Rally the corgi has sniffed out the Christmas events for kids in Pickering for 2026, and all three are free. Santa leads the morning parade up Whites Road on Saturday, November 28, Winter Wonderland fills Millennium Square on the waterfront on December 5 and 12, and the holidays end with a New Year’s Eve Family Countdown on December 31. Every date comes from the City of Pickering festivals and events pages. For more across the country, see our Canada Christmas events for kids guide.
What Rally found in Pickering
- 3 free holiday events for kids in Pickering
- Santa Claus Parade: Saturday, November 28, 10 am, Whites Road
- Winter Wonderland: Saturdays, December 5 and 12, 11:30 am to 3 pm
- New Year’s Eve Family Countdown: December 31, 6:30 to 8:30 pm
- New for 2026: the parade moves to a temporary Whites Road route
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Free Christmas events for kids in Pickering
Morning paradeFree
Pickering Santa Claus Parade
- When: Saturday, November 28, 2026, 10 am start
- Where: Whites Road parade route, Pickering, Pickering, ON (opens in maps)
- Cost: Free
- Ages: All ages
Expand to see the parent tip
Pickering's Santa Claus Parade takes a temporary new route in 2026, forming at Dunbarton High School and heading north along Whites Road to the St. Mary's Catholic Secondary School parking lot.
It is a morning parade with a 10 am start, which suits little ones, and the City notes it is pet friendly as long as dogs stay leashed, though there are no public washrooms along the route.
Parent tip: Use the limited free parking at the nearby schools on Strouds Lane, Woodsmere Crescent or Parkside Drive, and remember spectators are not allowed on the railway bridge.
- Host
- City of Pickering Community Services (opens in a new tab)
- Address
- Whites Road parade route, Pickering, Pickering, ON (opens in maps)
- Confirmed
- On the host’s page, checked
New Pickering events every week
Rally researches Christmas events in Pickering daily and updates this page with new events. Enter your email to get a weekly update with new events in Pickering.
Free. Unsubscribe anytime. Privacy policy (opens in a new tab)
Rally’s Christmas research
Rally the corgi has 2 more Pickering 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 Pickering.
- Exclusive access to free events Find the free Christmas events in Pickering 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 Shows
- 1 Santa
- 1 Parades
Enter your email to get new Christmas events in Pickering every week.
Waterfront holiday festivalFree
Winter Wonderland
- When: Saturdays, December 5 and December 12, 2026, 11:30 am to 3 pm
- Where: Millennium Square, Pickering waterfront, Pickering, ON (opens in maps)
- Cost: Free admission
- Ages: All ages
Expand to see the parent tip
The City brings the holidays down to the waterfront at Millennium Square and Nautical Village on two Saturdays in December, with live ice carving, festive music and buskers, and roaming characters.
Kids can make s’mores, try arts and crafts and pose at photo stations while parents browse the holiday market, and the daytime hours make it an easy outing with toddlers.
Parent tip: Dress for the lake wind, and come right at 11:30 am to watch the ice carvers start on fresh blocks.
- Host
- City of Pickering Community Services (opens in a new tab)
- Address
- Millennium Square, Pickering waterfront, Pickering, ON (opens in maps)
- Confirmed
- On the host’s page, checked
New Pickering events every week
Rally researches Christmas events in Pickering daily and updates this page with new events. Enter your email to get a weekly update with new events in Pickering.
Free. Unsubscribe anytime. Privacy policy (opens in a new tab)
Family countdownFree
New Year's Eve Family Countdown
- When: Thursday, December 31, 2026, 6:30 to 8:30 pm
- Where: Chestnut Hill Developments Recreation Complex, Pickering, ON (opens in maps)
- Cost: Free skating and swimming
- Ages: All ages
Expand to see the parent tip
Pickering wraps up the holiday break with an early New Year's Eve party at the Chestnut Hill Developments Recreation Complex, with free skating and swimming for all ages.
The night ends with a balloon drop before a family countdown, all wrapped up by 8:30 pm so kids can celebrate without staying up until midnight.
Parent tip: Pack swimsuits and skates in the same bag and do one activity before the balloon drop, since the evening is only two hours long.
- Host
- City of Pickering Community Services (opens in a new tab)
- Address
- Chestnut Hill Developments Recreation Complex, Pickering, ON (opens in maps)
- Confirmed
- On the host’s page, checked
New Pickering events every week
Rally researches Christmas events in Pickering daily and updates this page with new events. Enter your email to get a weekly update with new events in Pickering.
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? Our Canada Christmas events for kids guide lists Santa trains and holiday rides across the country.
See every event on a December calendar
Plan your December
When each Pickering Christmas event for kids happens
Catch Santa at the morning parade on November 28, pick one Winter Wonderland Saturday on the waterfront, and save the family countdown for December 31.
- Pickering Santa Claus ParadePickering · Nov 28
- Winter WonderlandPickering · Dec 5 to Dec 12
- New Year's Eve Family CountdownPickering · Dec 31
Looking further afield? Our Canada Christmas events for kids guide lists every confirmed event in the country, and we have city guides for Whitby, Oshawa, Toronto and Mississauga. 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 Canada city.
Pickering Christmas events for kids: questions parents ask
What are the best Christmas events for kids in Pickering this year?
Rally Takes the Train has confirmed 3 free holiday events for kids in Pickering for 2026, all run by the City of Pickering: the Santa Claus Parade on November 28, Winter Wonderland on December 5 and 12, and the New Year’s Eve Family Countdown on December 31.
When is the Pickering Santa Claus Parade in 2026?
Saturday, November 28, 2026, starting at 10 am. It forms at Dunbarton High School and travels north on Whites Road to the St. Mary’s Catholic Secondary School parking lot.
Why did the Pickering parade route change?
City Centre development means Glenanna Road south of Highway 2 is unavailable for the parade to disband, so the City is using a temporary Whites Road route in 2026.
When is Winter Wonderland in Pickering?
Saturday, December 5 and Saturday, December 12, 2026, from 11:30 am to 3 pm at Millennium Square and Nautical Village on the waterfront. Admission is free.
Who do I contact about Pickering holiday events?
The City of Pickering events team: Isla McLaughlin, Event Coordinator, at imclaughlin@pickering.ca or 905-420-4660 ext. 1122. Community Services can also be reached at 905-420-4620.
Are there more Christmas events near Pickering?
Yes. Our Canada Christmas events for kids guide lists every confirmed event in the country, and the national search sorts events by distance from your town.
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 municipal or tourism calendar. We last checked Pickering on November 11, 2026. Rally is also contacting each organizer to confirm details like parking, washrooms 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.