Fall & Holiday Happenings in Toronto

Oct 8

Written By C

Summer may get most of the attention in Toronto, but the last few months of the year have plenty going on too. The ballet and symphony seasons are back, theatres are filling up, the Leafs and Raptors return, and before long the city starts to shift into full holiday mode.

Whether you’re looking for an exciting date night, an excuse to get dressed up, or something festive to do before the end of the year, here are a few things worth adding to your calendar.

BALLET & SYMPHONY

Fall also marks the return of Toronto’s major performing arts seasons, with some especially good options before the end of the year.

Romeo and Juliet

October 31 – November 8

The National Ballet of Canada opens its 75th anniversary season with John Cranko’s Romeo and Juliet, set to Prokofiev’s incredible score.

It’s also a particularly special revival. The production hasn’t been performed by the National Ballet since 2009, making this the first chance to see it in Toronto in more than 15 years.

The Music of Bond… James Bond

October 14 – 15

If traditional classical music isn’t usually your thing, this is an easy entry point into the Toronto Symphony Orchestra. The TSO is taking on six decades of James Bond music, from Goldfinger and Diamonds Are Forever to Skyfall, accompanied by vocalist Lena Hall.

A very good excuse for a martini and a night at Roy Thomson Hall.

James Ehnes Plays Tchaikovsky

November 26 – 29

For something more traditional, celebrated Canadian violinist James Ehnes performs Tchaikovsky’s Violin Concerto with the TSO, followed by Saint-Saëns’ dramatic Organ Symphony.

The Nutcracker

December 5 – 31

There are certain things that just feel like Christmas in Toronto, and The Nutcracker is one of them.

The National Ballet’s production has been a Toronto holiday tradition since 1995, complete with Tchaikovsky’s iconic score, elaborate sets and costumes, and the Sugar Plum Fairy.

If you’ve never been, this might be the year.

THEATRE

Toronto’s theatre calendar is particularly good this fall, with everything from award-winning new productions to unapologetic nostalgia.

Operation Mincemeat: A New Musical

October 27 – December 13

The Tony and Olivier Award-winning Operation Mincemeat makes its Canadian premiere at the Royal Alexandra Theatre this fall.

Based on the almost unbelievable true story of a British intelligence operation during the Second World War, the show turns an elaborate wartime deception involving a stolen corpse into a fast-moving musical comedy, spy caper and thriller.

Dirty Dancing: The Musical

November 24 – January 3

Dirty Dancing arrives at the CAA Ed Mirvish Theatre at the end of November, bringing Baby, Johnny, the summer of 1963 and all of the nostalgia of the original film to the stage.

13 Going on 30: The Musical

December 1 – January 24

Another dose of nostalgia, this time for anyone who grew up in the early 2000s. 13 Going on 30 has officially become a musical and arrives at the Princess of Wales Theatre in December.

Thirty, flirty and thriving... on stage.

CONCERTS

I’m keeping this list short. There are dozens of concerts coming through Toronto before the end of the year, but these are two of the bigger ones that caught my attention.

Journey

November 4 | Scotiabank Arena

Journey brings its Final Frontier Tour to Toronto in November. If Don’t Stop Believin’, Faithfully and Any Way You Want It are already permanently embedded in your brain, this one probably doesn’t require much explanation.

Trans-Siberian Orchestra

December 29 | Scotiabank Arena

For a much more over-the-top way to finish the holiday season, the Trans-Siberian Orchestra brings The Ghosts of Christmas Eve to Toronto for two performances on December 29.

Expect rock, Christmas music, lasers, pyrotechnics and a production that is about as subtle as you’d hope a Trans-Siberian Orchestra show would be.

SPORTS

Toronto Maple Leafs

Hockey season is back! And I love catching the action of Canada’s favourite pass-time live!

The Leafs have a busy home schedule through the rest of 2026, including:
New York Islanders – October 17 | 7:00 p.m.
San Jose Sharks – October 19 | 7:30 p.m.
Montreal Canadiens – November 7 | 7:00 p.m.
New Jersey Devils – November 8 | 7:00 p.m.
Colorado Avalanche – November 10 | 7:00 p.m.
Edmonton Oilers – November 14 | 7:00 p.m.
Los Angeles Kings – November 19 | 7:00 p.m.
Florida Panthers – December 3 | 7:00 p.m.
Anaheim Ducks – December 13 | 7:00 p.m.
Tampa Bay Lightning – December 19 | 7:00 p.m.
Washington Capitals – December 21 | 2:00 p.m.

Raptors Basketball

Basketball is almost back in Toronto, with the Raptors playing their first regular-season home game at Scotiabank Arena on October 21.

There are plenty of opportunities to catch a home game before the end of the year:

HOLIDAY HAPPENINGS

And then, seemingly overnight, Toronto turns into Christmas.

The Distillery Winter Village

November 12 – January 3

The Distillery District’s Christmas market returns November 12, transforming the cobblestone streets with holiday lights, vendors, seasonal food and drinks, carollers and one very photogenic Christmas tree.

The official tree-lighting ceremony takes place on opening night, November 12 at 6 p.m.

It gets extremely busy as Christmas gets closer, so I’m a fan of going earlier in the season when you can still enjoy the atmosphere without quite as much chaos.

Cavalcade of Lights

November 28 – January 7

Cavalcade of Lights marks the official start of the holiday season at Nathan Phillips Square, with Toronto’s Christmas tree, light installations, performances and skating.

Opening night is November 28, but the lights, select installations and skating continue into January. It’s also free, making it an easy addition to dinner or drinks downtown.

Between the Distillery Winter Village, The Nutcracker, holiday lights and skating downtown, December is when Toronto starts feeling genuinely festive.

There may be fewer patios and long summer nights, but there’s certainly no shortage of reasons to leave the house before the end of the year.