The Polar Bear Skate at the Bentway Park, just outside Old Fort York and under the Gardiner Expressway, is where you skate in your underwear, and the 2024 skate is already sold out. The event happens on Sunday, December 28, 2025 at 12 noon and asks for donations of warm winter clothing. Home Network and Flavour Network are providing complimentary rental skates along with free beverages and cookies (while supplies last). See photos of the 2024 skate on my post here.
From their website, "The Bentway’s boldest winter ritual returns on December 28 with the cheeky Polar Bear Skate! Brave Torontonians are invited to strip down to their skivvies and take a fearless lap around trail to bid farewell to 2025."
Round two is the polar dips happening on New Year's Day (Thursday, January 1, 2026). There is two swims happening - one at Sunnyside Beach and one at Woodbine Beach.
--------------------------Polar Bear Dip 2026----------------------------------------------------------------------
Yes it will be cold as the Polar Bear Dip "Dare to Dip" takes place at the famous lake side building known as the Sunnyside Bathing Pavilion. Taking place on New Year's Day at 12 noon, come earlier to register (opens at 10am), find a waiting spot and help raise money for Boost Child and Youth Advocacy Centre.
Their checklist is a great idea on the preparations you should make for running into the winter time Lake Ontario.
"Dip Day checklist:
To make your experience as enjoyable as possible, we recommend at least the following:
Proper Footwear – Stepping on something rocky or pointy isn’t fun in freezing cold water.
Wear full water sandles or water socks (best) or old running shoes (ok, just make sure they fit snugly).
DON’T WEAR FLIP FLOPS!
Lots of towels
A blanket to claim your patch of beach and to change on
Warm loose fitting clothes and footwear that are easy to put on in a hurry when you get out of the water (big loose fitting boots are amazing)
!!! Important !!! Bring a friend to mind your stuff and help you when you get out of the water.
If it’s a really cold day, your feet and fingers won’t work real well after the dip so you’ll probably need some help and since we don’t have change rooms,
someone to hold up a towel for you can be handy…"
--------------------------Record Breaker Cold Plunge 2026---------------------------------------------------------
Jack Org is back in Woodbine Beach for another polar event. It was previously known as Brainfreeze, now known as the Record Breaker World Record Cold Plunge. Also held on New Year's Day Thursday, January 1, 2026 but further east at Woodbine Beach from 1-2pm.
From their website, "Join us January 1st, 2026 at Woodbine Beach to plunge yourself into the chilly waters with like-minded individuals on the first day of the New Year. Get ready to dive into an invigorating experience that will leave you feeling refreshed, energized and ready to take on 2026 feeling more capable than ever.
Whether you're a seasoned cold plunging enthusiast or a first-timer, this event is open to all. Come join us in collaboration with Jack.org to raise funds towards youth mental health. Grab your swimsuit, towel, and a sense of adventure, and prepare to plunge into the cold waters together, as a community. Let's get uncomfortable for a cause."
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