Toronto Holiday Guide
- Amanda Facciolo
- Dec 1, 2023
- 4 min read

The holidays are here and I'm about to make the most out of the winter season. Here are some activities that I'm hoping to check out this year.
Holiday Hills @ Stackt Market

Dates: November 17 - December 3
Location: 28 Bathurst St
Hours: Tuesday - Sunday
Gates: 9AM-11PM Shops: 12PM-8PM Food + Bev: Weekdays 4-11PM, Weekends 12-11PM Brewery: 12-11PM
Cost: FREE
What to expect:
This outdoor area has been designed entirely out of shipping containers. It's a marketplace mix of shops, microbrewery, top chefs, and killer city views.
Some of the fun activities include a:
Disco Mistletoe and Speakeasy Whiskey Bar
120 foot Tunnel of Lights with stunning city views
40 foot long Wish Wall for all of your holiday hopes
All-weather outdoor curling lanes with cozy warming huts to hang out in
20 foot tall holiday tree in the marketplace
Fizz & Fire patio with s'mores kits and a buzzing champagne bar
Taco Bar with seasonal offerings from Kong's Hot Tacos
Warm winter baos from Baobird
Free live music nights, Family Funday Sundays, vendor markets, and community-led events
One-of-a-kind holiday shopping pop-ups and a lot more!
There are so many things to see and do here that no matter when you go, it's going to be a lot of fun.
Second City's Holidazed & Confused

Dates: November 23 - December 31
Location: Theatre ’73 - 1 York Street
Hours: Thursday - Monday
Thursdays: 8:30pm
Fridays: 8:00pm
Saturdays: 8:00pm
Sundays: 7:30pm
Mondays: 8:00pm
Cost: $29 - $49
I LOVE comedy clubs, so if there is a holiday themed one, count me in! Let's grab our ugliest Christmas sweater and get ready for world-famous improv comedy stuffed with seasonal songs and sketches made to get you to LOLing all night long.
Evergreen Brickworks The Winter Market

Dates: December 10 + 17
Location: 550 Bayview Ave
Hours: 11AM - 5PM
Cost: This year is a “Pay What You Can Market”
What to expect:
I visit Brickworks almost every Saturday for their Farmers Market, but they have 2 Saturdays in December when they host a winter market. Ontario Artisan Market and Ontario Vintage Market will be there, offering items like vintage clothing, jewelry, candles, records, handmade cards and art. It’s the perfect place to pick up a present while supporting local vendors and giving someone a very special gift. They also will have a food court set up inside and food trucks outside serving up some incredible food and drinks.
If you have kids there are a lot of fun activities to do here. Most importantly, it's home to one of the cutest skating rinks in Toronto. It also has the Art Hive, where they provide recycled, upcycled, thrift store, natural, and donated materials for your creative art projects. Or check out the Weekend Nature Play where the kids will play snow at the Children’s Garden with sensory activities and arts and crafts.
Miacle Cocktail Bar

Dates: November 17 - December 31
Location: 875 Bloor St West
Hours:
Monday to Wednesday 6pm -12am
Thursday & Friday 6pm - 2am
Saturday 2pm - 2am
Sunday 2pm - 12am
19+ after 9 pm.
Cost: $5 cover fee for entry. A portion of proceeds goes to Nellie's Shelter, an organization providing shelter, education and advocacy for women and children in the GTA.
Miracle is a Christmas-themed pop-up cocktail bar that serves holiday cocktails in a festive holiday setting. It it a bit kitschy? Yes, but like the good kind of holiday cheer "kitschy"where you are being wrapped in a warm blanket. The cocktails have been dreamed up by the team at Civil Liberties - and with cocktail names like Holiday Spiked Chai, Elfing Around and Snowball Old Fashioned - you know they are going to be incredible.
The bar doesn't accept reservations so it may get busy on the evenings and weekend. But they do have a waitlist so check in there first before doing your winter shopping if you're in the area. Plus, $1 of every drink sold is donated to Nellie's Shelter. So you can feel good, while you sip.
Distillery District Winter Village

Dates: November 16 - Jauary 7
Location: 55 Mill Street
Hours:
Monday - Thursday & Sunday
Restaurants and retailers are open 10AM to 9PM
Outdoor shopping cabins and food vendor 12PM to 9PM
Friday & Saturday
Restaurants and retailers are open 10AM to 10PM
Outdoor shopping cabins and food vendors open 12PM to 10PM
Cost: FREE before 4PM. Tickets range from $15 - $45.
What to expect:
Be warned, on the weekends at night it can get very busy and waiting for a table at a restaurant can take some time so be mentally prepared.
They have the carolers, festive holiday décor and string lights and photo ops and St. Nick will be there to spread holiday cheer. Plus you have to check out the 56-foot-tall Christmas tree in Trinity Square (it's the tallest tree ever at The Distillery Winter Village!). This year some of the food vendors will include mini donuts, churros, tacos, empanadas, jerk chicken, pierogies, poutine, Pastel de Nata,, mini pancakes, raclette, crèpes and more!
Toronto Botaniacal Gardens

Dates: December 15 to 17
Location: 777 Lawrence Ave E
Hours: Friday: 2 to 8 p.m. | Saturday and Sunday: 10 a.m. to 4 p.m.
Cost: FREE
What to expect:
There will be over 100 local vendors that are showcasing their planet-friendly and botanically-themed products. From eco-friendly bath and beauty products to delicious homemade treats, holiday home decor and fesh seasonal greens for your home - there's something for everyone. Click here for the full vendor listing and program schedule.
Plus, there is a learning center that will be chatting all things holiday plants like Learn how to care for your new poinsettia, paperwhite, amaryllis and Christmas cactus and the best garden tools gifts. And a couple of days to warm up - including a 17′ human-size terrarium will be filled with tropical plants and a outdoor firepit to roast some marshmallows!
Canada's Wonderland Winterfest

Dates: November 17 - January 6
Location: 1 Canada's Wonderland Drive, Vaughan
Hours: Everyday from 5PM - 10PM
Cost: Starting from $29.99
What to expect:
I have never been, but my sister and her family has and it always looks like so much fun! Pictured here is my niece Naomi last year. Wonderland puts on an outdoor exerpeice like no other. There is no shortage of activities for the kids including:
Skating on Snow Flake Lake - right in front of the iconic mountain in the background.
Decorating cookies with Mrs. Claus herself.
Write a letter to Santa at the North Pole Postal Office
Seeing the reindeer from Santa's sleigh
Snacking on the festive funnel cake flavours like Candy Cane, Gingerbread and Classic Strawberry.
And there are still a lot of rides that will be open for you to ride too!
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