Kingston Live Music & Events in May

May in Kingston starts to feel like the city stretching after a long winter—patios waking up, guitars drifting through open doors, and music spilling into the streets like sunlight you didn’t realize you missed. From laid-back Sunday sessions and intimate songwriter nights to full-blown festivals, tribute shows, comedy, and everything in between, this month is stacked with reasons to get out of the house. Whether you’re chasing that perfect live band moment, discovering a new local artist, or just looking for a good excuse to stay out a little longer, May delivers in every direction.

And the best part? This list keeps growing. New shows, last-minute additions, and hidden gems pop up all the time, so make it a habit to check back every Thursday for updates. Don’t let routine win the weekend—grab a friend, follow the sound, and let Kingston’s music scene do what it does best… fill you up.

May 3rd – Sunday Funday: Chicken Pickin’ @ The Cove Inn – 13:00-16:00
May 3rd – Sundays with Sierra: Vincenzo Stabile @ La Vida Bistrobar and Social – 13:30-16:30
May 3rd – Into the Dreaming: Kingston Choral Society @ The Spire – 14:30-16:30
May 3rd – Marion Drexler Band @ Time Out Bar & Bistro – 15:00-17:30
May 3rd – Shaun Kirk @ Monte’s – 18:30-20:30
May 3rd – Open Mic: Steve Giberson @ Time Out Bar & Bistro – 19:00-22:00
May 3rd – Live Band Karaoke @ The Merchant Tap House – 21:00-00:00
May 4th – Jazz Society Jam @ The Club at the R.C.H.A. – 16:30-18:30
May 4th – Monday Musical Residency: Jonathan Jones @ The Cove Inn – 17:00-20:00
May 5th – Tom’s TuNesday Afternoon Happy Hour Jam: Tom Savage @ The Club at the R.C.H.A. – 16:00-19:00
May 5th – Eric Uren, Meghan Balogh @ The Cove Inn – 17:00-20:00
May 5th – Traditional Irish Seisiún @ The Toucan – 19:30-22:00
May 6th – 2026 Bader & Overton Canadian Piano Competition @ Isabel Bader Centre – 12:30-17:00
May 6th – Buzz Hummer @ The Bank Gastrobar – 17:30-19:30
May 6th – Wings ’n Tunes: Shawn McCullough @ The Cove Inn – 17:00-20:00
May 6th – Re-Scheduled – Hollow Body @ Hotel Wolfe Island – 18:30-19:30
May 6th – Karaoke @ Time Out Bar & Bistro – 18:00-21:00
May 6th – The Day the Internet Died @ Sydenham High School – 19:00-21:00
May 6th – ReelOut Fundraiser: The Comedy of Errors @ Domino Theatre – 19:30-22:00
May 6th – Re-Scheduled – The Hotel Sessions: Open Mic Night @ Hotel Wolfe Island – 19:30-22:30
May 6th – Cancelled – Open Stage Drag Show: Rowena Whey @ The Grad Club – 20:00-22:30
May 7th – 2026 Bader & Overton Canadian Piano Competition @ Isabel Bader Centre – 12:30-18:00
May 7th – Original Thursdays: Lauren Carson @ The Cove Inn – 17:00-20:00
May 7th – Cancelled – Blues at The Cove: David Rotundo Does Dylan @ The Cove Inn – 17:00-20:00
May 7th – Clear Breeze @ Hotel Wolfe Island – 18:00-21:00
May 7th – Chris Murphy @ The Club at the R.C.H.A. – 19:00-21:30
May 7th – Half Moon Run @ The Spire – 19:00-21:30
May 7th – The Day the Internet Died @ Sydenham High School – 19:00-21:00
May 7th – The Spectators @ Time Out Bar & Bistro – 19:00-22:00
May 7th – The Comic Strippers @ Kingston Grand Theatre – 19:30-21:30
May 8th – The Beat Council: Willhound @ The Spire – 12:00-15:00
