bedtime story after a big day with Santa. Turn a few pages here.
Rally Takes the Train
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Every event above was confirmed on the host’s own page, with the date, time, cost and the small things parents ask about (sign-ups, ages, what is included). Looking for a Santa train instead? Those are on our Vermont Christmas train rides page.
Rutland Christmas events for kids at a glance
- Kids’ Christmas events
- 2 confirmed for 2026
- Cities
- Rutland
- Season
- November 27 to December 12, 2026
- Free events
- 2
- Kinds of events
- tree lighting and Santa visit
- Last checked
See every event on a December calendar
Plan your December
When each Rutland Christmas event for kids happens
The first is Downtown Rutland Tree Lighting in Rutland on November 27; the last runs to December 12. Each bar spans an event’s dates, not every hour in them, so check the host’s page for times.
- Downtown Rutland Tree LightingRutland · Nov 27
- Holiday Stroll 2026Rutland · Dec 12
Looking further afield? Our Vermont Christmas events for kids guide lists every confirmed event in the state, and we have city guides for Burlington, VT and Montpelier. 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: unlock the list and we'll email you as soon as we confirm them.
The story of Christmas in Rutland
In Rutland, Santa arrives by fire truck. The tree lighting in Depot Park goes back to the 1930s, and in the 1950s and 1960s a lit Santa, sleigh and reindeer stretched across Merchants Row downtown.
How Rutland celebrates
The Depot Park tree lighting dates to the 1930s and continues today. Santa often flipped the switch, and a 1943 photo shows him climbing down a ladder from the Mead Building, across from the park. In the 1950s and 1960s lighted garlands hung across Merchants Row, Center Street and West Street, with large multicolored bulbs. Shop windows were decorated, and families came downtown at night to look. Toy shopping happened at the Economy, Woolworth's, Kresge's, Fishman's and a seasonal store called Toy Town.
Christmas last year in Rutland
The downtown tree lighting on Friday, November 28, 2025, was a free evening at Depot Park that started at 6 p.m. Santa arrived by fire truck at 6:30 to light the tree, with hot cocoa from Mission City Church, cookies and milk from The Pines, and free light specs and candy canes. Families then walked downtown to see decorated shop windows. A Holiday Window Contest gave a People's Choice Award to Triumph Barre, Yoga and Pilates Studio. The Chaffee Art Center gingerbread reception was held on December 6.
Fun facts about Christmas in Rutland
In the 1950s a lit Santa, sleigh and reindeer stretched across Merchants Row, and a newspaper photographer captured it at night as snow fell. Toy Town on Evelyn Street sold only toys and opened just for the season. Children spent their allowance on gifts for their mothers, like perfume and bubble bath from Woolworth's. Santa also arrives by fire truck rather than sleigh at the downtown tree lighting, and the gingerbread creations stay on view until early January.
Trains and Christmas near Rutland
The park that holds Rutland's tree lighting is called Depot Park, a hint of the city's railroad past. For train time, the Rutland Railway Museum in Center Rutland is a small, friendly museum in the old depot with N scale and HO scale layouts. The Green Mountain Railroad runs its Green Mountain Flyer between Bellows Falls and Chester Depot, and the working Bellows Falls Train Station has a model train village and is served by Amtrak's Vermonter.
- Rutland Railway Museum: A small museum inside the old Center Rutland depot with model train layouts and members happy to talk trains.
- Green Mountain Railroad: A Vermont shortline whose Green Mountain Flyer runs between Bellows Falls and Chester Depot.
- Bellows Falls Train Station: A working depot from about 1926 with a model train village, served by Amtrak's Vermonter.
Traditions today
- Depot Park tree lighting: A free evening in late November when Santa arrives by fire truck to light the downtown tree, a tradition from the 1930s.
- Holiday Window Contest: Downtown shops and restaurants compete with festive windows, judged by three guest judges and a public vote.
- Walking downtown after the lighting: Families stroll through downtown to see decorated shop windows once the tree is lit.
- Chaffee Art Center gingerbread contest: People of all ages show gingerbread creations, and visitors vote for their favorites.
- Light specs and candy canes: Volunteers hand out free holiday light specs and candy canes at the tree lighting.
A fact for kids
In Rutland, Santa arrives at the tree lighting on a fire truck instead of a sleigh! In the 1940s he even climbed down a ladder from a building across from the park.
Questions about Christmas in Rutland
How old is the Rutland tree lighting?
The Depot Park tree lighting dates to the 1930s and continues today, so it is nearly a century old. A 1943 photo shows Santa climbing down a ladder from the Mead Building across from the park to flip the switch. Today Santa arrives by fire truck.
Where is the Rutland Christmas tree lighting?
It is held in Depot Park in downtown Rutland. The 2025 event on Friday, November 28, was free and started at 6 p.m., with Santa arriving by fire truck at 6:30. For this season's confirmed date and time, see our Rutland Christmas events guide on this page.
Who lights the tree in Rutland?
Santa does. In the past he often flipped the switch, and today he arrives by fire truck at Depot Park to help light the tree. Kids can wave to him as he arrives, and volunteers hand out candy canes and light specs.
What happens after the Rutland tree lighting?
After the lighting, families walk through downtown to see decorated shop windows. In 2025 there was also hot cocoa from Mission City Church, cookies and milk from The Pines at Rutland Center for Nursing and Rehabilitation, and free holiday light specs and candy canes.
What did downtown Rutland look like at Christmas in the 1950s?
Lighted garlands hung across Merchants Row, Center Street and West Street, with large multicolored bulbs rather than small white lights. Shop windows were decorated, and families visited downtown at night. A lit Santa, sleigh and reindeer stretched across Merchants Row, and a newspaper photographer captured it as snow fell.
