Family Day weekend is your invitation to slow down, bundle up, and make memories that will be talked about long after the snow melts. In York Durham Headwaters, winter isn’t something to escape — it’s something to embrace. From snowy outdoor adventures to creative indoor escapes and special one-day celebrations, there’s no shortage of ways to turn this long weekend into something truly memorable for the whole family.
Whether you’re planning ahead for the full weekend or looking for something special to do on Family Day itself, here’s your guide to making the most of the season.
Things to Do All Family Day Weekend Long
These experiences run throughout the long weekend, giving you flexibility to mix, match, and build your perfect winter itinerary.
Hit the Slopes
Ski season is in full swing, and YDH is home to some of Ontario’s best family-friendly hills. Spend the day carving fresh tracks or warming up in the chalet at:
- Lakeridge Ski Resort (Uxbridge)
- Brimacombe (Clarington)
- Dagmar Ski Resort (Uxbridge)
- Hockley Valley Resort (Hockley)
- The ROC (Georgina)
- Uplands Golf & Ski Club (Thornhill)
Snow Tubing Fun
No lessons required — just pure joy. Race down the lanes at The ROC or Lakeridge Ski Resort, where laughter echoes louder than the wind.
Oshawa Generals vs. Peterborough Petes
There’s nothing like a hometown rivalry to bring the family together. Catch the Oshawa Generals facing off against the Peterborough Petes in Oshawa for a high-energy night of hockey excitement.
Ignite the Night at Terra Cotta Conservation Area
Step into a glowing winter forest during this magical nighttime experience. Rent snowshoes, cross-country skis, or kick sleds, or simply wander the illuminated trails beneath the stars.
Indoor Adventures for Cold Days
Warm up with these crowd-pleasing indoor experiences:
- Reptilia (Whitby & Vaughan) – up-close encounters with fascinating reptiles.
- GlowTown (Stouffville) – glowing mini putt, arcade games, and active fun.
- Volt Raceway (Bowmanville) – high-energy indoor entertainment for all ages with indoor go-carting, bowling, golfing, and more.
Island Lake Ice Fishing Derby
Cast a line at the Island Lake Ice Fishing Derby, with a special Youth Derby happening all weekend long in Orangeville — perfect for little anglers learning the ropes.
Feed the Chickadees at Lynde Shores Conservation Area
Bundle up and head to the Chickadee Trail at Lynde Shores Conservation Area in Whitby, where friendly birds may eat right from your hand — a simple moment that feels like pure winter magic.
Winter Adventure at Albion Hills
Try something new with fat biking, cross-country skiing, snowshoeing, or even winter disc golf at Albion Hills Conservation Area in Caledon.
Get Creative at Orangeville Pottery Parties Studio
Swap snow boots for aprons and spend an afternoon crafting something handmade to take home — a keepsake from your Family Day weekend.
Things to Do Specifically on Family Day – Monday Feb 16th
Looking for something extra special on the holiday itself? These one-day events are designed to bring families together in unforgettable ways.
Fair Havens Family Day Winter Event
A true winter wonderland experience in Beaverton featuring:
- Cross-country skiing
- Snow painting
- Shelter building
- Kick sledding
- Wagon rides
- Maple taffy in the snow
Plus warm drinks and a pancake breakfast or lunch to keep everyone fueled for fun.
Hockley Valley Resort Family Day Package
Turn Family Day into a full weekend getaway. This package includes:
- Overnight accommodations
- Breakfast
- Lift tickets for each family member
- A $50 resort voucher
- Kid-friendly activities running throughout the day and evening
Beauty and the Beast at City Playhouse Theatre
Experience the magic of a classic fairy tale brought to life on stage in Vaughan — perfect for families who love music, storytelling, and a little theatrical sparkle.
Ajax Winterfest
A community favourite with both indoor and outdoor activities, offering something for every age and energy level
Family Day Adventure at the McMichael Canadian Art Collection
Spend the day immersed in creativity with:
- Hands-on artmaking
- Storytelling
- Music and poetry
- Interactive experiences designed for families
Can’t make it on Monday?
Every third Sunday of the month is FREE Family Sunday at the McMichael, featuring themed activities, interactive tours, and special performances — making winter weekends even more magical.
Mansfield Outdoor Centre Family Day Winterfest
Visit Mansfield in Mulmur for their exciting winter festival:
- Cross-country ski lessons and groomed trails
- Snow sculpture contest
- Cookie decorating
- Corn hole
- Bonfire
- Crafts
- Hot chocolate relay (build a fire, boil your own water, and add hot cholate as fast as you can)
MoD Mini Olympics
Bring your family and friends for the MoD Mini Olympics!
In celebration of the 2026 winter Olympics join The Museum of Dufferin to play fun games, compete, and explore more of Dufferin’s Olympic history. From 10am- 3 pm, register online to reserve spot.
Make This Family Day One to Remember
Winter memories have a way of sticking with us — the rosy cheeks, the shared laughs, the moments spent together away from busy schedules. This Family Day weekend, let York Durham Headwaters be the backdrop for your next favourite family story.
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