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The Best Holiday Happenings in Toronto

Christine Peddie

Written By

Christine Peddie

The Best Holiday Happenings in Toronto

The best holiday happenings in Toronto will have you feeling as sprightly as an elf, all season long. Offering festive food and drinks that feed your need for luxury, kitsch, or both, these pop-ups and events should be mandatory on any holiday schedule.

Get in the holiday spirit today with the best holiday happenings in Toronto.

Gay Lea - Share Joy Pop-Up

Free fun for the whole family (even furry, four-legged members), the Share Joy by Gay Lea holiday pop-up will be taking over a space at 410 Front Street, at The Well, from November 30th to December 31st. Between the immersive activations, larger-than-life installations, hot cocoa, cookies and pup-cups, this one is more then likely to spark some serious holiday joy.

Gay Lea - Share Joy Pop-Up

Free fun for the whole family (even furry, four-legged members), the Share Joy by Gay Lea holiday pop-up will be taking over a space at 410 Front Street, at The Well, from November 30th to December 31st. Between the immersive activations, larger-than-life installations, hot cocoa, cookies and pup-cups, this one is more then likely to spark some serious holiday joy.

W Toronto

With a number of holiday-themed offerings, you can pick and choose how you fill up on festive cheer at W Toronto. If your idea of merriment includes chocolate yule logs, candy cane lipsticks and chilled prosecco, you'll definitely want to carve out time for a little Holiday High Beau-Tea. To reserve, visit Opentable.com.

W Toronto

With a number of holiday-themed offerings, you can pick and choose how you fill up on festive cheer at W Toronto. If your idea of merriment includes chocolate yule logs, candy cane lipsticks and chilled prosecco, you'll definitely want to carve out time for a little Holiday High Beau-Tea. To reserve, visit Opentable.com.

The Distillery Winter Village

True, the tree is splendid, the cobblestones shimmer, and the shops peddle a wealth of holiday-themed knickknacks. But it's the food that keeps us going back to the Distillery Winter Village, year after year. From festive poutine and dreamy decorated cookies to cotton candy and hot chocolate that could make Santa weep tears of joy, there's enough treats here to fuel hours of holiday strolling.

The Distillery Winter Village

True, the tree is splendid, the cobblestones shimmer, and the shops peddle a wealth of holiday-themed knickknacks. But it's the food that keeps us going back to the Distillery Winter Village, year after year. From festive poutine and dreamy decorated cookies to cotton candy and hot chocolate that could make Santa weep tears of joy, there's enough treats here to fuel hours of holiday strolling.

TD Union Winter

Not a fan of the cold? New this year, TD Union Winter invites visitors to strap on their roller skates for some free (indoor!) fun. Between December 1st and February 4th, visitors to Union Station can take part in classes, DJ skate nights, performances, holiday shopping, and plenty of festive snacks and sips.

TD Union Winter

Not a fan of the cold? New this year, TD Union Winter invites visitors to strap on their roller skates for some free (indoor!) fun. Between December 1st and February 4th, visitors to Union Station can take part in classes, DJ skate nights, performances, holiday shopping, and plenty of festive snacks and sips.

Shangri-La Lobby Lounge and Bar

You had us at Fireside Festive Cocktails. Three words that sum up our vision of the perfect holidays, these also signal the moment that Shangri-La Toronto's Lobby Bar transforms into one of the city's most festive spaces. You'll want to toast to every moment with a Naughty and Nice or Snow Ace in hand.

Shangri-La Lobby Lounge and Bar

You had us at Fireside Festive Cocktails. Three words that sum up our vision of the perfect holidays, these also signal the moment that Shangri-La Toronto's Lobby Bar transforms into one of the city's most festive spaces. You'll want to toast to every moment with a Naughty and Nice or Snow Ace in hand.

One King West

Get some quality time in with the big guy at One King West's Santa's Brunch. Taking place on December 10th, in the hotel's super-swank Grand Banking Hall, the brunch combines a vast spread of sweet and savoury treats with games, balloons and a memorable visit with Santa himself. To book a table, visit Onekingwest.com.

One King West

Get some quality time in with the big guy at One King West's Santa's Brunch. Taking place on December 10th, in the hotel's super-swank Grand Banking Hall, the brunch combines a vast spread of sweet and savoury treats with games, balloons and a memorable visit with Santa himself. To book a table, visit Onekingwest.com.

Miracle

Returning this year, Miracle combines a riotously bedecked room with cocktails from the Civil Liberties team. Yes, they have names like Jingle Balls Nog and Christmapolitan, but each festive offering is a as balanced and delicious as you'd expect from such an esteemed group. Plus, with a dollar from each drink sold benefitting Nellie's Shelter, you'll be giving back as you knock them back.

Miracle

Returning this year, Miracle combines a riotously bedecked room with cocktails from the Civil Liberties team. Yes, they have names like Jingle Balls Nog and Christmapolitan, but each festive offering is a as balanced and delicious as you'd expect from such an esteemed group. Plus, with a dollar from each drink sold benefitting Nellie's Shelter, you'll be giving back as you knock them back.

Little Sister - Java Jingle

Until January, toast to the holidays at Java Jingle — Little Sister's holiday-themed pop-up bar. Taking place at both of the restaurant's locations (on Portland and Yonge), the pop-up promises to draw guests in with holiday music and festive decor before they dive into a roster of cheery cocktails and the restaurant's superlative menu of Dutch-Indonesian fare. Visit Resy.com to book your table.

