Is this Toronto’s sweetest month ever?

Good afternoon — The city’s month-long Chocolate Festival is back, the Jays are in the playoffs (and ticket prices are downright scandalous), the long-delayed Crosstown might finally be moving, and a new discount megastore has shoppers lining up for hours.

Meanwhile, VIA’s direct train to Montreal has hit another snag and Toronto’s plane-spotting scene is taking off (we have the best spots).

Let’s get into it.

THE DIGEST: 7 Handpicked Stories

🚞 Direct train delayed: Via Rail has postponed its plan to launch nonstop Toronto–Montreal service, citing “operational constraints” with CN. The pilot, which would have cut stops in Kingston and other eastern Ontario cities, drew backlash from local officials. Via says it still plans to pursue direct trips, but communities want more consultation before service changes.

⚾️ Playoff sticker shock: Blue Jays fans are paying big to see their team’s first ALDS since 2016, with Ticketmaster seats starting at $262 for Game 1 and soaring past $3,000 in the lower bowl for a potential Game 5 at Rogers Centre. By contrast, Yankees tickets for the Bronx games are as low as $128 CAD on resale — though Canadians are blocked from buying them.

🍔 Shack attack at Yonge & Eg: Shake Shack is opening a new Toronto spot at 40 Eglinton Ave. E. on Oct. 3. It’s the chain’s latest move in a rapid GTA expansion, with upcoming locations at Vaughan Mills this fall and King St. W. and Yonge St. in 2026. Since arriving in Canada last year, Shake Shack has added Union Station, Yorkdale, and Square One.

🚧 Gardiner ahead of schedule: The City of Toronto says the Gardiner Expressway rehab is now six months ahead of schedule, with work between Dufferin and Strachan tracking for completion before the FIFA World Cup in June 2026. Originally slated for 2027, the project was fast-tracked with 24/7 construction and extra funding.

🚇 Crosstown update: After years of setbacks, the Eglinton-Crosstown LRT is finally edging closer to opening, with Metrolinx saying it hopes to begin its 30-day “revenue service demonstration” this week. The trial will run trains as if open to the public, a key step before launch.

🐼 Panda pandemonium: Toronto’s newest retail craze, Panda Mart, just opened its first Canadian store in Scarborough at 768 Warden Ave. The massive discount retailer, which sells everything from furniture and decor to shoes and electronics, drew huge crowds over opening weekend. Shoppers showed off finds like a marble dining set for under $200, while others warned of 2-hour checkout lines and empty shelves.

🛫 Plane spotting: Toronto Pearson Airport has quietly become a plane-spotter’s paradise, drawing crowds eager to watch giants like the Airbus A380 and Boeing 747 thunder just overhead. The best viewing spots? Airport Rd. & Orlando Dr., Dixie Rd. at Director Gate, and the Convair Dr. bend along the Etobicoke Creek Trail. It’s one of the loudest, most awe-inspiring free shows in Toronto.

MORE YOU NEED TO KNOW

✈️ Free booze, fewer worries?: After a rocky summer of strikes and passenger frustration, Air Canada is trying to win back travellers with perks: economy passengers now get complimentary beer and wine on all flights, plus new snacks like oat bars and ginger shots. But with tens of thousands still waiting on refunds, some wonder if a free glass of cabernet is really enough to smooth things over.

🎬 $4 Fall Flicks: Cineplex is bringing back its Family Favourites this October, offering $4 movie tickets for family-friendly classics every Saturday. The lineup includes Trolls, Minecraft, Trolls Band Together, and Tim Burton’s Corpse Bride. Tickets are $3.99 in-person or $5.49 online. A cheap, cozy way to spend your fall weekends at the movies.

🍫 Sweet 20th anniversary: The Toronto Chocolate Festival is back and bigger than ever, running all October long for its 20th year. Expect everything from chocolate-themed afternoon teas at the Omni King Edward Hotel to whisky-and-chocolate pairings, hands-on workshops, and a festive wrap party on Oct. 30 in Port Credit. What started in 2005 as a small chocolatier event has now grown into a full month of artistry and plenty of chocolate.

