Upcoming Events By Date & Category
More To experience
Event Descriptions
MAY – JANUARY
I Heart Market Street
Join your neighbours on Market Street for live entertainment, pop up market vendors, seating and more! Market Street (Front Street to The Esplanade) is pedestrianized annually May – January.
June – August
Music in St. James Park
Join us during the summer on Thursdays (7-9 pm), at the Michael Comstock Pavilion in St. James Park for this free concert series. Bring a chair, or blanket for the back lawn, and pack a picnic to enjoy while local musicians take to the stage. Feel like dancing? Step on up and show us your moves.
Dates and artists are noted above in Upcoming Events.
June – August
Historic Reenactors & Artisans
On Saturdays, June through August, find historic reenactors and artisans in Old Town Toronto.
Reenactors: Each Saturday, 12pm-3pm, this friendly group tours the area and are happy to chat with you about historic facts, their period specific attire, or snap a selfie.
2026 Tentative Locations, Times & Activities:
12:30pm-1pm, Berczy Park for gossip and tea.
1pm-2pm, Market Street Stage for interactive quill writing.
2pm-3pm, St. James Park for a game of croquet.
Artisans: Each Saturday, 10am-1pm a different historical artisan sets up on the Market Street Stage to demonstrate their craft.
2026 Tentative Schedule:
June 6, Len Heidebrecht, The Cooper
June 20, Kelly Probyn-Smith, The Tinsmith
June 27, Lindsay Doran, The Wool Spinner
July 11, Len Heidebrecht, The Cooper
July 18, Peter Monahan, The Cobbler
August 1, Tammielyn Head, The Wool Spinner
August 15, Peter Monahan, The Cobbler
August 22, Kelly Probyn Smith, The Tinsmith
August 29, Tammielyn Head, The Wool Spinner
July
Music In Courthouse Square Park
New for 2026, join us Wednesdays in July, 6pm-8pm as a new music series is piloted in Courthouse Square Park. Enjoy these live concerts while dining on one of the restaurant patios circling the park, or sit and relax in one of the many park benches.
Dates and artists are noted above in Upcoming Events.
July – August
Berczy Beats
Join us in Berczy Park for live lunch time music Wednesdays, July and August. Eat your lunch next to the famous “dog fountain” and enjoy this free concert.
Dates and artists are noted above in Upcoming Events.
July – August
Yoga Classes in St. James Park
Our FREE Fitness Classes in St. James Park at the Michael Comstock Pavilion take place Tuesdays in July and August, from 6 – 7pm.
Designed to get you moving and enjoying our park, these fitness classes are offered free of charge thanks to Friends of St James Park and your local business community, represented by Old Town Toronto BIA.
Dates and class types are noted above in Upcoming Events.
July – August
Salsa On Market Street
A rhythm-infused series of events set to enliven the heart of Toronto’s Old Town this summer with Latin dance lessons, live music and tasty treats.
Friday July 17, 2026, 6pm-8pm
Friday July 24, 2026, 6pm-8pm
Friday July 31st, 2026, 6pm-8pm
August
Theatre In St. James Park
Join us in St. James Park for live theatre each August as we work with a local theatre to bring a new story to the Michael Comstock Pavilion stage.
Dates, play titles, and presenting local theatre noted above in Upcoming Events.
November
Post – Halloween Pumpkin Parade
Bring out your jack-o-lanterns to Berczy Park for the ultimate post-Halloween send-off. Let your creation glow with delight atop the park’s stage for all to see before bidding farewell to your pumpkin pal: to be composted with great reverence by the City of Toronto. Exact date will be noted above in Upcoming Events, once officially announced.
Date is noted above in Upcoming Events, once officially announced.
November – February
Cavalcade of Lights
Our annual Cavalcade of Lights takes place in Berczy Park, 35 Wellington St E, with lights on display from late November to early February. You are invited to attend our opening ceremonies each year with live music and warm smiles.
Dates are noted above in Upcoming Events, once officially announced.
January & May
DesignTO Festival & King East Design District Neighbourhood Hop
Old Town Toronto’s King East Design District plays host to DesignTO exhibitions each January, and one interactive event for industry insiders in early spring.
Dates are noted above in Upcoming Events, once officially announced.
Entertainer Application
Thanks for your interest in performing
We use Canada’s Music Incubator to do our booking. Our contact there is Sara Gomez.