Good afternoon — Toronto just launched a new waterfront shuttle, Zellers is officially returning near Yorkdale, and the city is already studying new fixes for one of Toronto’s most frustrating intersections.

Meanwhile, the province is taking over the Gardiner and DVP, a massive redevelopment above the downtown rail corridor is in the works, and the latest list of Toronto’s worst roads is out.

Plus: Only 3 spots left! Sign up for our online lecture on Unbuilt Toronto Streets, Squares, & Landmarks. Reserve your spot here.

Let’s get into it.

THE DIGEST: 7 Handpicked Stories

🌊 New Waterfront Shuttle: A new east-west water shuttle is now connecting three stops along Toronto’s waterfront, including Ookwemin Minising, Yonge Slip, and Portland Slip. The pilot program aims to test the future of water-based transit, with trips taking about 30 minutes end-to-end and special $5 fares available during FIFA World Cup match days.

🛍️ Zellers Returns: The iconic Canadian retailer Zellers is opening a new Toronto store near Yorkdale Mall on June 18 as part of its national comeback. The revived brand promises a mix of nostalgic favourites, including the return of Zeddy, alongside grocery items, home goods, and expanded merchandise offerings.

📍Direct To Muskoka: FlixBus is launching a new direct route from Toronto to Muskoka and North Bay starting June 8. The seasonal service will connect travellers to popular cottage country destinations including Gravenhurst, Bracebridge, and Huntsville, with one-way fares starting at under $50.

🚧 Worst Roads: The latest CAA Worst Roads survey has named five Toronto streets as the city’s roughest drives for 2026: Steeles Avenue East, Sheppard Avenue West, Bathurst Street, Unwin Avenue, and Eglinton Avenue West. Toronto also claimed four spots in Ontario’s top 10 list, highlighting ongoing concerns over road conditions and infrastructure maintenance.

🚘 Gardiner And DVP: The Ontario government will assume ownership and maintenance of Toronto’s Gardiner Expressway and Don Valley Parkway in 2027. Provincial officials say the move will ease financial pressure on the city while supporting future transportation and infrastructure investments.

🛣️ Another Redesign: The City of Toronto is studying new ways to reduce congestion at the busy Eglinton Avenue West and Allen Road intersection, including options such as a pedestrian bridge, roundabout, tunnel, and new cycling infrastructure. The review comes just a few years after the intersection reopened following a decade of disruption tied to Crosstown LRT construction.

🏗️ Rail Corridor Proposal: A proposed redevelopment above Toronto’s downtown rail corridor has unveiled new plans featuring eight towers, nearly 4,000 homes, office space, retail, and more than two acres of parkland. The ambitious project would transform the area between Bathurst and Spadina while creating new transit connections and thousands of construction jobs.

MORE YOU NEED TO KNOW

🏴‍☠️ Pirate Ship Hits Market: A pirate-themed tour boat operating along Toronto’s waterfront has been listed for sale, giving aspiring entrepreneurs a chance to take over one of the city’s most unusual attractions. The vessel has become a familiar sight on the harbour and is being marketed as a turnkey tourism business.

🤖 AI & Elections: A new Toronto petition is calling for rules governing the use of AI-generated images, videos, and audio in municipal elections. Supporters argue the technology is increasingly being used to influence debates on issues like bike lanes and transit, while critics say AI content can blur the line between political messaging and misinformation.

⚽️ Expect Worse Traffic: Experts say Toronto should prepare for heavier congestion during the FIFA World Cup as matches overlap with Pride, Canada Day celebrations, Blue Jays games, concerts, and other major events. Officials warn that downtown travel will not be "business as usual" during the tournament.

June 25 | 8:00 PM - 9:00 PM (online)
Reserve your spot here (only 3 spots left)

LOST TORONTO:
Yonge & Front Aerial 1950s (Redeveloped)

Downtown Toronto in the 1950s before most of these buildings were bulldozed.

Across from the O'Keefe Centre rendering (Meridian Hall today), you can see the old Toronto Board of Trade Building (demolished in 1958).

