Good afternoon — New skyscrapers are set to reshape Toronto’s waterfront, Air Canada’s bringing more U.S. flights to Billy Bishop, and the Jays are chasing history in their first World Series since ’93.

Meanwhile, police are cracking down on downtown gridlock, farmers are facing a pumpkin shortage, and the Hudson’s Bay Company is auctioning off some of Canada’s most historic art.

Let’s get into it.

THE DIGEST: 7 Handpicked Stories

🏙️ Toronto’s next supertalls: Developer Pinnacle International has unveiled new plans for massive towers at One Yonge, set to rise 80 and 85 storeys tall, nearly 300 metres each, along the city’s waterfront. The project, part of the growing Pinnacle One Yonge megacomplex, already home to Canada’s soon-to-be tallest building. If built, the skyscrapers would rank among Toronto’s three tallest buildings.

💸 Price of glory: As the Toronto Blue Jays face the Los Angeles Dodgers in the World Series, ticket prices are soaring. With only 44,000 seats available at Rogers Centre, fans are left priced out — and some say it’s now cheaper to fly to Los Angeles than see a home game.

🚦 Toronto crackdown: Police have launched a three-month blitz to curb gridlock downtown by targeting drivers who “block the box,” stop illegally, or park in rush-hour lanes. The campaign, running weekdays from 3–7 p.m. between Bloor, Front, Bathurst, and Jarvis, could see fines up to $615 and vehicles towed.

✈️ Air Canada expands at the Island: The airline is making its biggest Billy Bishop expansion in 35 years, launching new U.S. routes to New York, Boston, Chicago, and Washington starting spring 2026. Air Canada is also boosting domestic service, increasing Montreal flights to nine daily and Ottawa to six.

🌉 A new skyline icon is rising: Construction is underway on the Don Valley Crossing, a massive bridge that will carry the Ontario Line across the Don River — Toronto’s largest new bridge in nearly a century. Standing 38 metres above the valley, the cantilever-style structure will link Thorncliffe Park to the city’s core, offering a dramatic new sightline beside the historic Leaside Bridge.

🎃 Pumpkin problems: Farmers across the province are reporting one of the worst pumpkin yields in decades, blaming the hot, dry summer and lack of rain for stunted crops. Some, like Niagara’s Warner Ranch, say it’s “too little, too late” after months of drought. Many farms still have plenty of pumpkins, but expect smaller sizes this fall.

🖼️ Historic HBC art heads to auction: On Nov. 19, the Hudson’s Bay Company will auction off some of its most prized paintings, a once-in-a-lifetime event for Canadian art collectors. Highlights include Frederic Marlett Bell-Smith’s Lights of a City Street ($100K–$150K) and Winston Churchill’s Marrakech ($400K–$600K). Auctioneer David Heffel calls it, “the most high-profile art sale in Canadian history.”

MORE YOU NEED TO KNOW

🍕 Blaze flickers out in Toronto: LeBron James–backed Blaze Pizza has closed nearly all of its Toronto locations, leaving just one at Yonge and Sheppard. The chain debuted at Yonge-Dundas Square in 2015 with its build-your-own pies but has now shuttered its flagship and John Street spots.

🥶 Cold snap: Toronto is about to feel below zero for the first time this season. According to The Weather Network, temperatures will dip just in time for the World Series opener at Rogers Centre. The chill will linger through the weekend, with overnight lows near freezing until mid-next week.

🎶 Free concerts hit Toronto: A concert series called Sound Break is bringing free noon-hour performances to downtown and uptown venues every Thursday from Oct. 23 to Dec. 18. Hosted by TO Live, the shows will rotate between Meridian Hall, Meridian Arts Centre, and the St. Lawrence Centre for the Arts, featuring talent across genres.

LOST TORONTO:
Spadina and College

Then: Looking north from Spadina and College. At one time, it was crowned by opulent bank buildings on three corners and a magnificent church by architect E.J. Lennox on the fourth. Completed in 1889, the Broadway Methodist Tabernacle was a Romanesque Revival church designed by E.J. Lennox. The old Knox College sits at the centre of the photo.

