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September 26th to November 1st –Halloween Haunt
With the Halloween season around the corner, Canada’s Wonderland will be fully transformed for a terrifying Halloween celebration, where nothing is as it seems. Expect terrifying haunted mazes, sinister scare zones, exhilarating live shows, and specialty food & drink.
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Where: 1 Canada’s Wonderland Drive, Vaughan
When: September 26th to November 1st,
Admission: Priced. Tickets start at $55. Grab your tickets here
September 27th to November 1st – Pumpkins After Dark Milton
One of the biggest Halloween events in North America, Pumpkins After Dark Milton, returns this Fall to the Country Heritage Park from September 27th to November 1st – Just an hour drive from Toronto.
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At this unique and family-friendly experience, guests will embark on a 1km outdoor walkthrough where over 10,000 hand-carved jack-o’-lanterns come to life after dark! There will be immersive displays, music, and plenty of nostalgic Halloween charm.
Where: 8560 Tremaine Rd, Milton
When: September 27th to November 1st
Admission: Priced. Tickets start at $23. Grab your tickets here
October 2nd to 5th – Markham Fair
Canada’s largest 4-day agricultural fair returns this October with midway shows, family-friendly activities, competitions, and fun.
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Where: Markham Fairgrounds, 10801 McCowan Rd, Markham
When: October 2nd to 5th
Admission: Priced. Tickets start at $10. Grab your tickets here
October 3rd – Bryan Adams
Canadian Singer Bryan Adams performs at the Scotiabank Arena this October
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Where: Scotiabank Arena
When: October 3rd, 8:00 pm
Admission: Priced. Tickets start at $161. Grab your tickets here
October 3rd to 5th – MAC Cosmetics Studio Pop-Up
Stop by the MAC Studio Pop-up for a complimentary shade matching by a MAC Artist. Plus, enjoy sweet treats, photo moments, and play to win exclusive MAC merch and available prizes. From soft-matte to radiant glow, MAC has got you covered!
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Where: The Well, Toronto
When: October 3rd to 5th, 11:00 am – 7:00 pm
Admission: Free
October 3rd to 5th – F45 HYROX TORONTO
Get set for a HYROX weekend like no other —HYROX TORONTO brings the heat back to Canada with an epic three-day fitness experience from October 3rd to 5th!
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Where: Enercare Centre, 100 Princes’ Blvd #1, Toronto
When: October 3rd to 5th,
Admission: Priced. Grab your tickets here.
October 3rd and 4th – The Chicken Cartel x Tondou Ramen Collaboration
Join The Chicken Cartel x Tondou Ramen for an exclusive collaboration between The Chicken Cartel by Chef Donnie Gomes and Tondou Ramen by Chef Kota Uechi. Together, they’ve crafted The Okinawa, a limited-edition chicken sandwich that layers crispy chicken breast glazed in Nanban sauce with Okinawa soba noodles, a soy-marinated egg (Nitamago), spicy sprouts, and a rich Taru Taru mayo all on a toasted brioche bun. To sip alongside, a house-made Tondou Lemonade of course!
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Where: Tondou Ramen, 596 College Street, Toronto
When: October 3rd and 4th,
Admission: Priced. Tickets start at $19. Grab your tickets here.
October 4th – Nuit Blanche
Nuit Blanche is a free all-night celebration of contemporary art that transforms Toronto’s public spaces into unexpected landscapes and animates cultural sites throughout the city.
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Where: Various Locations in Toronto
When: October 4th, 7:00 pm – 7:00 am
Admission: Free
October 4th – MANÁ
Acclaimed Mexican Band, MANÁ, performs at the Scotiabank Arena this October
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Where: Scotiabank Arena
When: October 4th, 8:00 pm
Admission: Priced. Tickets start at $69. Grab your tickets here
October 4th – The Art of the Blade
Meet Masashi Yamamoto, one of Japan’s greatest knife makers, and see him forge knives in Toronto! Known for his distinct, slick blades, world-class craftsmanship, and blazingly sharp edges, Masashi-san is one of the most skilled blacksmiths of our time. He’ll also be custom-engraving his knives for folks on-site!
