Upcoming Events in Owen Sound and Grey County: Winter-Spring 2026
Looking for things to do in Owen Sound and Grey County? Here is your complete guide to upcoming events for Winter and Spring 2026.
Roxy Theatre – Owen Sound
The historic Roxy Theatre is the regional centre for downtown Owen Sound and Grey County’s vibrant arts culture. The 400-seat theatre hosts concerts, comedy, and Owen Sound Little Theatre productions.
The Great Canadian Comedy Caravan Tour
Thursday, January 30, 2026 | 8:00 PM
A night of stand-up comedy featuring top Canadian comedians.
- Location: Roxy Theatre, 251 9th Street East, Owen Sound
- Tickets: Buy tickets
- Source: Roxy Theatre Events
Classic Seger – Bob Seger Tribute
Friday, January 31, 2026 | 7:30 PM
The legendary tribute to Bob Seger and The Silver Bullet Band brings the classic rock hits to life.
- Location: Roxy Theatre, Owen Sound
- Tickets: Buy tickets
- Source: Roxy Theatre Events
The Complete Works of William Shakespeare (abridged)[revised]
February 20, 21, 26-28, 2026 at 7:30 PM | February 22 at 2:00 PM
An Owen Sound Little Theatre Production. This fast-paced, witty and physical play features all 37 of Shakespeare’s plays performed in 97 minutes by 3 actors. Full of laughter for audiences of all ages.
- Location: Roxy Theatre, Owen Sound
- Tickets: Buy tickets
- Source: Roxy Theatre Events
Abbamania / Night Fever
Thursday, March 5, 2026 | 7:30 PM
A double tribute show celebrating the music of ABBA and the Bee Gees.
- Location: Roxy Theatre, Owen Sound
- Tickets: Buy tickets
- Source: Roxy Theatre Events
Leahy
Friday, March 6, 2026 | 7:30 PM
The legendary Canadian Celtic family band brings their high-energy fiddle-driven music to Owen Sound.
- Location: Roxy Theatre, Owen Sound
- Tickets: Buy tickets
- Source: Roxy Theatre Events
Paddling Film Festival
Friday, March 13, 2026 | 7:30 PM
World tour of paddling films featuring kayaking, canoeing, and SUP adventures from around the globe.
- Location: Roxy Theatre, Owen Sound
- Tickets: Buy tickets
- Source: Roxy Theatre Events
Hells Bells – AC/DC Tribute
Saturday, March 14, 2026 | 7:30 PM
Celebrating the music of AC/DC with all the classic rock anthems.
- Location: Roxy Theatre, Owen Sound
- Tickets: Buy tickets
- Source: Roxy Theatre Events
Grey County Events
Whiskey Jack – Stompin Tom Tribute
Thursday, February 5, 2026 | 7:30 PM
Connors Canada meets Cullens Comedy. Since Whiskey Jack’s Duncan Fremlin first shook hands with Stompin Tom Connors back in 1990, their musical partnership has delighted audiences across Canada.
- Tickets: $35
- Source: Visit Grey Events
Gowan 2026 Tour
Wednesday, February 11, 2026 | 7:30 PM
Celebrate an evening with Gowan, Scottish-born Canadian rock icon and current front man of Styx. Renowned for his platinum solo hits including A Criminal Mind and Strange Animal.
- Tickets: $130
- Source: Visit Grey Events
West Grey Frazzlefest 2026
Friday, February 13 – Monday, February 16, 2026 (Family Day Weekend)
Get ready for the ultimate family weekend in West Grey. Join us at Family Day Frazzlefest for a lineup of events you will not want to miss. Bring the whole crew for a weekend packed with fun and activities.
- Location: West Grey
- Source: Visit Grey Events
Yuk Yuks Comedy Night – Valentines Day
Saturday, February 14, 2026 | 8:30 PM
Celebrate Valentines Day with laughter. Yuk Yuks Comedy Tour is coming to Cobble Beach – the perfect night out for couples, friends, or anyone who loves to laugh.
- Location: Cobble Beach
- Source: Visit Grey Events
Love is in the Air – Romantic Concert
Saturday, February 14, 2026 | 3:00 PM – 5:30 PM
Matt Chittick, Holly Chaplin, Katy Clark, and Johnathon Kirby present an afternoon of romantic music. Bring your valentine and swoon over some of the greatest love songs.
- Source: Visit Grey Events
Tom Thomson Art Gallery
Harold Klunder: The Dance of Life
January 24 – April 18, 2026
A major exhibition featuring works by renowned Canadian artist Harold Klunder.
Forecast
January 24 – June 20, 2026
Contemporary exhibition exploring themes of environment and climate.
- Location: Tom Thomson Art Gallery, 840 1st Ave W, Owen Sound
- Admission: By donation
- Source: Tom Thomson Art Gallery
Coming Up – Spring 2026
More great events at the Roxy Theatre:
- April 16-25: Witness For The Prosecution – Tickets
- April 29: Ian Thomas – Not Gone Yet! – Tickets
- April 30: Dreamer (Supertramp tribute) – Tickets
- May 1: Hotel California (Eagles tribute) – Tickets
- May 22-30: Shrek the Musical JR – Tickets
- June 5: Becoming the Beatles – Tickets
- June 6: 80s Confidential – Tickets
- June 12: The HiP Machine (Tragically Hip tribute) – Tickets
- June 13: Fleetwood Mac Mania – Tickets
- June 20: We Walk The Line (Johnny Cash tribute) – Tickets
Living in Owen Sound and Grey County
Owen Sound offers a delightfully social lifestyle with strong local community spirit. Located on the southern shores of Georgian Bay and just one hour south of Bruce Peninsula National Park, it is the perfect blend of natural beauty and cultural attractions.
Thinking of making Grey County your home? The Egan Team can help you explore real estate opportunities in Owen Sound and surrounding areas. Contact us to start your real estate journey.
Phone: 416-400-2800 | Website: www.patrickegan.com
Event Sources
Event information compiled from official sources:
Photos: Unsplash. Please verify event details with organizers before attending.