May 8th – Baroque Celebration Feast @ St. James’ Anglican Church – 17:15-19:00
May 8th – Field Trip @ The Cove Inn – 17:00-20:00
May 8th – Cancelled – Blues at The Cove: David Rotundo Band @ The Cove Inn – 19:00-23:00
May 8th – Lukas Oak @ The Loaf N’ Ale Pub & Restaurant – 19:00-21:00
May 8th – RetroKings @ Time Out Bar & Bistro – 19:00-22:00
May 8th – Sold Out – UK Calling @ The Broom Factory – 19:00-23:00
May 8th – Rob Moir, Tim Vantol @ Musiikki Café & Whiskey Bar – 19:30-22:00
May 8th – Ian Thomas… Not Gone Yet! @ Kingston Grand Theatre – 19:30-21:30
May 8th – Sit Down Series: The Salt Cellars @ Monte’s – 18:30-20:30
May 8th – Island Time – Afrobeats Edition: DJ Zari @ Hotel Wolfe Island – 20:00-00:00
May 8th – The Day the Internet Died @ Sydenham High School – 19:00-21:00
May 8th – The Oreoz @ The Merchant Tap House – 22:30-00:00
May 8th – Owl Farm, Gifts of Guilt @ The Toucan – 22:30-02:00
May 9th – Mage Tears, Ebril @ The Broom Factory – 12:15-14:30
May 9th – Blues at The Cove: Blackburn Brothers @ The Cove Inn – 19:00-23:00
May 9th – Andrew Mack Band @ The Embassy Live Music Café – 19:00-21:30
May 9th – Strung Out, Belvedere, Anchored Lines @ The Broom Factory – 19:30-22:30
May 9th – Cancelled – Outre-Tombe, Vrexiza @ The Grad Club – 20:00-22:30
May 9th – Chris Koster @ Hotel Wolfe Island – 20:00-22:30
May 9th – 2026 Bader & Overton Canadian Piano Competition @ Isabel Bader Centre – 12:30-18:00
May 9th – Haircuts and Cake-Walks: The Forgotten Black Minstrels of Kingston’s Musical Past @ Kingston Frontenac Public Library – 14:00-17:00
May 9th – Help CKP Record Their Album: The Celtic Kitchen Party @ Monte’s – 14:00-17:00
May 9th – J.S. Miller @ Time Out Bar & Bistro – 15:00-17:30
May 9th – Gerry Dee: Funny You Should Say That @ Kingston Grand Theatre – 19:00-21:30
May 9th – The Bowie Lives: A Bowie Spectacular @ The Spire – 19:30-22:30
May 9th – The Trevor Walsh Band @ Time Out Bar & Bistro – 20:00-23:00
May 9th – Plastic Paddy @ Tir Nan Óg – 21:00-00:00
May 9th – 3 Pistols @ The Merchant Tap House – 22:30-02:00
May 9th – Jelly Train @ The Toucan – 22:30-02:00
May 10th – Mother’s Day Tea @ Tett Centre for Creativity & Learning – 11:30-13:30
May 10th – Magic of Sibelius: Orchestra Kingston @ The Spire – 14:30-16:30
May 10th – Dave McGrath @ Time Out Bar & Bistro – 15:00-17:30
May 10th – Eric Uren, Meghan Balogh @ The Cove Inn – 17:00-20:00
May 10th – Open Mic: Steve Giberson @ Time Out Bar & Bistro – 19:00-22:00
May 10th – Live Band Karaoke @ The Merchant Tap House – 21:00-00:00
May 11th – Monday Musical Residency: Jonathan Jones @ The Cove Inn – 17:00-20:00
May 12th – Tom’s TuNesday Afternoon Happy Hour Jam: Tom Savage @ The Club at the R.C.H.A. – 16:00-19:00
May 12th – Eric Uren, Meghan Balogh @ The Cove Inn – 17:00-20:00
May 12th – Weird Nightmare @ The Broom Factory – 19:30-22:00
May 12th – Grand OnStage 2026-2027 Season Launch @ Kingston Grand Theatre – 19:30-21:30
May 12th – Traditional Irish Seisiún @ The Toucan – 19:30-22:00
May 13th – Sam Wood @ The Bank Gastrobar – 17:30-19:30
May 13th – Wings ’n Tunes: Shawn McCullough @ The Cove Inn – 17:00-20:00
May 13th – Karaoke @ Time Out Bar & Bistro – 18:00-21:00
