Weekend Family Events – June 27–28, 2026

Looking for something fun to do with the family this weekend? Here are 6 things happening in and around Calgary — and this week, we're celebrating the arts!

🎨 Chalk the Block – Montgomery Street Festival

Date: Saturday June 27 | 1:00 PM – 7:00 PM
Cost: Free
Montgomery's street festival turns the whole neighbourhood into a giant open-air gallery! Families can grab chalk and create sidewalk masterpieces right alongside professional artists working on breathtaking 3D pieces. With live entertainment, local artisan vendors, and a Brewsmith Brewing beer garden, it's one of NW Calgary's most creative community days. Cash prizes are awarded to chalk artists across all age categories.
📍 Bowness Rd NW between 44th & 46th Streets

🎶 JazzYYC JazzWalk – Tomkins Park Gazebo

Date: Sunday June 28 | 11:00 AM – 6:00 PM
Cost: Free
Close out JazzYYC's week-long Summer Festival with a full day of live jazz at Tomkins Park Gazebo in East Village. This free, family-friendly outdoor showcase is the perfect Sunday outing — lay a blanket on the grass, let little ones run around, and enjoy world-class music under the summer sky. No tickets, no fuss, just great jazz.
📍 Tomkins Park Gazebo, East Village

📚 Ultimate Summer Party – Central Library

Date: Saturday June 27 | 12:00 PM – 3:00 PM
Cost: Free
Calgary Public Library kicks off its Ultimate Summer Challenge with a free all-ages party at the Central Library! Enjoy interactive storytimes, a kids' dance party, tasty snacks, and hands-on summer crafts. Sign your child up for the summer reading challenge and get a free library card on the spot — the best free summer tradition in the city.
📍 Central Library, Shaikh Family Welcome Gallery, 800 3 St SE

🏰 High River Medieval Faire & Tournament

Dates: Saturday–Sunday June 27–28 | 10:00 AM – 5:00 PM
Cost: Adult $15 · Child (5–12) $10 · Senior $10 · Under 5 free
A full two-day medieval spectacle 45 minutes south of Calgary! Watch armoured knights clash in heavy combat, cheer on jousters thundering past the grandstand, and browse an artisan market packed with handcrafted goods. Costumes and capes are absolutely encouraged — this is one of those days the kids will talk about for weeks.
📍 High River Rodeo Grounds, High River, AB

🎪 Deerpoint Community Festival – 12th Annual

Date: Sunday June 28 | 10:00 AM – 3:00 PM
Cost: Free
The 12th Annual Deerpoint Community Festival brings together Deer Ridge, Deer Run, Queensland, and Parkland for a free outdoor celebration. Enjoy live music and dancing, local food and vendors, games, bouncy castles, and free giveaways — a beloved SE Calgary summer tradition that keeps getting better.
📍 Deer Point Plaza, 14919 Deer Ridge Dr SE

🎶 Country Thunder Alberta 2026

Dates: Fri June 26 – Sun June 28 | Fri 1:30 PM · Sat 12:00 PM · Sun 1:00 PM
Cost: Kids 10 & under free (GA) · Adult GA from $342 (3-day)
Calgary's biggest country music festival returns to The Confluence for three days of outdoor fun! Headliners Lainey Wilson, Kane Brown, and Tyler Hubbard take the riverside stage. Dust off your cowboy boots, explore the food truck village, and soak up the summer sun. Children 10 and under get in free in General Admission areas with a ticketed adult.
📍 The Confluence Historic Site & Parkland, 750 9 Ave SE

Have a great weekend, Calgary families! ☀️