"The market doors swing wide open for the coziest weekend of the season." That line describes December 5 and 6 on the Leslieville Christmas Pop-Up Market's page, and it fits the whole stretch from late October to the end of the year. Queen Street East keeps its event calendar busy after Halloween. The events move indoors. For the next ten weeks, things happen in a food hub on Gerrard, the upper floors of a community centre and more than 25 shop windows. Only a few of them need tickets bought in advance.
The handoff happens on one Sunday.
October 25 Runs Two Neighbourhood Traditions at Once
Sunday, October 25 is the last outdoor day of the year for the Leslieville Farmers' Market, which runs 9 a.m. to 2 p.m. at Greenwood Park, 150 Greenwood Ave. The Riverside Halloween Fest is the same day, at Joel Weeks Park, 10 Thompson Street, just north of Queen. The market closes at 2 p.m. and the Halloween Fest's family program runs until 3, so you have time to do both if you start early.
The Riverside BIA schedules the afternoon in layers:
- 11 a.m. to 3 p.m. Free family activities at Joel Weeks Park, while quantities last. There's a pumpkin patch with pumpkin decorating, cupcake decorating, cotton candy, henna, face painting, crafts from the Riverside BIA and the Queen/Saulter Library Branch, and a set from DJ Stevie Kicks. A local vendors' Halloween market runs alongside.
- Noon to 3 p.m. Painting on canvas with D&A Creative Toronto.
- Noon to 2 p.m. The Riverside Halloween Dog Costume Contest and Pawty, with judging and prizes.
- 1 to 3 p.m. A robot dog activation and selfie station.
- 3 to 4 p.m. The Riverside Candy Crawl and Costume Parade. It leaves Joel Weeks Park, follows the Queen Street East sidewalks with treat stops at more than 10 local businesses, and ends with storytime from the Queen/Saulter branch of the Toronto Public Library.
Entry is free, but the organizers ask people to get free tickets and RSVP through the event page. The parade is the one part that happens on Queen itself. After this, the season's activity moves off the grass and indoors.
The Market Moves to Gerrard
The farmers' market keeps going after October. From November 1 to December 20, it runs indoors every Sunday, 9 a.m. to 2 p.m., at the East End Food Hub, 1470 Gerrard St. E. That's eight Sundays in a row, with the same hours as summer, at a different address. The market's season page then lists another stretch from February 28 to May 2, which suggests a gap from late December to the end of February.
So your Sunday morning shop doesn't stop when the weather turns. It moves north to Gerrard, and for the last two Sundays it gets a long way through December.
The Riverside Stretch Turns Into a Gallery
On November 23, the Riverside BIA starts Window Wonderland, with more than 25 holiday windows by local artists on storefronts along Queen St. E. from Davies Ave. to De Grassi St. Visitors can follow an online map, vote for favourites and enter a raffle for local prizes until December 15. Voting ends on December 15, but the BIA says the art will stay up until at least December 31. Through the last two weeks of the year, a walk along that stretch passes a full display of artist windows, even after the contest is over.
The east end of that stretch runs into construction. Metrolinx's notice for Ontario Line support-column work at Leslieville Station runs from September 7, 2026 to May 28, 2027, mostly on weekdays from 7 a.m. to 7 p.m. The notice says the work stays within the site, minor traffic delays nearby are possible, and no transit impact is expected. A City report dated June 19, 2026 also set out planned north-side sidewalk and westbound curb-lane closures on Queen East near De Grassi from August 1, 2026 through December 31, 2028. If you're walking the windows from west to east, the last block may have hoarding on one side. Weekends, when the column work is mostly paused, are the quieter time to finish the route.
November 29 Is Riverside's Big Day
Window Wonderland's free guided tour is on Sunday, November 29. The BIA hasn't published a start time yet. The Riverside Holiday Market is the same day, 11 a.m. to 4 p.m., at Ralph Thornton Community Centre, 765 Queen St. E. It fills the second and third floors with local vendors, free Santa photos, live music, hot chocolate, and crafts and treats for kids.
That Sunday has the pattern of the whole season in small form. The tour stays outside on the sidewalk, and the market is indoors upstairs, a few blocks from the windows. The East End Food Hub market also runs that morning, 9 a.m. to 2 p.m., so you could visit all three in one day.
December 4 to 6 Belongs to Leslieville
A week later, the season's center shifts east. The Leslieville Christmas Pop-Up Market runs December 4 to 6, and it has two very different parts:
Friday, December 4, 6 to 10 p.m. An all-inclusive opening night with a tasting passport for wines, spirits, craft beers, ready-to-drink options and spirit-free drinks. There's an aerial silks performance by Artist's Play, food vendor sampling, Christmas photo ops, and DJ Spence Diamonds playing '80s and '90s hits.
Saturday and Sunday, December 5 and 6, 10 a.m. to 6 p.m. Free entry, more than 70 artisan and small-brand vendors, and new vendors each day.
The organizers also list Santa Village, with photos and a workshop where kids write and send letters to Santa, plus candle-making and ornament-making workshops and Christmas carollers.
The 2026 venue hasn't been announced yet. The page says "More Details to Come!" and that November 2026 is when announcements arrive. Last year's event used a different address. Until the organizers confirm this year's location, check the market's page before you head out rather than going to last year's spot.
The Ticket Dates Matter More Than the Event Dates
Almost everything above is free and drop-in. The Queen East Eats fall food tours are the exception. The Leslieville BIA and Riverside BIA run them with Delicious Discoveries Food & Walking Experiences. Each tour visits six pre-selected local food and drink spots in Riverside and Leslieville with a guide, and costs $10 plus fees. The October 3 tour sold out.
Tickets for each remaining tour go on sale on a set date on Eventbrite. Sales close when the tour sells out or on a cutoff date, whichever comes first:
- Saturday, November 14, 1 to 3 p.m. Tickets on sale November 4, cutoff November 10.
- Saturday, December 5, 1 to 3 p.m. Tickets on sale November 20, cutoff December 1.
- Saturday, December 12, 1 to 3 p.m. Tickets on sale December 1, cutoff December 8.
The December 5 tour falls on the first free day of the Leslieville Christmas Pop-Up Market, so you can book the 1 p.m. tour and shop the market before or after. The organizers note that if a tour isn't showing on Eventbrite yet, its tickets haven't been released. The program is funded through the City of Toronto and FedDev Ontario's Dining Districts Grant Stream 2.
Gaps in the Leslieville Calendar So Far
A few traditional fixtures aren't confirmed yet. We found no 2026 date for a Leslieville BIA tree lighting or Wanderlust evening. The most recent edition we could verify was in 2024, with a tree lighting at Leslie Grove Park, at Queen St. E. and Jones Ave. The Leslieville BIA's events page at visitleslieville.ca is the place to check. The BIA is also working on a Streetscape Master Plan, which had a virtual public meeting on October 6 and is meant to recommend near-, medium- and long-term public-realm improvements for the strip.
Here are the dates that are confirmed, with the shopping dates on one list:
- November 4: November 14 food tour tickets go on sale
- November 20: December 5 food tour tickets go on sale
- December 1: December 12 food tour tickets go on sale
- December 20: Last indoor farmers' market Sunday at 1470 Gerrard St. E. before the break
Questions about how this part of Queen East is changing, from the station construction near De Grassi to the BIA's streetscape plan, often come up in our conversations with Leslieville and Riverside homeowners. If you'd like to know how the street around your home is changing and what that means for its value, Nancy Hate can help. Request a complimentary home valuation.