May 13th – Ariel Posen, Wendlo @ Signal Brewery – 20:00-22:00
May 13th – Comedy Night: Sterling Scott, Al Babcock @ The Merchant Tap House – 20:00-22:00
May 13th – Bill Kirchen @ Hotel Wolfe Island – 20:30-22:00
May 14th – Year-End Concert “Joy!”: Sistema Kingston @ Isabel Bader Centre – 16:30-18:30
May 14th – Original Thursdays: Curtis Chaffey @ The Cove Inn – 17:00-20:00
May 14th – Drag Bingo @ Daft Brewing – 19:00-23:00
May 14th – Ted Lalonde @ Time Out Bar & Bistro – 19:00-22:00
May 14th – Comedy at The Creekside: Sterling Scott, Al Babcock @ The Creekside Bar & Grill – 19:00-21:00
May 14th – Efrim Menuck, One Leg One Eye @ The Broom Factory – 19:30-22:00
May 14th – Good Co., Mike Frazier, Fraser Wayne & The Desert Eagles @ The Buckle – 20:00-23:00
May 14th – Hellhound Trail @ Hotel Wolfe Island – 20:30-22:30
May 15th – Derek Meredith @ Time Out Bar & Bistro – 15:00-17:30
May 15th – Bosko Baker & The Do Makers @ The Cove Inn – 17:00-20:00
May 15th – Laine Raudsepp @ The Loaf N’ Ale Pub & Restaurant – 19:00-21:00
May 15th – Spencer Evans @ Time Out Bar & Bistro – 19:00-22:00
May 15th – Dallas Alexander, Nayana @ The Broom Factory – 19:00-22:00
May 15th – Music of Stranger Things Live by Candlelight @ The Spire – 19:00-21:00
May 15th – R-Banned @ Royal Canadian Legion Branch 560 – 19:00-23:00
May 15th – Beatlemania @ Kingston Grand Theatre – 19:30-21:30
May 15th – Guest Slippers Festival: The Silver Sardines, Liam Cole @ Private Residence – 20:00-22:00
May 15th – Mad Wet Sea, Noor, Hangman’s Graveyard @ Overtime Sports Bar – 20:00-23:00
May 15th – Carlo Muscat Quintet @ Hotel Wolfe Island – 20:00-21:30
May 15th – Andrew Vanhorn @ Tir Nan Óg – 21:00-00:00
May 15th – No Limits @ The Merchant Tap House – 22:30-00:00
May 15th – Ryan Ziggs & The Zaggs @ The Toucan – 22:30-02:00
May 16th – Guest Slippers Festival: Michael Antelope, Jenny, Jon & Michael @ Private Residence – 14:00-16:00
May 16th – RetroKings @ Spearhead Brewery – 14:00-17:00
May 16th – Guest Slippers Festival: TYΦA @ Private Residence – 17:00-19:00
May 16th – Ascension Blacklist, Single Wound, Exogen, No Small Affair, Rotweiler35 @ The Broom Factory – 18:00-22:30
May 16th – D-Shoots @ The Embassy Live Music Café – 19:00-21:30
May 16th – The Maduros @ Time Out Bar & Bistro – 19:00-22:00
May 16th – The New Moon Gallery Showcase: Vicki Brittle, The Family Name, Jarred Sine @ Medium Effort Fine Art Supplies – 19:30-23:00
May 16th – Moved, Note New Venue – The Creepshow, K-Man and the 45’s, Joystick!, Lumpfish, doingok @ Overtime Sports Bar – 19:30-23:00
May 16th – Guest Slippers Festival: Sabre Teeth, Hsien @ Private Residence – 20:00-22:00
May 16th – Hobby, Mistaken for Wayne, Emilie Steele & The Deal @ The Buckle Down – 20:30-00:30
May 16th – Album Launch: Suzanne Jarvie @ Hotel Wolfe Island – 20:30-22:30
May 16th – Dr. Bombay @ Tir Nan Óg – 21:00-00:00
May 16th – The Ice Gods @ The Merchant Tap House – 22:30-00:00
May 16th – ToneKats @ The Toucan – 22:30-02:00
May 17th – Ryan Gollogly @ Time Out Bar & Bistro – 15:00-17:30
May 17th – Eric Uren, Meghan Balogh @ The Cove Inn – 17:00-20:00
May 17th – Royal Tusk @ The Broom Factory – 19:30-22:00
