TR Guide to Fun + Festive Holiday Events in Toronto/GTA
đź•’ 10 min read
Holiday season is in full swing this year, with a host of fun and festive events to get in on. Discover local markets, pop-up bars, activations and immersive experiences filled with an array of celebratory food, drinks and good cheer.
Featuring free and ticketed holiday-themed food and drink events happening in Toronto and the GTA in one convenient place, this guide will be updated throughout the season, so bookmark this page and check back often to discover what’s new!
CANADA’S WONDERLAND WINTERFEST
November 13 - December 31, 2021
Holiday fare includes mains, desserts and snacks from a host of vendors. Winter warm-ups of mulled cider and gourmet hot chocolate keep you warm all night long.
Canada’s Wonderland - 1 Canada’s Wonderland Dr., Vaughan
PAPI'S MISTLETOES AND MARGARITAS
November 17, 2021 – January 2, 2022
A Christmas pop-up featuring festive cocktails and holiday vibes. Ugly Christmas sweaters welcome.
Papi Chulo’s - 121 Ossington Ave. Toronto
THE DISTILLERY WINTER VILLAGE
November 18 – December 31, 2021
This year’s festivities include eight new vendors in cozy cabins offering seasonal items and 12 food cabins to explore, in addition to the Distillery District’s 75+ year-round local merchants, restaurants and extended patios.
Distillery District - 9 Trinity St., Toronto
WESTON WINTERFEST
November 19-21, 2021
Enjoy a holiday market, installations, talent show, musical pop-ups, ice sculptures and winter treats.
Artscape Weston Common - 34 John St., Toronto
MARKHAM HOLIDAY MARKET
November 19-21, 2021
Shop holiday gifts, décor, unique artisan gifts, gourmet food, meet Santa, and more.
Markham Fairgrounds - 10801 McCowan Rd., Markham
TORONTO ZOO HOLIDAY MARKETPLACE
November 19 – December 23, 2021
Visit the Zoo’s front courtyard and enjoy amazing producers, processors, and artisans from the community. Shop local while enjoying holiday-inspired food and drink, festive décor.
Toronto Zoo - 2000 Meadowvale Rd., Toronto
BAR NEON + BLOORDALE WINTER MARKET
November 21, 2021 -January 2, 2022
Featuring goods from local shops and artists from the Bloordale Community.
Every Friday and Saturday night a small donation is suggested for entrance to the market as either a non-perishable food item, or small monetary donation.
Bar Neon - 1226 Bloor St. W., Toronto
THE THIRSTY ELF
November 19 - December 18, 2021
Fairmont Royal York’s annual holiday pop-up and kitschy bar event.
Fairmont Royal York – 100 Front St. W., Avenues Level, Toronto
CHRISTMAS AT GIGGLEWATER
November 23 – December 26, 2021
A holiday pop-up filled with festive food and drinks, gift-wrapped tables, and holiday décor for days.
Project Gigglewater - 1369 Dundas St. W., Toronto
HOLIDAY HILLS
November 23 - December 31, 2021
Stackt’s outdoor holiday festival features three weekend vendor markets and 26 resident stores for holiday shopping, live music showcases, local art, holiday-themed workshops + DIYs, drag + comedy shows, and unique dining. It also marks the return of Crokicurl, a hybrid game of crokinole and curling played on a massive outdoor rink, as well as stackt’s first-ever rooftop patio, GoldInn.
Stackt Market – 28 Bathurst St., Toronto
POLAR WINTER FESTIVAL
November 25 - December 26, 2021
Enjoy the immersive, magical walk-through experience, then head for a seat by the fire and enjoy holiday cocktails at the X Lounge pop-up.
Bandshell Park, Exhibition Grounds - 100 Prince Edward Island Cres., Toronto
HOLIDAY FAIR IN THE SQUARE
November 26 – December 30, 2021
Take part in the walk-through Nights of Lights experience, shop for unique holiday gifts at the Artisan Marketplace, visit Santa, enjoy the winter carnival, grab drinks at Polar Point Bar.
Assembly Park - 80 Interchange Way, Vaughan
MIRACLE ON BLOOR ST.
November 25-December 26, 2021
A Christmas-themed pop-up cocktail bar that serves holiday cocktails in a festive setting, with kitschy holiday décor, professionally-developed cocktails and the nostalgic energy of the best office party you’ve ever been to.
$1 of every drink sold is donated to Nellie's Shelter, an organization providing shelter, education and advocacy for women and children in the GTA.
875 Bloor St. W., Toronto
PASKO SA KULTURA FESTIVAL
November 27, 2021
KAPISANAN presents “Pasko sa KULTURA”, hybridizing the popular “winter market” with Pasko (Filipino for Christmas). Held outdoors in partnership with Street Eats Market, Pasko sa KULTURA will feature live performances, an art installation and artisan market.
Scarborough Town Centre – 520 Progress Ave., Scarborough
STREETSVILLE CHRISTMAS IN THE VILLAGE
November 27- 28, 2021
Get into the holiday spirit at the Christmas Market, a visit with Santa, live entertainment, activities and more.
Streetsville Village Square - 213 Queen S.t S., Mississauga
DECK THE PALMS AT THE DIVE SHOP
December 1-31, 2021
The holidays are in full swing at Leslieville’s surf-inspired local with festive cocktails, decor and eats.