Little Sister - Java Jingle

Until January, toast to the holidays at Java Jingle — Little Sister's holiday-themed pop-up bar. Taking place at both of the restaurant's locations (on Portland and Yonge), the pop-up promises to draw guests in with holiday music and festive decor before they dive into a roster of cheery cocktails and the restaurant's superlative menu of Dutch-Indonesian fare. Visit Resy.com to book your table.

Kimpton Saint George

Even the shopping allergic will find plenty to love at the Kimpton Saint George's annual Holiday Market Sip 'N' Shop. Buoyed by wine, coffee, light bites, beautiful surroundings and a number of local vendors, they might even get everything they need in one delightful day.

Kimpton Saint George

Even the shopping allergic will find plenty to love at the Kimpton Saint George's annual Holiday Market Sip 'N' Shop. Buoyed by wine, coffee, light bites, beautiful surroundings and a number of local vendors, they might even get everything they need in one delightful day.

Hotel X

On December 9th and 10th, 16th and 17th, treat tiny tots to breakfast with the couple of the hour at Hotel X's Breakfast with Santa and Mrs. Claus. Beyond stories, selfies, face painting and the chance to hand-deliver letters to the big guy, kids and their families will enjoy a breakfast spread overflowing with holiday favourites — from candy cane pancakes to holiday yogurt parfaits. To book your table, visit Eventbrite.ca.

Hotel X

On December 9th and 10th, 16th and 17th, treat tiny tots to breakfast with the couple of the hour at Hotel X's Breakfast with Santa and Mrs. Claus. Beyond stories, selfies, face painting and the chance to hand-deliver letters to the big guy, kids and their families will enjoy a breakfast spread overflowing with holiday favourites — from candy cane pancakes to holiday yogurt parfaits. To book your table, visit Eventbrite.ca.

Holts Café Bloor Street

Inspired by British Fragrance House Jo Malone's holiday scents, Holts Café's new afternoon tea is a journey through the aromas of the season. Ginger and orange, pine and spice perfume a flurry of tasty treats, from finger sandwiches and scones to holiday cupcakes and bonbons. Book your table at Holts Café Bloor at Holtrenfrew.com.

Holts Café Bloor Street

Inspired by British Fragrance House Jo Malone's holiday scents, Holts Café's new afternoon tea is a journey through the aromas of the season. Ginger and orange, pine and spice perfume a flurry of tasty treats, from finger sandwiches and scones to holiday cupcakes and bonbons. Book your table at Holts Café Bloor at Holtrenfrew.com.

Fairmont Royal York

Sit shoulder-to-shoulder with like-minded revellers at Fairmont Royal York's The Thirsty Elf pop-up, taking place between November 22nd and December 22nd. There, you'll encounter a surfeit of festive drinks — with names like Winter Wonderland and Christmoose S'More — and a surplus of garlands and ornaments, ribbons, cozy vibes, and an opportunity to wear your most hideous holiday sweater, shamelessly. Walk-in only, you'll want to plan accordingly.

Fairmont Royal York

Sit shoulder-to-shoulder with like-minded revellers at Fairmont Royal York's The Thirsty Elf pop-up, taking place between November 22nd and December 22nd. There, you'll encounter a surfeit of festive drinks — with names like Winter Wonderland and Christmoose S'More — and a surplus of garlands and ornaments, ribbons, cozy vibes, and an opportunity to wear your most hideous holiday sweater, shamelessly. Walk-in only, you'll want to plan accordingly.

Epoch

Gift wrapping — and unwrapping — can be thirsty work. Recover your strength with the elegance and exquisite bites of EPOCH's Festive Afternoon Tea. Offered on various dates throughout the season, it's the most serene counterpoint to the holiday hoopla. To reserve, visit OpenTable.com.

Epoch

Gift wrapping — and unwrapping — can be thirsty work. Recover your strength with the elegance and exquisite bites of EPOCH's Festive Afternoon Tea. Offered on various dates throughout the season, it's the most serene counterpoint to the holiday hoopla. To reserve, visit OpenTable.com.

Eataly Toronto

Have the happiest of holidays — one bite of prosciutto at a time — at Eataly Yorkville's Holiday Taste-Around, on December 7th. An event that lets guests explore la bella vita through classic Italian holiday flavours, this one will have you feasting on velvety pasta, authentic pizza, cream-filled cannoli, tender panettone, and more, all night long. For tickets, visit Eventbrite.ca.

Eataly Toronto

Have the happiest of holidays — one bite of prosciutto at a time — at Eataly Yorkville's Holiday Taste-Around, on December 7th. An event that lets guests explore la bella vita through classic Italian holiday flavours, this one will have you feasting on velvety pasta, authentic pizza, cream-filled cannoli, tender panettone, and more, all night long. For tickets, visit Eventbrite.ca.

d|bar

From December 23rd to 26th, tuck into a festive fondue board at D|Bar. Whether you opt for traditional (with baguette, charcuterie, Brussels sprouts and a pot of molten cheese) or the Yorkville board (which arrives with lobster, shrimp, stirploin, and more), your tipple of choice will be in excellent company. To reserve, visit dbartoronto.com.

d|bar

From December 23rd to 26th, tuck into a festive fondue board at D|Bar. Whether you opt for traditional (with baguette, charcuterie, Brussels sprouts and a pot of molten cheese) or the Yorkville board (which arrives with lobster, shrimp, stirploin, and more), your tipple of choice will be in excellent company. To reserve, visit dbartoronto.com.