![28th Jul: Masha and the Bear (2025), 3 Seasons [TV-Y] – New Episodes (6.6/10)](https://occ-0-171-92.1.nflxso.net/dnm/api/v6/0Qzqdxw-HG1AiOKLWWPsFOUDA2E/AAAABWVh724ToqMsafYzdNai1xe7oZNva-wjNxx7PIP7Ci5yZPwW4FkoA8G2L1H_KSs1PpeuobhFeFRLn-pn_8mqmrZGH_Wc3vLN0evLT58ffSLM_Q-pBNY6-Wv_Dl_fyp3HtuU8x22G-Vszeux56dPaR33wRPxYtM21KYEpK3Hc.jpg?r=de4 "28th Jul: Masha and the Bear (2025), 3 Seasons [TV-Y] – New Episodes (6.6/10)")
WinSport is hosting its first-ever drive-in movie this August, and it comes with a pretty iconic connection to Calgary’s past. Guests can head to Canada Olympic Park for an outdoor screening of the Disney classic Cool Runnings, which is about as fitting as it gets.
The movie already has a special place in Calgary history thanks to its ties to the 1988 Winter Olympics, so watching it in the former Olympic venue feels like a pretty full-circle moment.
Here’s everything you need to know about WinSport’s upcoming drive-in movie.
What to know about WinSport’s drive-in movie
The location is a big part of what makes this movie night so unique. Canada Olympic Park, now operated by WinSport, played a major role during the 1988 Winter Olympics, hosting major events throughout the games, including bobsleigh, luge, and ski jumping.
Today, the landmark has become a year-round destination for outdoor activities and community events, and continues to welcome visitors long after the Olympics ended.
For those who haven’t seen the film yet, Cool Runnings follows four Jamaican athletes who decide to form the country’s first bobsled team and take on the unlikely challenge of competing at the Olympics.
The film’s connection to Calgary comes from the real-life team that competed in the 1988 Winter Olympics, which is what makes watching it at Canada Olympic Park such a fitting choice.
As for the drive-in experience itself, guests will be able to watch the movie on a giant outdoor screen from the comfort of their vehicles while tuning into an FM stereo channel for the audio. You’re also more than welcome to bring your own snacks and drinks to enjoy throughout the screening!
Tickets, timing, and details
The drive-in movie will take place on Thursday, Aug. 13, 2026, at WinSport’s west overflow parking lot at Canada Olympic Park. Guests can arrive starting at 7 p.m., with the movie scheduled to begin at 9 p.m., once the sun has gone down enough for everyone to see the screen.
Organizers recommend arriving early to get settled and find an ideal parking spot before the movie starts, and it’s important to note that the start time may be delayed up to 10 minutes to ensure the viewing experience is just right.
Instead of individual tickets, admission is based on a parking fee of $41.50 per vehicle. It’s important to keep in mind that vehicles can only have as many people inside as there are available seatbelts, and cars exceeding that amount will not be allowed into the event.
Guests are also asked to stay in their vehicles for the entire duration of the movie, as setting up chairs directly in front of cars can create a safety hazard.
So round up your crew, pack some snacks, and make your way over to Canada Olympic Park for a movie with a pretty unforgettable Calgary connection.
When: Thursday, Aug. 13, 2026
Time: Gates open at 9 p.m. (showtime at 9 p.m.)
Where: WinSport Event Centre – 88 Canada Olympic Rd. SW, Calgary, Alta.
Cost: $41.50 per vehicle
Recent posts:
A massive free block party is taking over this Vancouver street with over 30 murals and live DJs
This new Calgary festival is giving away $1,000 for the best cowboy look
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.
Read articles