The Dive Shop - 1036 Gerrard St. E., Toronto
LITTLE SISTER JAVA JINGLE HOLIDAY HANGOUT
December 1, 2021 - January 1, 2022
LS Portland’s Balinese-inspired bar and dining room upstairs has been transformed into a tropical holiday-themed bar with festive cocktails and Dutch-Indonesian fare.
Little Sister Portland - 102 Portland St., Toronto
SWEATERS N' SNOWFLAKES
December 3-26, 2021
​Family friendly outdoor partially heated, wood fired food & wine bar. The holiday pop-up forest experience. includes, a wood fire BBQ pit and wood fire oven offering holiday inspired pizzas, wok fried noodles, desserts, and soups served in a festive slipper, glove or gift bag. The pop-up also offers many vegetarian options, mulled wine, spiked hot chocolate, apple cider, and holiday inspired cocktails. Special features include an Ugly Sweater Beer & Food Festival on December 18.
621 Richmond St. W., Toronto
HOLIDAY STREET MARKET
Dec. 3-5, 10-12, 17-19, 21-24, 2021
In addition to a walk-in tree, Artisan Village, rides and entertainment, discover food trucks, fire pit lounge, sugar shack, hot cocoa bar, mulled wine and 200 ft. long table.
Scarborough Town Centre – 520 Progress Ave., Scarborough
WYCHWOOD BARNS COMMUNITY ASSOCIATION HOLIDAY MARKET
December 5, 2021
Shop 40+ vendors, enjoy live music, coffee/hot chocolate, and crafts for the kids. It’s a real family event.
Order a WBCA Holiday Box: 13 special treats in one: $100 with proceeds to the WBCA. Order BEFORE Dec 3 from wbcaholidaybox@gmail.com and pick up at the market.
Wychwood Barns - 76 Wychwood Ave., Toronto
GRAPE CRUSH MINI HOLIDAY MARKET
December 5, 12, 19, 2021
Sip, savour and shop Sunday afternoons. Enjoy local artisans and creators, wine makers, wine agents, DJs and tarot readings. Complimentary wine and cheese tasting,
Grape Crush Wine Bar - 1166 Dundas St. W., Toronto
THE MISSISSAUGA FESTIVAL OF TREES
December 9-19, 2021
The festival celebrates the joy of the winter season, showcasing displays of seasonal lights, contemporary tree and woodpile art installations, artisan and culinary markets, entertainment, public workshops and a Family PJ Party at the historic Small Arms Inspection Building.
Small Arms Inspection Building - 1352 Lakeshore Rd. E., Mississauga
10TH ANNUAL RIVERSIDE ANTLER BREAKFAST (Virtual)
December 11, 2021
The Riverside Antler Breakfast is raising funds in support of the year-round operation of the local Rivertowne Breakfast Program.
Ways to support: General Admission Ticket, Brunch Box Ticket (option available until December 8, 6pm. Delivery will be December 10), Donation Ticket, Become a Sponsor or Donate to Live Auction.
The Rivertowne Breakfast Program was founded by Joan King and is championed by Rivertowne Safety 1st, a resident collective comprised of Toronto Community Housing women leaders dedicated to making a positive impact in their community. The Breakfast Program runs every Friday, year round, to provide about 100 children, seniors, and people with different abilities - including primarily BIPOC - in the local community with a free, warm breakfast. It also aims to bring people in the community together regardless of their family income level, and give them something to look forward to while building a sense of community.
CHAVETA COFFEE CHRISTMAS MARKET
December 11 + 18, 2021
Get into the holiday spirit at this Christmas market in Seaton Village featuring local vendors Clairette Wines, Raj's Saus, and Crafts in the City.
Chaveta Coffee - 994 Bathurst St., Toronto
TRANZAC HOLIDAY GIFT FAIR
December 11, 12, 18 + 19
TRANZAC Holiday Gift Fair is back this year featuring local vendors selling one of a kind handmade gifts.
Tranzac Club - 292 Brunswick Ave., Toronto
NIGHT MARKET TORONTO’S MISSISSAUGA FROST BITES
December 17-19, 2021
Mississauga's Frost Bites Outdoor Holiday Festival boasts delicious winter eats, sparkling winter forest, a giant mailbox for letters to Santa, and holiday vibes all around!
Square One - 100 City Centre Dr., Mississauga
EVERGREEN’S HOLIDAY MARKET
December 17-22, 2021
Shop local craft goods from over 40 artisan and vintage vendors in a a reimagined historic brick factory, skate on the picturesque outdoor skating rink, enjoy live music and end your stay with tasty and toasty eats and drinks.
TD Future Cities Centre, Evergreen Brick Works - 550 Bayview Ave., Toronto
LESLIEVILLE CHRISTMAS POP-UP MARKET
December 18-19, 2021
Eastside Events presents 8th Annual Leslieville Christmas Pop-up Market.
Enjoy a weekend of holiday shopping in a beautiful 10,000 sq. ft. historic indoor space. This is the only time the public can see this venue.
Featuring 30-40 curated vendors, Santa giving away candy, complimentary Hot Chocolate Deluxe Bar, holiday music. Enter to win a Christmas Morning Prize Pack. Enter your dog into Best Dog Holiday Costume Competition for prizes.
This event supports Second Harvest : Give what you can $/Non-perishable foods.
20 Wagstaff Dr., Toronto
Note: Event dates, prices and other information subject to change.
Know of a food/drink holiday event in the GTA? Get in touch.
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