May 17th – Open Mic: Steve Giberson @ Time Out Bar & Bistro – 19:00-22:00
May 17th – Live Band Karaoke @ The Merchant Tap House – 21:00-00:00
May 18th – Monday Musical Residency: Jonathan Jones @ The Cove Inn – 17:00-20:00
May 19th – Tom’s TuNesday Afternoon Happy Hour Jam: Tom Savage @ The Club at the R.C.H.A. – 16:00-19:00
May 19th – Eric Uren, Meghan Balogh @ The Cove Inn – 17:00-20:00
May 19th – Brother Elsey @ The Broom Factory – 19:30-22:00
May 19th – Quirks of Human Nature: Meg Freer, Deborah Schuurmans @ Time Out Bar & Bistro – 19:30-21:30
May 19th – Traditional Irish Seisiún @ The Toucan – 19:30-22:00
May 20th – Wings ’n Tunes: Shawn McCullough @ The Cove Inn – 17:00-20:00
May 20th – Karaoke @ Time Out Bar & Bistro – 18:00-21:00
May 20th – Cancelled – VERSE-ATILE Part 2 @ The Grad Club – 20:30-23:00
May 21st – Original Thursdays: Matthew Holtby @ The Cove Inn – 17:00-20:00
May 21st – Wayne Riley @ Time Out Bar & Bistro – 18:00-20:00
May 21st – Open Season: Hugh Christopher Brown, Joey Wright, Jason Mercer @ Hotel Wolfe Island – 19:00-21:00
May 21st – North of Nashville Songwriter Series @ Kingston Grand Theatre – 19:00-21:30
May 22nd – Krista Hartman @ The Cove Inn – 17:00-20:00
May 22nd – The Red Handed @ Time Out Bar & Bistro – 18:00-20:00
May 22nd – Whiskey Smoke @ The Loaf N’ Ale Pub & Restaurant – 19:00-21:00
May 22nd – Triple-J, Six Deep @ Spearhead Brewery – 19:00-22:00
May 22nd – The Shoop Shoop Show: The Cher Collection @ Kingston Grand Theatre – 19:00-21:30
May 22nd – Dave Gunning @ The Broom Factory – 19:30-22:00
May 22nd – Live French Chansons @ Martello Alley – 19:30-21:30
May 22nd – Mauricio & The Latin Beat Band @ The Spire – 19:30-21:30
May 22nd – Gerald McGrath @ Tir Nan Óg – 21:00-00:00
May 22nd – The Oreoz @ The Merchant Tap House – 22:30-00:00
May 22nd – Thunder Glove & The Great Octopus @ The Toucan – 22:30-02:00
May 23rd – EcoFest Westport: Nepean Panharmonic Steel Drum Band, The Rivermen, Anne Archer @ The Cove Inn – 10:00-22:00
May 23rd – Summer Kickoff Music Festival @ Centennial Park – 14:00-21:00
May 23rd – River City Junction @ The Cove Inn – 17:00-21:00
May 23rd – Doug van der Horden @ The Embassy Live Music Café – 19:00-21:30
May 23rd – Ten: Voices Rock Medicine Kingston, The Gertrudes @ Kingston Grand Theatre – 19:00-21:30
May 23rd – Tyler Brett Forkes @ The Social YGK – 19:00-21:00
May 23rd – Break The Night @ The Merchant Tap House – 22:30-00:00
May 23rd – Books & Brews: Bookish Market @ Spearhead Brewery – 14:00-19:00
May 23rd – RetroKings @ Spearhead Brewery – 14:00-17:00
May 23rd – Scott & Kate Live! @ Time Out Bar & Bistro – 19:00-22:00
May 23rd – A Tragically Hip Celebration: 50 Mission @ The Spire – 20:00-22:30
May 23rd – Summer Rock Your Face Off: Andrew Mack Band @ Tir Nan Óg – 21:00-00:00
May 23rd – Sweet Pete & The Heat @ The Toucan – 22:30-02:00
May 24th – Monster Spectacular 2026 @ Slush Puppie Place – 14:00-16:00
May 24th – Back Beat & Boogie @ Time Out Bar & Bistro – 16:00-18:00
May 24th – Eric Uren, Meghan Balogh @ The Cove Inn – 17:00-20:00
May 24th – Open Mic: Steve Giberson @ Time Out Bar & Bistro – 19:00-22:00
May 24th – Cat Clyde @ The Broom Factory – 19:30-22:00
May 24th – Live Band Karaoke @ The Merchant Tap House – 21:00-00:00