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Where: 517 Bloor Street West, Toronto
When: October 4th, 11:30 am – 5:30 pm
Admission: Free. Register here
October 4th and 5th – Water/Fall Festival
Presented by The Waterfront BIA, the free-to-attend, fall-inspired arts and cultural festival will transform Toronto’s waterfront into a cultural hub providing visitors with spectacular public art installations (on and off the water), harvest-themed food & drink markets, live music and dance performances, a sustainable makers market, illuminating boat tours, and more.
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Where: Queens Quay, from Bathurst St. to Bay St.
When: October 4th and 5th
Admission: Free
October 4th and 5th – All Things Go Toronto
All Things Go is coming to Toronto for the first time — bringing together 16 artists shaping the next generation of music and culture for the best weekend of the year. Renee Repp headlines!
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Where: Budweiser Stage, Toronto
When: October 4th and 5th, 12:30 pm – 7:00 am
Admission: Priced. Tickets start at $190. Grab your tickets here
October 4th to November 1st – Legends of Horror at Casa Loma
This October, the grounds of Casa Loma will be transformed into an immersive theatrical experience, Legends of Horror. Done in the presentational form considered “promenade theatre”, in which the audience walks at their own pace through a 2 km trail commencing in the lower gardens of Casa Loma and winding its way through the castle’s tunnels and darkest spaces never before open to the public.
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Where: Casa Loma, Toronto
When: October 4th to November 1st,
Admission: Priced. Tickets start at $45. Grab your tickets here
October 5th – CIBC RUN FOR THE CURE
Join the Toronto community to race in support of all Canadians impacted by breast cancer.
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Where: University of Toronto, 27 King’s College Circle, Toronto
When: October 5th, 8:00 am – 12:00 pm
Admission: Register here.
October 5th and 6th – Roadmap to Billions Toronto Conference 2025
After its incredible debut last year, Roadmap to Billions Toronto 2025 returns for its second edition on October 5th and 6th, offering two unforgettable days of connections, community, and conversations with leading entrepreneurs and investors, as well as powerful workshops and dynamic networking experiences.
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Where: Downtown, Toronto
When: October 5th and 6th
- October 5th, TBA
- October 6th, 9:00 am – 6:00 pm
Admission: Priced. Tickets start at $200. Grab your tickets here
October 7th – Battle at THE HALL
Toronto’s most electrifying dance event is back — this time indoors at The Great Hall, offering an intriguing showcase of Hip-Hop, House, and Waacking, featuring some of the city’s most dynamic performers.
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Where: The Great Hall, 1087 Queen Street West, Toronto
When: October 7th, 6:00 pm – 10:00 pm
Admission: Priced. Tickets start at $22. Grab your tickets here
October 7th to 9th – Elevate Festival
Elevate Festival is a 3-day Tech and Innovation Festival in Canada that unites world-class innovators, industry leaders, and the tech ecosystem to shine a global spotlight on Canada’s tech and innovation ecosystem. It features world-class speakers, cutting-edge programming, networking opportunities, evening socials, and investor and startup events woven throughout.
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Where: Various Locations in Toronto
When: October 7th to 9th
Admission: Priced. Tickets start at $550. Grab your tickets here
October 8th – Beyond the Suit Toronto
Dress for Success Toronto will host its annual signature fundraising event, Beyond the Suit, on Wednesday, October 8th, 2025, at CIBC Square (81 Bay Street, Toronto). This inspiring evening brings together community leaders, professionals, and supporters to celebrate women and raise vital funds for programs that help women achieve growth and economic independence.
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Where: CIBC Square, 81 Bay Street, Toronto
When: October 8th, 6:00 pm – 9:00 pm
Admission: Priced. Tickets start at $125. Grab your tickets here
October 9th – Ice Cube
American Rapper Ice Cube performs at the Scotiabank Arena this October
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Where: Scotiabank Arena
When: October 9th, 8:00 pm
Admission: Priced. Tickets start at $84. Grab your tickets here
October 10th to November 1st – Screemers
Screemers is a Halloween spectacle featuring seven haunted walkthrough mazes, each with over 120 live actors, all under a massive 15,000 sq ft tent. The tent is packed with eerie props, captivating stage shows, and plenty of entertainment.
