Posted : November 20, 2025
Our blog is chock full of great ideas for fun things to see and do in York Durham and Headwaters. We are always adding new content and updating old posts, but sometimes you might stumble upon something from our vault. If this article has inspired you to hit the road, be sure to double-check that the featured stops in this post are still welcoming visitors.
As the leaves disappear and the temperature drops, the festive decorations appear and the Christmas music begins to play. However if you don’t celebrate, you may not know how to pass the time! Luckily there is plenty of fun to be had in York Durham Headwaters so you can enjoy all we have to offer. It’s guaranteed to make you feel like the main character in your own holiday movie!
Check Out a Winter Event
There are many events across YDH that celebrate the winter season. Check out one (or all!) of these great things to do!
There’s no better place to kickstart the season of wintery fun than at Canada’s Wonderland. From November 15 to January 3, 2026, Winterfest transforms the park into a magical holiday experience the whole family will adore. Enjoy ice skating on Snowflake Lake, take in one of their live shows, admire the millions of twinkling lights, indulge in deliciously festive eats and more. It’s certainly a one-of-a-kind holiday event you won’t forget!
Next, head to Pickering’s Esplanade Park for their Winter Nights, City Lights event on November 25th and 26th, 2023! Adorned with festive decor, you’ll enjoy numerous live performances, gorgeous art installations, a market with local vendors, tasty eats and plenty of fantastic photo opportunities. Esplanade Park will be the place to be so plan a family outing for some holiday fun!
Enjoying a night at the theatre is always a good idea. From November 30th to December 23rd, 2023, Theatre Orangeville is presenting “Cinderella… if the Shoe Fits”. Enjoy the boisterous live band as loveable characters bring this tale to life. The cast will have you in stitches with over-the-top shenanigans and plenty of humour. Audience participation is encouraged so cheer on the hero of the tale and yes, you can boo the villain too! Visit their website for more details.
Kick off the month of December with a visit to the Oshawa Museum for An Evening of Lamplight. On December 2nd from 6-8pm, guests will be greeted by staff members dressed in traditional Victorian clothes as Henry House is lit with stunning oil lamps. Attendees will be transported back to the 1800s so come and embrace the Victorian era with this unique annual event.
Last but certainly not least, add a splash of colour to your Sunday with a visit to the McMichael Canadian Art Collection in Kleinburg. Enjoy Family Sunday at the McMichael with special events planned all day long during the third Sunday of the month! From interactive tours to hands-on art workshops, there is plenty to do for the entire family. Plus, each Sunday has a different theme! Don’t miss the Winter Solstice Celebration at Free Family Sunday on December 21st, 2025!
Relax With a Staycation
Who says you need to travel far to make memories with friends and family? Plan one epic holiday adventure close to home here in York Durham Headwaters. There are so many unique places to stay overnight that you’ll adore.
Staying in a hotel is always a treat, especially for the little ones. Book a night at the Sheraton Parkway Toronto North Hotel & Suites and stay in their massive one-bedroom King Suite. The kids can cozy up in bed and watch a movie after splashing around in the indoor pool while the parents spoil themselves with room service delivered straight to your door. For those looking to enjoy a romantic getaway, splurge on the Presidental Suite at the Toronto Mariott Markham as you enjoy a glass of wine in front of the fireplace after a glorious swim in their elevated infinity pool.
If you’re looking to escape the city without having to travel too far, Mount Alverno is the epitome of rustic luxury. Nestled in the rolling hills of Caledon, this stunning resort is surrounded by 100 acres of natural beauty. You won’t believe you’re just 30 minutes from Brampton! Soak up the views along their picturesque hiking trails, lounge in their extravagant rooms and eat like a king (or queen) at their on-site restaurant, The Vista. Chef Denis crafts classic Canadian cuisine with a modern French twist to bring you fresh, seasonal dishes that are a treat for the taste buds.
Enjoy a Culinary Adventure in Markham
It’s no secret that Markham is home to a diverse population with a wide array of eats. However, it has become a culinary mecca for those looking for authentic Chinese cuisine. If you’re looking for some delicious comfort food to warm you up on those chilly winter days, look no further!
Start your day with some Dim Sum where you can sample several different Cantonese dishes. Not sure what to order? Try the Har Gow (shrimp dumplings), Siu Mai (pork dumplings) and Wotip (beef potsticker dumplings) to start, then see how adventurous you feel!
Hot Pot is another experience in Chinese cuisine that’s sort of like fondue but without the cheese! Enjoy a wide selection of sliced meats like beef, lamb and pork alongside seafood as well as numerous vegetables and dunk them into a steaming hot broth to cook as you please. It’s the perfect time to catch up with family and friends while you wait!
Another great option is “La Mian” or noodle pulling. You’ll be fascinated by this technique in Chinese cuisine as you watch these tasty noodles being made right before your eyes! The skill required is remarkable as you watch the noodle master stretch, pull and fold to ensure the perfect texture and thickness every time.
That’s not all Markham has to offer though! There are so many great spots for eats and treats so be sure to browse the City’s Global Food City culinary trail!
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