May 25th – Monday Musical Residency: Jonathan Jones @ The Cove Inn – 17:00-20:00
May 25th – Menopause The Musical 2 @ Kingston Grand Theatre – 19:30-21:30
May 25th – World Tour 2026: Kate Voegele, Tyler Hilton @ The Spire – 20:00-22:30
May 26th – Tom’s TuNesday Afternoon Happy Hour Jam: Tom Savage @ The Club at the R.C.H.A. – 16:00-19:00
May 26th – Eric Uren, Meghan Balogh @ The Cove Inn – 17:00-20:00
May 26th – Traditional Irish Seisiún @ The Toucan – 19:30-22:00
May 27th – Wings ’n Tunes: Shawn McCullough @ The Cove Inn – 17:00-20:00
May 27th – Karaoke @ Time Out Bar & Bistro – 18:00-21:00
May 27th – Choral Evensong: Capella Regalis Choirs, Paul Halley @ St. George’s Cathedral – 19:00-20:00
May 27th – The Hotel Sessions: Open Mic Night @ Hotel Wolfe Island – 19:30-22:30
May 27th – Gananoque Pride Alliance Presents: Legally Blonde @ 1000 Islands Drive-In – 20:30-22:30
May 28th – Paula Wood @ Time Out Bar & Bistro – 18:00-20:00
May 28th – The Kildeers @ Hotel Wolfe Island – 19:00-21:00
May 28th – Sea Songs and Sacred Anthems: Capella Regalis Choirs, Paul Halley @ St. George’s Cathedral – 19:00-20:30
May 28th – Spring Reverb: Slaves of Spanky, Pony Girl, Almond Milk @ The Broom Factory – 19:30-22:00
May 28th – REAL LOVE: Kenny & Dolly Tribute @ Kingston Grand Theatre – 19:30-21:30
May 28th – Spring Reverb: By Divine Right, Casper Skulls, Gifts of Guilt @ The Toucan – 21:00-01:00
May 28th-31st – Spring Reverb 2026 @ Various Venues – All Day
May 29th – Matt Dickson @ The Cove Inn – 17:00-20:00
May 29th – Christopher Jackson @ The Caesar Company – 20:00-23:00
May 29th – Spring Reverb: The Dirty Nil, Cam Kahin, Futura Free @ The Broom Factory – 19:30-22:00
May 29th – Bill Coleman @ Hotel Wolfe Island – 19:30-20:30
May 29th – Forever Seger @ Kingston Grand Theatre – 19:30-21:30
May 29th – Dave McGrath @ The Loaf N’ Ale Pub & Restaurant – 19:30-20:30
May 29th – Fresh Kils, Myer Clarity, DJ Versatile, ShizNick, Pretty Boi K.O., ClassAct & Ka… @ Overtime Sports Bar – 20:00-01:00
May 29th – Charity Drag Bingo: Rowena Whey @ Something In The Water – 20:00-23:00
May 29th – Vinyl Connection @ Time Out Bar & Bistro – 20:00-23:00
May 29th – The Sadies @ The Hayloft Dancehall – 20:30-23:00
May 29th – Mellow Lily @ Tir Nan Óg – 21:00-23:59
May 29th – Spring Reverb: Hot Garbage, Ace of Wands @ The Toucan – 22:00-02:00
May 29th – Luscious, Sticks n’ Stones @ The Merchant Tap House – 22:30-02:00
May 30th – Spring Reverb: Katarokwi Punk Rock Flea Market @ The Broom Factory – 11:00-15:00
May 30th – Spring Together @ Kingston Community Health Centres – 12:00-15:00
May 30th – Carnival of Song: Open Voices Community Choir @ Cooke’s-Portsmouth United Church – 14:00-15:30
May 30th – Carnival of Song: Open Voices Community Choir @ Cooke’s-Portsmouth United Church – 19:30-21:30
May 30th – The Hydeaways @ The Embassy Live Music Café – 19:00-21:30
May 30th – Spring Reverb: Thanya Iyer, Julia Finnegan, Pompey, Clara Smallman @ The Broom Factory – 19:30-22:00
May 30th – Spring Reverb: The Weber Brothers, Hannah and Nathan @ Hotel Wolfe Island – 20:30-23:00
May 30th – Forever Gala @ Isabel Bader Centre for the Performing Arts – 17:00- 23:00