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Where: 80 Interchange Way, Vaughan
When: October 10th to November 1st
Admission: Priced. Tickets start at $39. Grab your tickets here
October 10th to 13th – Pumpkinfest
PumpkinFest Toronto, an epic pumpkin extravaganza, returns to Downsview Park from October 10th to 13th, featuring unlimited midway rides, inflatables, bounce houses, fun carnival games, and tasty local food trucks.
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Where: Downsview Park, Toronto.
When: October 10th to 13th, 10:00 am – 6:00 pm
Admission: Priced. Tickets start at $30. Grab your tickets here
October 10th to 12th – North York Diwali Fest: Festival of Lights 2025
NYDF (Festival of Lights) is a vibrant celebration of lights, music, food, and culture, uniting communities to experience the joy of Diwali, the largest Indian festival. This free public event showcases the rich heritage of South Asia through live performances, artistic showcases, interactive workshops, and a bustling marketplace.
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Where: Mel Lastman Square, Toronto
When: October 10th to 12th,
Admission: Free
October 11th to 13th – Woodbridge Fall Fair
The Woodbridge Fall Fair offers three days filled with fun and activities for the whole family. There will be live music, fair food, midway & games, and lots of fun stuff to do
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Where: 100 Porter Avenue., Woodbridge
When: October 11th to 13th,
Admission: Priced. Tickets start at $15. Grab your tickets here
October 12th – Adam Sandler
American Comedian, Adam Sandler, brings the laughs to the Scotiabank Arena this October
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Where: Scotiabank Arena
When: October 12th, 7:30 pm
Admission: Priced. Tickets start at $95. Grab your tickets here
October 14th to 19th – Female Eye Film Festival
Female Eye Film Festival is a competitive international women’s film festival showcasing films from women from across North America and the World
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Where: Various Locations in Toronto
When: October 14th to 19th
Admission: Priced. Grab your tickets here.
October 15th to 19th – Toronto After Dark Festival
Toronto After Dark presents 5 Nights of Horror, Sci-Fi, Action, and Cult Cinema in Toronto. This year’s version will feature 40 notable new films, including both feature-length and short films.
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Where: Scotiabank Theatre, 259 Richmond St. W
When: October 15th to 19th
Admission: Priced. Grab your tickets here.
October 15th to 26th – Fall for Dance North Festival
Fall for Dance North Festival (FFDN) returns for its 11th annual season, featuring more than 30 Canadian and international artists across multiple free and ticketed dance programs
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Where: Bluma Appel Theatre, 27 Front St E, Toronto
When: October 15th to 26th
Admission: Priced. Grab your tickets here.
October 16th to 19th, 24th to 26th – The Great Pumpkin Trail
The Great Pumpkin Trail returns to RBG! Follow the candlelit glow of hundreds of jack-o-lanterns deep within the recesses of the Hendrie Valley. Savor the flavors of the season with a selection of sweet and savory delights, while enjoying live entertainment and pumpkin-themed activities. New this Fall, 10,000 REAL pumpkins will be arranged in artistic displays and installations throughout Hendrie Park!
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Where: Hendrie Park (680 Plains Rd. W. Burlington)
When: October 16th to 19th, 24th to 26th, 5:30 pm
Admission: Priced. Tickets start at $32. Grab your tickets here
October 17th – Doechii
American Rapper Doechii performs in Toronto this October
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Where: Coca-Cola Coliseum, Toronto
When: October 17th, 8:00 pm
Admission: Priced. Tickets start at $93. Grab your tickets here
October 17th and 18th – Whisky Global Toronto
Explore and savour premium whiskies, uncovering their uniqueness at the iconic Heritage Court at Toronto’s Whisky Festival.
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Where: Heritage Court, Exhibition Place, Toronto
When: October 18th and 19th
Admission: Priced. Tickets start at $124. Grab your tickets here
October 18th – Toronto Sauna Festival
Presented in collaboration with Unbounded and Evergreen Brick Works, the Toronto Sauna Festival provides a playground for the senses, featuring a full day of curated sauna experiences, DJs, live music, cold plunges, breathwork & yoga Sessions, interactive booths, and fun!
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Where: Evergreen Brick Works
When: October 18th, 1:00 pm – 11:00 pm
Admission: Priced. Tickets start at $49. Grab your tickets here
October 18th and 19th – Toronto Waterfront Marathon
The TCS Toronto Waterfront Marathon is Canada’s premier running event and the grand finale of the Canada Running Series.