LOST TORONTO:
Fire Hall Number 14 (Demolished)

Toronto made a huge mistake here. This was Fire Hall Number 14. Completed in 1889 with a stunning clock tower. It was located at Bloor St W and Ossington Ave.

It was demolished in the early 1960s for the line 2 subway.

THINGS TO DO IN TORONTO: THE ‘INSIDER’ SCOOP

Editor’s Pick! Free Main Floor at ROM - The Royal Ontario Museum is opening its expansive main floor galleries for FREE! Explore world-class exhibits, ancient artifacts, and cultural treasures without spending a dime. Every weekend features a brand-new theme, with live pop-up performances, crafts, music, and hands-on activities led by Toronto’s local communities and artists.
October 1 – November 30 | 10:00 AM – 5:30 PM daily
Location: Royal Ontario Museum, 100 Queen’s Park

Pumpkin Fest Toronto - Get ready for four days of fall fun at PumpkinFest Toronto, a family-friendly outdoor festival packed with giant pumpkins, midway rides, inflatable mazes, train rides, and endless photo ops. Enjoy stage shows, carnival games, comfort food, and cozy vibes at Downsview Park over Thanksgiving weekend.
October 10 – 13 | 10:00 AM – 6:00 PM
Location: Downsview Park, 35 Carl Hall Road

The October Witch Market - Step into the mystical at the October Witch Market, taking over Made for Me Marketplace every weekend this fall. Browse rotating vendors offering potions, altar goods, crystals, candles, and more—plus tarot readings and flash tattoos every Saturday. A new spellbinding experience awaits each visit.
Every Saturday in October | 1:00 PM – 7:00 PM
Every Sunday in October | 12:00 PM - 6:00 pm
Location: Made for Me Marketplace, 1586 Dundas Street West

Sharks Exhibition at ROM - Dive into the deep at the ROM’s Sharks exhibition, a hands-on journey into the world of one of Earth’s most misunderstood creatures. Get up close with life-sized models, including the massive extinct Megalodon, and discover rare species like the tiny lanternshark. Explore shark anatomy, evolution, and conservation through dozens of interactive displays.
October 11, 2025 – March 22, 2026 | 10:00 AM – 5:30 PM
Location: Royal Ontario Museum, 100 Queen’s Park

Learn How to Take Better Digital Photos - Learn how to take better digital photos in this beginner-friendly workshop led by photographer Pascaline Le Bras. Held at S. Walter Stewart Library, this casual session will cover the basics of composition, smartphone camera tricks, and easy techniques to instantly level up your shots—no experience required, just bring your phone or digital camera!
October 9 | 4:00 PM – 6:00 PM
Location: S. Walter Stewart Library, 170 Memorial Park Ave

Chocolate Afternoon High Tea - Step into a Toronto tradition with Chocolate Afternoon Tea at The Omni King Edward Hotel. Since 1903, this historic hotel has elevated the art of Afternoon Tea with elegance, charm, and indulgent delights. Rekindle connections over rich chocolate treats, delicate finger sandwiches, and freshly steeped tea—all served in one of the city’s most iconic and opulent settings.
October 4 - 26 | Weekends Only (Call ahead)
Location: The Omni King Edward Hotel, 37 King Street East

ALDS Jays vs. Yankees (schedule):
⚾️ Game 1: October 4 | 4:08 PM
⚾️ Game 2: October 5 | 4:08 PM
⚾️ Game 3: October 7 | 8:08 PM
⚾️ Game 4: October 8 | 7:08 PM*
⚾️ Game 5: October 10 | 8:08 PM*
*if necessary
TOR leads 1-0
Get your Jays gear here!

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🦝 Toronto: The one book on Toronto history 
🪞 Decor: The hidden life of trees.
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VIDEO OF THE WEEK

This bird's-eye view map of Toronto from 1876 reveals a very different city!

Here is the link: Click here to watch

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