Rally the corgi has sniffed out the Christmas events for kids in Winter Park for 2026, and they make one perfect weekend on Park Avenue. Winter on the Avenue lights the Central Park tree with Santa and Mrs. Claus on Friday evening, December 4, and the Ye Olde Hometown Christmas Parade marches down Park Avenue the next morning, 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 Florida Christmas events for kids guide.
What Rally found in Winter Park
- 2 Christmas events for kids in Winter Park, FL
- Both are free and both are on Park Avenue
- Winter on the Avenue: Friday, December 4, 5 to 9 pm, tree lighting and Santa
- Christmas Parade: Saturday, December 5, 9 am
- Every date checked on the Winter Park Chamber’s site on Nov 11
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All 2 events
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Rally’s Christmas research
Rally the corgi has 1 more Winter Park 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 Winter Park.
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Free Christmas events for kids in Winter Park
Tree lightingFree
Winter on the Avenue
- When: Friday, December 4, 2026, 5 to 9 pm
- Where: Central Park and Park Avenue, 150 W Morse Blvd, Winter Park, FL 32789 (opens in maps)
- Cost: Free
- Ages: All ages
Expand to see the parent tip
Winter on the Avenue is Winter Park’s kickoff to the holidays: Park Avenue closes to cars and turns into a pedestrian street party along Central Park on the first Friday evening of December.
The city tree in Central Park is lit with a countdown, Santa and Mrs. Claus come to visit, and carolers stroll the avenue, including the Belles and Beaux from Central Florida Vocal Arts. Shops and restaurants stay open, so it doubles as an easy family dinner out.
Parent tip: Arrive well before the tree lighting countdown, since the lawn fills fast. SunRail stops at the edge of Central Park if you would rather skip parking.
- Host
- Winter Park Chamber of Commerce with the City of Winter Park (opens in a new tab)
- Address
- Central Park and Park Avenue, 150 W Morse Blvd, Winter Park, FL 32789 (opens in maps)
- Confirmed
- On the host’s page, checked
New Winter Park events every week
Rally researches Christmas events in Winter Park daily and updates this page with new events. Enter your email to get a weekly update with new events in Winter Park.
Free. Unsubscribe anytime. Privacy policy (opens in a new tab)
Rally’s Christmas research
Rally the corgi has 1 more Winter Park 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 Winter Park.
- Exclusive access to free events Find the free Christmas events in Winter Park 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 Santa
- 1 Lights
- 1 Parades
- 2 Free
Enter your email to get new Christmas events in Winter Park every week.
ParadeFree
Winter Park 'Ye Olde Hometown' Christmas Parade
- When: Saturday, December 5, 2026, 9 to 10:30 am
- Where: Park Avenue, Downtown Winter Park, Park Ave from Cole Ave to Pennsylvania Ave, Winter Park, FL 32789 (opens in maps)
- Cost: Free to watch; pancake breakfast in Central Park is extra
- Ages: All ages
Expand to see the parent tip
The Winter Park Christmas Parade is the oldest continuous holiday parade in Central Florida, and it still has a hometown feel. More than 80 groups march down Park Avenue: bands, scout troops, police and fire, local leaders and, at the end, Santa Claus.
It is a morning parade, so little ones are fresh for it. Before and during the parade, Leadership Winter Park serves a pancake breakfast in Central Park that supports student scholarships and local nonprofits.
Parent tip: Grab pancakes in Central Park from 7 am, then claim a curb on Park Avenue before 9. The route runs south from Cole Avenue, so the north end gets the floats first.
- Host
- Winter Park Chamber of Commerce (opens in a new tab)
- Address
- Park Avenue, Downtown Winter Park, Park Ave from Cole Ave to Pennsylvania Ave, Winter Park, FL 32789 (opens in maps)
- Confirmed
- On the host’s page, checked
New Winter Park events every week
Rally researches Christmas events in Winter Park daily and updates this page with new events. Enter your email to get a weekly update with new events in Winter Park.
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 Florida Christmas train rides page.
See every event on a December calendar
Plan your December
When each Winter Park Christmas event for kids happens
Winter on the Avenue is Friday evening, December 4, and the Christmas Parade is the next morning, Saturday, December 5, at 9 am. Both use Park Avenue and Central Park, so it is one weekend trip.
- Winter on the AvenueWinter Park · Dec 4
- Winter Park 'Ye Olde Hometown' Christmas ParadeWinter Park · Dec 5
Looking further afield? Our Florida Christmas events for kids guide lists every confirmed event in the state, and we have city guides for Maitland, Orlando, Casselberry and Winter Garden. 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 Florida city.
Winter Park Christmas events for kids: questions parents ask
What are the best Christmas events for kids in Winter Park, FL this year?
Rally Takes the Train has confirmed 2 Christmas events for kids in Winter Park, Florida for 2026: Winter on the Avenue on Friday, December 4, and the Ye Olde Hometown Christmas Parade on Saturday, December 5. Both are free.
When is the Winter Park tree lighting in 2026?
The tree in Central Park is lit during Winter on the Avenue on Friday, December 4, 2026, which runs 5 to 9 pm on Park Avenue and in Central Park.
When is the Winter Park Christmas Parade?
Saturday, December 5, 2026, from 9 to 10:30 am on Park Avenue, from Cole Avenue south to Pennsylvania Avenue.
Where can kids meet Santa in Winter Park?
Santa and Mrs. Claus visit Winter on the Avenue on December 4, and Santa rides at the end of the Christmas Parade on December 5.
Is there a pancake breakfast before the parade?
Yes. Leadership Winter Park serves a pancake breakfast in Central Park before and during the parade on December 5.
Are there Christmas train rides for kids in Florida?
Yes. Santa trains and holiday train rides have their own guide: Rally Takes the Train’s Florida 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 Winter Park 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.