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Where: Yonge St. to Bay St, Toronto
When: October 18th and 19th
October 18th and 19th – Taste the Caribbean Culture and Market Hub
‘Taste the Caribbean Culture & Market Hub: A Pop-up Experience‘ is a 2-day event in Little Jamaica, offering a series of workshops, culinary demos, fireside chats, game tutorials, a pop-up market, complimentary tasting stations, a photo station, and live music.
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Where: Little Jamaica, 1553 Eglinton Avenue West
When: October 18th and 19th, 10:00 am – 7:00 pm
Admission: Free
October 19th and 20th – Laufey
Pop artist Laufey performs at Scotiabank Arena this October
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Where: Scotiabank Arena
When: October 19th and 20th, 7:30 pm
Admission: Priced. Tickets start at $141. Grab your tickets here
October 23rd to 25th – comedy is art 2025
Comedy is Art 2025 provides three nights of comedy, featuring over 20 comics from across Toronto and beyond. The lineup includes shows such as Andrew Phung and Friends, Not Hamilton Improvised, Nkasi Ogbonnah’s Afronaut, and more. Additionally, a serious day of comedy is offered with Bad Dog Theatre.
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Where: Various Locations in Toronto
When: October 23rd to 25th,
Admission: Priced. Grab your tickets here.
October 24th – GALA OF COCKTAILS
Presented by the Alchemist, The Gala of Cocktails is the largest and most celebratory event of the Toronto Cocktail Festival, featuring multi-award-winning bartenders, brand ambassadors, and chefs, as well as a diverse selection of food and cocktails. There will be 30 open bar stations, over 50 cocktails, great music, and lots of fun.
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Where: Waterworks Food Hall, 50 Brant Street, Toronto
When: October 19th and 20th, 7:00 pm – 11:00 pm
Admission: Priced. Tickets start at $158. Grab your tickets here
October 24th to 26th – Toronto Ski and Snowboard Show
The Toronto Ski and Snowboard Show showcases all things ski and snowboarding in Toronto. Discover cutting-edge gear, explore travel destinations, and snag deals from top retailers.
From ski and snowboard enthusiasts who can’t wait to hear about the latest winter trends, to people who want to learn how to ski and snowboard, and to families seeking the best deals on winter activities and gear, the show is ready to help people of all skill levels embrace winter.
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Where: 195 Princes’ Blvd, Toronto
When: October 24th to 26th
- October 24th, 3:00 pm – 9:00 pm
- October 25th, 10:00 am – 6:00 pm
- October 26th, 10:00 am – 5:00 pm
Admission: Priced. Tickets start at $12. Grab your tickets here
October 26th and 27th – Vybz Kartel
DanceHall King, Vybz Kartel, performs in Toronto this October
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Where: Scotiabank Arena
When: October 26th and 27th, 8:00 pm
Admission: Priced. Grab your tickets here.
October 27th – PinkPantheress
British Singer PinkPantheress performs at Massey Hall this October
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Where: Massey Hall
When: October 27th, 8:00 pm
Admission: Priced. Tickets start at $78. Grab your tickets here
October 31st – ROM AFTER Dark
ROM After Dark: Trick or Treat returns on October 31st! Get ready for a spine-tingling night filled with ghastly ghosts, pulsing live music, DJ sets, and non-stop dancing. Experience the Museum as it is transformed with eerie projections and larger-than-life inflatables that are guaranteed to give you goosebumps. Plus, each visitor gets a free drink ticket* and access to Sharks.
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Where: 100 Queens Park, Toronto
When: October 27th, 7:30 pm
Admission: Priced. Tickets start at $40. Grab your tickets here
October 31st and November 1st – Zamna Festival
Zamna Festival returns to Toronto this Halloween Weekend – October 31st & November 1st, 2025 – at The International Centre, providing a two-night odyssey of electronic music, bespoke stage design, otherworldly visual installations, and great sounds from artists all around the world.
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Where: The International Centre, Toronto
When: October 31st, 7:00 pm – 4:00 am
Admission: Priced. Tickets start at $109. Grab your tickets here