10 awesome things to do in and around Calgary this week (May 25-29)

It finally feels like we’re getting a little taste of summer in Calgary this week, and the events around the city are matching that energy. Think rooftop parties, comedy nights, outdoor sports games, and so much more.

We’ve rounded up 10 of our favourites so you don’t have to spend time searching for plans.

Without further ado, let’s get into it.

If your week could use a laugh, comedian Dave Nystrom is bringing his stand-up show to the city. Between his chaotic dad stories, quick humour, and completely unserious energy, it’s the kind of show where you’ll probably leave with a stomach ache from laughing too hard.

When: Monday, May 25, 2026
Time: 7 p.m. to 10 p.m.
Where: The Comedy Cave – 1020 8th Ave. SW, Calgary, Alta.
Cost: Starting at $16.92

If your idea of a perfect night out involves wine and cheese, the VIN Room West has you covered. They’re hosting a tasting experience with Peasant Cheese shop that brings together pours and pairings for a fun, laid-back evening.

When: Tuesday, May 26, 2026
Time: 6 p.m. to 7:30 p.m.
Where: Vin Room West – 8561 8A Ave. SW, Calgary, Alta
Cost: $75

Corb Lund is taking the stage at Ranchmans with a set focused on Cabin Fever and Horse Soldier! Horse Soldier! You can expect a mix of dry humour and that classic Alberta sound he’s known for.

When: Wednesday, May 27, 2026
Time: 8 p.m. to 2 a.m.
Where: Ranchmans – 9615 Macleod Trail SE, Calgary, Alta.
Cost: Starting at $51.52

The FunnyFest Comedy Competition is back for its 26th year, bringing a packed lineup of shows, workshops, and performances across the city.

With dozens of comedians and a mix of different themes, it’s basically a full-on celebration of every kind of humour you can think of.

When: Thursday, May 28 to June 7, 2026
Time: Performance times vary
Where: Various venues
Cost: Starting at $12.50

Catch the Calgary Surge as they compete against the Scarborough Shooting Stars in their first home game of the season.

When: Thursday, May 28, 2026
Time: 7:30 p.m.
Where: Winsport Event Centre – 88 Canada Olympic Rd. SW, Calgary, Alta.
Cost: Starting at $34

Beginning May 29, the Calgary Latin American Film Festival will showcase three days of contemporary Latin American cinema across independent theatres in Calgary.

When: Friday, May 29, 2026
Time: 6:15 p.m. to 9 p.m.
Where: Canyon Meadows Cinema – 13226 Macleod Trl. SW, Calgary, Alta.
Cost: Starting at $9.93

The Lougheed House is kicking off summer with a DJ party, silent auction, and plenty of chances to “party with a purpose.”

When: Friday, May 29, 2026
Time: 5 p.m. to 8 p.m.
Where: Lougheed House – 707 13th Ave. SW, Calgary, Alta.
Cost: $60 per person

If you’re all about shopping local, the YYC Fine Art Show is worth a stop. Throughout the space, you can expect handmade art, jewelry, and ceramics, all created by Calgary artists.

When: Friday, May 29, 2026, to Sunday, May 31, 2026
Time: 6 p.m. to 8 p.m.
Where: Strathcona Community Centre – 277 Strathcona Dr. SW, Calgary, Alta.
Cost: Free

A rooftop party with a purpose is coming to downtown Calgary as the Safe Haven Foundation celebrates 30 years of impact. Guests can expect city views, cocktails, music, and a night dedicated to celebrating and supporting young women in the community.

When: Friday, May 29, 2026
Time: 6 p.m. to 11 p.m.
Where: Calgary Marriott Downtown Hotel – 110 9th Ave. SE, Calgary, Alta.
Cost: Starting at $249

Baseball season is officially back, and the Okotoks Dawgs are stepping up to the plate for opening night. Expect a packed crowd, lots of energy, and that perfect small-town ballpark feel.

When: Friday, May 29, 2026
Time: 7:05 p.m.
Where: 256 Don Seaman Way, Okotoks, Alta.
Cost: Starting at $15

Enjoy your week, Calgary!

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