Toronto’s Playground Keeps Going as The Bentway Launches Late-Summer Programming

With roller skating, family programming, art socials and a new after school series, The Bentway keeps Toronto’s summer momentum going into fall.

Summer isn’t over at The Bentway. Following a high-energy and widely celebrated run as part of the official World Cup celebrations in Toronto, The Bentway is keeping the momentum rolling with a new lineup of late-summer and fall programming that invites Torontonians to keep playing, creating, and exploring the city together. 

Swapping cleats for skates, The Bentway’s iconic 220-metre figure-eight Skate Trail returns from August 7 through September 27, bringing back roller skating under the Gardiner alongside a season of community-driven events including skate parties, beginner lessons, art workshops, family programming, and the launch of a brand-new after school program for young city-builders. 

“The energy of the World Cup doesn’t end with the final match–it lives on in the public spaces where people continue to gather, play, and connect. Whether you’re lacing up roller skates for the first time, making art with friends old and new, taking your family on a Dino Run, or discovering a new perspective on Toronto through our After School program, we’ve designed experiences for people of all ages that celebrate movement, creativity, exploration, and time spent together in public space.”

– Anna Gallagher-Ross, Director of Programming at The Bentway

The Bentway is making it easier than ever to roll into the season, with on-site roller skate rentals available for visitors looking to experience one of Toronto’s most unique outdoor skating destinations. 

The season kicks off on August 7 with the return of The Bentway’s legendary Roller Skate Party, co-hosted with BEATS + SKATES and The Melanin Skate Crew. The free community celebration will feature DJs, live painting, skate performances, vendors, and a high-energy opening night that sets the tone for the rest of the season. A limited 2-for-1 roller skate rental promotion will be available during the event while supplies last. 

Visitors can also roll into weekly Roller Skate Lessons every Friday night through September, designed for beginners looking to build confidence and learn the basics on wheels. 

For families, Dino Run at The Bentway return on August 22 and September 19, transforming the Skate Trail into a prehistoric adventure complete with dinosaur specialists, storytelling, games, and a family-friendly chase around the track. 

Beyond the Skate Trail, The Bentway’s popular Art Socials continue through August at The Bentway Studio in partnership with Noble Space, offering weekly beginner-friendly creative workshops ranging from collage and textile-making to watercolour and printmaking. 

Looking ahead to fall, The Bentway will also returns with Bentway After School, a new educational program developed with Maximum City. Running in three five-week sessions from September through December, the program invites youth ages 8 to 14 to explore urban design, placemaking, ecology, and storytelling through hands-on activities, neighbourhood investigations, and recreation. 

program highlights

PROGRAM HIGHLIGHTS 

Roller Skate Party: In collaboration with BEATS + SKATES, and The Melanin Skate Crew 
August 7, 2026
6:30 p.m. – 10:00 p.m. 
FREE 
Expect a special 2-for-1 offer on roller skate rentals, Mrii and DJ QC behind the decks, live painting by La Pupila, and a skate trail performance by local legends, Scandl.us. Explore Toronto Queer Market vendors, group skate demonstrations, and enjoy the best summer night vibe.

The Bentway Skate Trail + Skate Rentals
August 8 – September 27, 2026
Fridays: 5:00pm. – 9:00pm.
Saturdays & Sundays: 1:00pm – 8:00pm
Skating is free  
Rentals start at $18 (plus tax)  

Roller Skate Lessons
Fridays, August 7 – September 25, 2026 
Two sessions: 6:30pm-7:30pm or 7:30pm-8:30pm.
Registration required: https://thebentway.ca/event/roller-skate-lessons-2026/  
$15 (equipment rentals not included) 

Art Socials in partnership with Noble Space 
Tuesdays through August 25, 2026 at The Bentway Studio (55 Fort York Blvd) 
Connect, create, and unwind at The Bentway’s weekly Art Socials. Hosted by Noble Space, these beginner-friendly workshops offer a welcoming space to try new artistic practices, meet fellow creatives, and spend summer evenings making art together. 
Jul 21 Collage: ReExpressway Edition 
Aug 4 Watercolour Painting: Toronto Skies 
Aug 11 Printmaking: Letterpress Postcards from Toronto 
Aug 18 Collage: ReExpressway Edition 
Aug 25 Drawing: Art Games! 
Registration required: https://thebentway.ca/event/art-socials/  
$15 (plus fees) 

Dino Run at The Bentway
August 22 & September 19, 2026 
This fun-filled morning starts with costumed Dino Specialists teaching participants about dinosaurs through song, dance, storytelling, and games. Then, the kids will set out as Dino Explorers on an exciting, non-competitive chase to recapture runaway dinosaurs. 
Registration required: HERE. 
$25 (plus fees) 

Bentway After School
September 8 – December 15, 2026 at The Bentway Studio (55 Fort York Blvd) 
$175 per five-week cohort