October is here, which means Calgary is officially entering spooky season! The leaves are changing, pumpkins are popping up around the city, and Halloween events are starting up again. But if you’re not quite ready to spend your entire weekend surrounded by ghosts and pumpkins, don’t worry; there are comedy shows, live theatre events, festivals, and plenty of other things to check out around the city.
If you’re not sure what to add to your itinerary this weekend, we’ve rounded up some of the best things happening in and around the city, so you can skip the scrolling and start making plans.
Pumpkins After Dark is back at Winsport, turning the grounds into a giant walk-through display with thousands of hand-carved pumpkins. Alongside the giant gourds, there will be live carving demonstrations, roaming performers, and a haunted maze to navigate.
When: Friday, Oct. 2 to Saturday, Oct. 31, 2026
Time: 6:30 to 11 p.m.
Where: WinSport – 88 Canada Olympic Rd. SW, Calgary, Alta.
Cost: Starting at $17.19
The StoryBook Theatre is putting a spin on the classic The Jungle Book with this original musical adaptation. Follow Mowgli as he grows up in the city and finds his way through a world filled with new characters, music, and adventure.
When: Friday, Oct. 2 to Saturday, Oct. 31, 2026
Time: Show times vary
Where: StoryBook Theatre – 375 Bermuda Dr., Calgary, Alta.
Cost: Starting at $28
Massive pumpkins are taking over Calgary Farmers’ Market this weekend for the Colossal Carve. You can watch professional carver Yann Blanchard work on giant pumpkins throughout the event, while kids can search for hidden golden gourds and decorate their own mini pumpkins. There’s also a pumpkin-weight guessing contest, live music, and plenty of cute fall photo ops.
When: Saturday, Oct. 3 (West location), Sunday, Oct. 4 (South location)
Time: 11 a.m. to 3 p.m.
Where: Calgary Farmers’ Market West — 25 Greenbriar Dr. NW, Calgary, Alta., Calgary Farmers’ Market South — 510 77th Ave. SE, Calgary, Alta.
Cost: Free
The Calgary Zoo is getting a mysterious makeover for ZooDunnit, an adults-only murder mystery where you’ll follow clues, question suspects and try to figure out whodunnit. Along the way, you can explore the zoo after hours, enjoy live entertainment and see if you can solve the case before the night is over.
When: Friday, Oct. 2, 2026
Time: 5 p.m.
Where: Calgary Zoo — 210 St. George’s Dr. NE, Calgary, Alta.
Cost: $94 plus GST
You know him from Impractical Jokers, but Sal Vulcano is stepping away from the challenges and pranks for a night of stand-up at Macewan Hall. Expect an evening of stories, jokes, and plenty of personal material as he takes the stage on his own.
When: Friday, Oct. 2, 2026
Time: 7 to 11:30 p.m.
Where: Macewan Hall — 2500 University Dr. NW, Calgary, Alta.
Cost: Starting at $60.73
Butterfield Acres is kicking off fall with its Harvest Pumpkin Fest, where you can spend the day visiting the farm animals and taking part in fall activities around the property. There will also be wagon rides, pumpkin hunts, pumpkin decorating, and more.
When: Saturday, Oct. 3, and Sunday, Oct. 4, 2026
Time: 10 a.m. to 4 p.m.
Where: Butterfield Acres — 254077 Rocky Ridge Rd. NW, Calgary, Alta.
Cost: Children: $16.99 plus GST, Adults: $19.99 plus GST
This 16+ walking tour takes you through downtown Calgary, where a guide shares stories about some of the city’s historic crimes. You’ll learn about real homicides and criminal cases connected to the places you’ll visit along the route.
When: Saturday, Oct. 3, 2026
Time: 2 to 3 p.m.
Where: The Confluence — 750 9th Ave. SE, Calgary, Alta.
Cost: $20 plus fees
Couple’s Clownselling is a comedy show that turns relationship problems into an interactive night of laughs. The night will feature comedians and clowns tackling a series of real-life relationship scenarios and include plenty of audience participation.
When: Saturday, Oct. 3, 2026
Time: 7 to 8:30 p.m.
Where: Vern’s — 622 8th Ave. SW, Calgary, Alta.
Cost: Starting at $28.07
The Calgary Philharmonic is putting Beyoncé hits like “Crazy in Love,” “Single Ladies,” and Texas Hold ‘Em” alongside Beethoven’s Seventh Symphony at the Jack Singer Concert Hall. Conductor and Creator Steve Hackman has arranged the two styles together, with three vocalists joining the orchestra for the performance.
When: Saturday, Oct. 3, 2026
Time: 7:30 p.m.
Where: Jack Singer Concert Hall — 225 8th Ave. SE, Calgary, Alta.
Cost: Starting at $35
The CIBC Run for the Cure is back in Calgary this weekend, bringing locals together for a 5 km run or walk in support of breast cancer research and support programs. You can take part with friends, family or on your own, and the event will also feature music, activities and a community celebration before and after the route.
When: Sunday, Oct. 4, 2026
Time: 7 a.m. to 10 a.m.
Where: Southcentre Mall — 100 Anderson Rd. SE, Calgary, Alta.
Cost: $2 registration fee
Enjoy the weekend!
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Kaiya Williams
Kaiya is a Calgary-based writer and content creator with a background in marketing and digital storytelling. She has a passion for community-driven stories and covering local experiences that connect people.
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