Behind the Gooderham Building, you can see the beautiful Victorian buildings that were demolished in the 1960s to make way for the failed St Lawrence Centre development.

That land was initially a parking lot, and today it's Berczy Park.

THINGS TO DO IN TORONTO: THE ‘INSIDER’ SCOOP

Editor’s Pick! Only 3 Spots Left! Toronto Streets, Squares, & Landmarks That Were Never Built - A limited-seat online history lecture exploring the ambitious plans that could have radically changed the city’s landscape. The one-hour presentation examines Toronto projects that existed only on paper, from proposed boulevards and public squares to monumental buildings and large-scale urban renewal schemes that were ultimately abandoned.
June 25 | 8:00 PM – 9:00 PM
Location: Online (3 spots left)

Taste of Little Italy - Taste of Little Italy returns to College Street for a weekend celebrating food, music, and culture in one of Toronto’s most vibrant neighbourhoods. The annual street festival transforms College Street into a pedestrian-friendly destination filled with restaurant patios, food vendors, live entertainment, and family-friendly activities.
June 12 | 3:00 PM – 11:00 PM
June 13 | 12:00 PM – 11:00 PM
June 14 | 12:00 PM – 10:00 PM
Location: College Street (Bathurst St to Shaw St)

Toronto Blue Jays Roy Halladay Replica Jersey Giveaway - The Toronto Blue Jays will celebrate the legacy of Roy Halladay with a special giveaway night at Rogers Centre. The first 15,000 fans through the gates will receive a replica retro Halladay jersey, honouring one of the most iconic pitchers in franchise history.
June 8 | 7:07 PM – 10:07 PM
Location: Rogers Centre, 1 Blue Jays Way

Luminato Festival 2026 - Luminato Festival returns in June 2026 for a special 20th anniversary edition, marking two decades as one of Toronto’s premier arts and culture festivals. Spanning nearly a month, the festival will feature performances, exhibitions, and creative collaborations with many of the city’s leading arts organizations.
June 3 – 28
Location: Multiple Venues Across Toronto

Breathtaking Gardens at Casa Loma - A new summer wellness series that combines movement, music, and mindfulness in the castle’s historic gardens. Running on Sunday mornings throughout the summer, the program is designed to help participants recharge through a blend of yoga, Pilates, somatic movement, and live music.
June 7 – August 30 (Sundays) | 9:00 AM – 11:00 AM
Location: Casa Loma, 1 Austin Terrace

Island Eats Food and Travel Festival - Island Eats Food & Travel Festival returns to Mel Lastman Square for a weekend celebrating Caribbean food, music, culture, and travel. The free festival brings together authentic cuisine, live entertainment, cultural performances, and interactive experiences inspired by destinations across the Caribbean.
June 13 | 1:00 PM – 10:00 PM
June 14 | 1:00 PM – 8:00 PM
Location: Mel Lastman Square, 5100 Yonge St

A True Canadian Welcome at the Hockey Hall of Fame - A True Canadian Welcome at the Hockey Hall of Fame is a special one-day celebration bringing together the spirit of hockey and the excitement of international soccer as Toronto welcomes visitors from around the world. The event highlights Canada's love of sport through a morning of free activities, giveaways, and classic Canadian treats.
June 12 | 7:30 AM – 11:00 AM
Location: Hockey Hall of Fame, 10 Front St W

RECOS: Things you will love for around $50

📸 Nostalgia: Capture moments like it’s the 90s
🦫 Toronto: Canada’s most famous arena
🦮 Dogs: Be seen at night
🧑‍🍳 Kitchen: Add some colour to your kitchen
🐈 Pets: No more dirty paws
InsiderToronto may collect an affiliate fee on these items

VIDEO OF THE WEEK

Is the 401 really the world’s busiest highway? We explore the stats and the story behind how a simple 4-lane highway turned into a monster system.

Here is the link: Click here to watch

MAP OF THE WEEK

This map from 1915 shows how Toronto grew by annexing nearby villages and towns. One of my favourite visual representations of early Toronto expansion.

Here is the link: Click here to see the map

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