Where did Rutland kids shop for toys long ago?
Rutland kids shopped for toys at the Economy, Woolworth's, Kresge's and Fishman's, which all had toy departments in the 1950s and 1960s. Toy Town on Evelyn Street sold only toys and was open seasonally, and Wilson Sports on Center Street also stocked toys at Christmas time.
What was Toy Town in Rutland?
Toy Town was a seasonal store on Evelyn Street in Rutland that sold only toys. It operated in the 1950s and 1960s, when families also bought toys at Woolworth's, Kresge's and Fishman's. It is remembered by locals as part of a downtown Christmas that families visited at night.
What gifts did children buy in Rutland long ago?
Children spent their allowance on gifts for their mothers, such as perfume and bubble bath from Woolworth's. One Rutland resident remembered her mother buying an annual box of unscented soap for her teacher, a nun. These memories come from a local column recalling Rutland Christmases in the 1950s and 1960s.
What is the Rutland Holiday Window Contest?
It is an annual contest in which Downtown Rutland shops and restaurants compete with festive window displays. Three guest judges choose favorites in several holiday categories, and the public votes for the People's Choice Award. In 2025 the People's Choice Award went to Triumph Barre, Yoga and Pilates Studio.
What was Little's Lodge and Gift Shop in Rutland?
Little's Lodge and Gift Shop, run by Thelma Little at Center and Nickwackett Streets, was a yearly Christmas stop for one Rutland family, according to a local column about Christmases long ago. Another downtown store, Wilson Clothing Store, had a curved interior with entrances on both Merchants Row and Center Street.
What is the gingerbread contest in Rutland?
It is an annual contest at the Chaffee Art Center, 16 South Main Street, where people of all ages show their gingerbread creations and visitors vote for favorites. In 2025 the theme was heART-ful, the reception was held December 6, and displays stayed up until January 3, 2026.
Does Santa come to Rutland by sleigh?
Not for the tree lighting. Santa arrives by fire truck at Depot Park, and photos from the 2023 lighting show him on one. In the 1950s, though, a lit Santa, sleigh and reindeer display stretched across Merchants Row downtown, so kids could still see a sleigh.
How can I explain the tree lighting to my kids?
Tell them the whole town gathers in Depot Park on a cold November night, Santa rides in on a fire truck, and everyone counts down as the tree turns on. Then they get hot cocoa, candy canes and a walk downtown to look at the shop windows.
What are holiday light specs?
Holiday light specs are free glasses that volunteers hand out at the Rutland tree lighting, along with candy canes. They are a small keepsake for kids, who can look through them at the tree lights and decorated shop windows downtown.
Where can kids see Christmas lights in Rutland?
The Depot Park tree is lit at the start of the season, and downtown shop windows are decorated for the Holiday Window Contest. In the 1950s, garlands lit Merchants Row, Center Street and West Street. Our Rutland Christmas events guide on this page lists this season's confirmed dates.
Is there a Christmas parade in Rutland?
We did not find a Rutland Christmas parade in the sources we checked. The best known holiday tradition is the Depot Park tree lighting, where Santa arrives by fire truck. For this season's confirmed events, see our Rutland Christmas events guide on this page.
Is there a Christmas market in Rutland?
We did not confirm a Christmas market in our sources, but Rutland has other holiday traditions, including the Holiday Window Contest and a gingerbread contest at the Chaffee Art Center. Our Rutland Christmas events guide on this page lists this season's confirmed events and dates.
Where can kids see trains near Rutland?
The Rutland Railway Museum in Center Rutland is a small museum inside the old depot, with N scale and HO scale layouts, and it is open Saturdays from 11 a.m. to 3 p.m. The Bellows Falls Train Station also has a model train village. Check hours before you go.
Can kids ride a train in Vermont?
Yes. The Green Mountain Railroad's Green Mountain Flyer runs between Bellows Falls and Chester Depot, a trip of a little over two hours. Rides run spring through fall, so they are not a winter outing. Book through Vermont Rail System Passenger Services, and check the schedule for the current year.
What makes Christmas in Rutland different from other cities?
Rutland's holiday centers on Depot Park, where a tree lighting from the 1930s still draws families and Santa arrives by fire truck. Older residents remember a downtown glowing with garlands and a Santa sleigh over Merchants Row, and today shop windows compete in a friendly contest.
Sources
- Remembering Christmas from yesteryear, The Mountain Times
- Downtown Rutland Tree Lighting, Downtown Rutland
- Tree Lighting, Downtown Rutland, 11/28/2025, Rutland Region Chamber of Commerce
- Scenes from Downtown Rutland's holiday tree lighting, Downtown Rutland
- Holiday Window Contest, Downtown Rutland
- Annual Gingerbread Showcase in Rutland, Happy Vermont
- Rutland Railway Museum, Rally Takes the Train
- Green Mountain Railroad, Rally Takes the Train
- Bellows Falls Train Station, Rally Takes the Train
Rutland Christmas events for kids: questions parents ask
What are the best Christmas events for kids in Rutland this year?
We confirmed 2 for the 2026 season, and 2 of them are free. Good places to start: Holiday Stroll (Dec 12) and Downtown Rutland Tree Lighting (Nov 27). Every event on this page has the times, the cost and a link to the host.
Are there free Christmas events for kids in Rutland?
Yes, every event on this page is free. Some free events still need a reservation, so check the listing before you go.
Where can kids meet Santa in Rutland?
2 events here include a visit with Santa. Bring your own camera; most visits allow photos.
Are there Christmas train rides for kids in Rutland?
Yes, but they have their own guide. Santa trains and holiday train rides are listed in our Rutland Christmas train rides guide, so this page sticks to story times, Santa visits 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 4, 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.