Now: Only the former Knox College (1 Spadina Crescent) remains. The church was closed following the formation of the United Church in 1924 and demolished by 1930. A four-storey office building now occupies the site where this once-prominent landmark stood.

THINGS TO DO IN TORONTO: THE ‘INSIDER’ SCOOP

Editor’s Pick! Darkfield Toronto brings spine-tingling sensory theatre to STACKT Market this fall with SÉANCE and FLIGHT—two immersive, audio-driven experiences performed in total darkness. Created by UK-based DARKFIELD and presented by Realscape Productions, these shows plunge audiences into alternate realities using binaural 360° sound, environmental effects, and pitch-black shipping containers.
Until November 9 | 5:00 PM – 9:00 PM
Location: STACKT market, 28 Bathurst St

Evening Ghost Tour at Ontario's Legislative Building - Step inside Ontario’s historic Legislative Building after dark for a rare nighttime tour filled with mystery, folklore, and spine-tingling stories. This 60-minute guided experience explores the unexplained happenings and ghostly tales that haunt the halls of Queen’s Park, all while giving you exclusive after-hours access to one of the province’s most iconic buildings.
October 25 | 2:00 PM – 3:00 PM
October 29 & 30 | 6:30 PM – 7:30 PM
Location: Ontario Legislative Building, 111 Wellesley St. West

2025 Canadian Women's Squash Open - Watch the world’s top squash players go head-to-head in the heart of Toronto at the 2025 Canadian Women’s Squash Open. Held inside the stunning Allen Lambert Galleria at Brookfield Place, this high-energy PSA World Tour event promises fast-paced matches, elite competition, and a court-side experience like no other—all in a uniquely urban setting.
October 25 | 12:00 PM – 3:00 PM & 5:00 PM – 8:00 PM
October 26 | 12:00 PM – 3:00 PM & 5:00 PM – 8:00 PM
October 27 – 29 | 5:30 PM – 8:30 PM
October 30 | 6:30 PM – 8:30 PM
Location: Allen Lambert Galleria, Brookfield Place, 181 Bay Street

Toronto Art Crawl Christmas Market - Toronto’s largest one-day outdoor Christmas Market is back for its 11th year—just in time for the holiday season. Head to The Bentway for a festive shopping experience featuring over 140 artists and artisans, live art demos, and delicious eats. With one-of-a-kind gifts and local creators, it’s the perfect spot to get a head start on your holiday list.
November 1 | 11:00 AM – 6:00 PM
Location: The Bentway, 250 Fort York Blvd

13 Rooms - Step into the shadows at 13 Rooms, an immersive Halloween walkthrough that dares you to journey through 13 terrifying spaces—each more unnerving than the last. Packed with cinematic effects, chilling soundscapes, and live actors lurking in every corner, this isn’t just a haunted house—it’s a photo-ready fright fest perfect for content creators and thrill seekers alike.
Until November 1 | 6:00 PM – 11:00 PM
Location: Cloverdale Mall, 250 The East Mall

World Series! Jays vs. Dodgers (schedule):
⚾️ Game 1: October 24 | 8:00 PM
⚾️ Game 2: October 25 | 8:00 PM
⚾️ Game 3: October 27 | 8:00 PM
⚾️ Game 4: October 28 | 8:00 PM
⚾️ Game 5: October 29 | 8:00 PM
⚾️ Game 6: October 31 | 8:00 PM*
⚾️ Game 7: November 1 | 8:00 PM*
*if necessary
Tied Leads 1-1
Get your Jays gear here!

RECOS: Things you will love for under $40

💡 Lighting: This has 16 million colours
🦮 Dogs: Don’t walk your dog at night without this
❄️ Cold: The one glove for cold walks
🦝 Toronto: The one book on Toronto history
🔪 Cooking: Why you need this carbon steel
InsiderToronto might collect an affiliate fee on these items

VIDEO OF THE WEEK

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