There’s a quiet kind of magic that settles over Winnipeg in the fall. The leaves turn gold, the air gets crisp, and suddenly we’re reaching for sweaters, slow mornings, and local traditions that feel just right. September invites us to pause, soak up the season, and reconnect with the people and places we love most.
While we’re getting cozy, it’s also worth noting that the local real estate market is expected to stay steady heading into fall 2025. Nationally, prices may cool slightly and inventory is expected to remain tight, but in Manitoba, activity remains healthy thanks to balanced supply, solid demand, and continued confidence in the market. So whether you're in your forever home or just enjoying the season, fall is still a great time to feel rooted where you are.
Here are 10 upcoming events that bring out the best of Winnipeg this September — each one authentic, memorable, and made for this time of year.
When: September 12 - 14
Enjoy live entertainment on our Fall Fair mainstage, the outdoor Pop-up Pub, a weekend-long Farmer's Market, food trucks, hay rides through the forest, carnival games, photo ops & more!
Bring the kids and enjoy the Kid's Activity Tent, children's entertainers on The Main Stage, barrel train, petting farm, bouncers, crafts and so much more!
Tickets are required for entry to Pineridge Hollow & The Village grounds Friday, September 12 -Sunday September 14. Tickets are $14 + tax for ages 2+, children under 2 years old are free. Weekend passes and bulk ticket pricing (5+ tickets) are available!
For more information and to purchase tickets, check them out here https://pineridgehollow.com/pages/fall-fair
When: Saturday, September 6th, 3 p.m.
Notable: The Blue Bombers are 8-1 in the last nine Banjo Bowl games, are on a five-game winning streak in the featured event and lead the overall series since its inception 13-7.
Can’t make it to the stadium? Bring the electrifying Rivalry Week home! Decorate in Blue & Gold, order your favorite stadium snacks, fire up the game broadcast on your screen, and let the cheers fill your living room.
Or maybe you want to watch the Bombers crush the Riders and sink your teeth into a Le Burger Week masterpiece—all from the comfort of your neighbourhood pub!
When: Sunday Sept 7, 12:00-5:00 p.m.
Classic cars glisten at the Red River Exhibition Park. It’s retro charm, engine roars, and community nostalgia rolled into one. With over 1000 vintage cars, food trucks, vendors, and live entertainment, free admission, $5 parking this could be the best way to enjoy your Sunday!
When: check the website daily for updates
https://www.cornmaze.ca/pages/hours-prices
Lose yourself in the corn maze, explore the petting zoo, climb the hay bale pyramid, or snap the perfect pics in the sunflower expo. It’s simple, seasonal fun just a short drive away.
When: Sept 20 - Oct 1 check website for details
https://thinairwinnipeg.ca/thin-air-festival/
Winnipeg International Writers Festival—THIN AIR (Late September)
For those who find warmth in words and stories, this week-long literary festival brings readings, conversations, and creativity to our community.
The Ultimutt Dog Party!
Raising the Woof! For Animal Rescue Groups
When: Sept 20&21 10:00 - 4:00 p.m.
Join fellow dog lovers and their furry friends for BarkFest; The Ultimutt Dog Party! September 20 & 21 at Exhibition Park, a weekend long festival of fun celebrating everything DOGS! Entertainment & Features include X-Treme Dogs Agility Performances, Doggy’s Got Talent Contest, Dapper Dogs Fashion Show, Zoomies Zone, Downward Dog Spaw, Scratch + Sniff Adventure, K9 Cafe, Eats + Treats Food Trucks, plus Barks + Brews Tent & Whine + Muttini Bar! Fun for the whole family includes Pawcasso Arts + Crafts Centre, Barkery Cookie Decorating, Puparazzi Selfie Wall, Mascot Meet + Greets, plus bouncers & games in the Kids Fun Zone.
BarkFest is proud to support K9 Advocacy Manitoba, Manitoba Mutts Dog Rescue Inc. & Manitoba Underdogs Rescue with our Raising the Woof! fundraising initiative, plus love & support for many other Local Animal Rescue Groups.
When: Sept 20&21 12:00-9:00 pm
Get ready for Live, Love Downtown — a vibrant festival that brings together local food, music, art, and community spirit. This event will shine a spotlight on the amazing people, nonprofits, and small businesses that make our city centre so special.
Live, Love Downtown is a dynamic, family-friendly event designed to revitalize and celebrate our city’s core!
Let’s keep the energy alive — and celebrate downtown like never before!
Location - Memorial Drive
https://www.facebook.com/events/582196568269241/582196574935907/?event_time_id=582196574935907
A damn good excuse to swirl, sip, and show off your "I know my sauvignon from my syrah" swagger.
When: Sept 26&27 RBC Convention Centre
https://somanitoba.akaraisin.com/ui/wwf2025/ticketing
The Public Tastings are the heart of the Winnipeg Wine Festival, featuring a wide selection of wines for you to taste. Your ticket includes admission, a souvenir tasting glass and 3 hours of sampling on the tasting floor. Whether you're discovering new wines or returning to your favourites, you won't want to miss out on this incredible event. Festival-goers who fall in love with a particular wine can even purchase it on the spot at the onsite Manitoba Liquor Mart.
When: Sat, Sept 6 6:00-9:00 p.m.
The 40th edition of the wildly successful stand-up comedy showcase. Six of Winnipeg’s best comedians perform their A material. No theme, no gimmicks, just top-notch comedy from Winnipeg’s funniest people. Featuring Jordan Welwood, Emmanuel Lomuro, Tyler Kotowski, Jaydin Pommer, Milan Horanski and Brady Holm. Hosted as always by Jared Story.
For tickets, click here https://www.ticketweb.ca/event/winnipeg-comedy-showcase-40-the-park-theatre-tickets/14369693?pl=TPT&REFID=clientsitewp
When: September 20 10:00-1:00 p.m.
register here - https://www.eventbrite.ca/e/artride-cool-gardens-and-public-art-tickets-1458804366129
Join StorefrontMB, the Winnipeg Arts Council, Winnipeg Public Art , and Bike Winnipeg ) for a guided bike tour showcasing public art across the city, featuring stops at all of this year’s Cool Gardens installations!The tour will start at Agassiz Ice in Assiniboine Park, and end at La Maison des Artistes sculpture garden in St. Boniface.
From spirited sports rivalries and canine celebrations to immersive art and indie zines, September’s highlights in Winnipeg remind us what makes our city feel like home. Whether you're out with family or wandering solo, these events are proof that magic happens in everyday community moments.
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