Cold Days and Cool Bands: Live Music Winter 25/26
This region transforms into an intimate live music haven during winter months, with cozy venues hosting everything from folk and acoustic sets to Celtic nights and tribute bands. Local breweries, community halls, and historic theaters in towns like Huntsville, Bracebridge, Gravenhurst, and Parry Sound offer warm refuge from the cold, where you can catch talented local musicians and touring acts performing in charming small-town settings. The combination of snow-dusted landscapes, crackling fires, and soulful music creates a unique experience — one where the slower pace of winter allows for deeper appreciation of the artistry and community that thrives in Ontario’s cottage country year-round. Here are just some of the acts playing this winter:
Algonquin Theatre Huntsville
Hawksley Workman: Almost a Full Moon December 5
Tartan Terrors Celtic Christmas December 12
The Rock Singers of Muskoka Shuffle the Decades December 13
Jeff Martin December 15
Hotel California January 29
Abbamania Bee Gees February 6
The Red Hot Chili Pipers February 21
The Maple Blues Review February 22
Bala Bay Inn Bala
Charlie McKittrick December 31
Boston Pizza Gravenhurst
Check their Facebook Page for live music announcements happening regularly.
Boston Pizza Parry Sound
Check their Facebook Page for live music announcements happening regularly.
Bracebridge Hall
Cache Creek December 5
The Boathouse Blues Project December 6
Wheelhouse Band December 12
Brunswick Sports Grill & Pub Parry Sound
Check their Facebook Page for live music announcements happening every weekend.
Camp Bongopix Whitney
Live music Tuesday, Friday and Saturday in the Bongopix Tavern.
Canvas Brewing Co. Huntsville
Sean Cotton December 5
Live Music TBA December 6
Jack Gaughan December 12
Rich Howard December 13
Jack Gaughan December 19
Bluebird Days December 20
Erin Blackstock December 27
Charles W. Stockey Centre for the Performing Arts Parry Sound
Shawn Desman December 2
Dallas Smith + His Band: One Night Only December 8
A Merry Elvis Christmas December 11
The Good Lovelies: Holiday Concert December 12
Serena Ryder: Merry Myths Tour December 16
Handel’s Messiah December 20
Tommy Youngsteen – The Very Best of Creedence Clearwater Revival January 30
Union Duke February 28
Christie’s Mill Inn & Spa Port Severn
Check their Facebook Page for live music announcements happening regularly.
Clear Lake Brewing Co. Torrance
Check their Facebook Page for live music announcements happening regularly.
Deerhurst Resort Huntsville
Dallas Smith December 6
Jann Arden December 16
Blue Rodeo January 30 & 31
Di Salvo’s Hospitality Group Parry Sound
Check their Facebook Page for live music announcements happening regularly.
Fork on Main Kearney
Check their Facebook Page for live music announcements.
Gravenhurst Opera House Gravenhurst
Tim Baker with Rachel Bobbitt December 11
A Charlie Brown Christmas presented by the Sullivan-Parker-Kettlewell Trio December 12
The Griffin Pub Bracebridge
Live music almost every Wednesday, Thursday, Friday and Saturday. Click here for full calendar
Huntsville Festival of the Arts Huntsville
Hawksley Workman: Almost a Full Moon December 5 & 6
Dallas Smith December 6
Jann Arden Christmas Tour December 13
Jeff Martin of The Tea Party December 15
Blue Rodeo January 30 & 31
Shaun Booth – Live Your Legacy February 19
Red Hot Chili Pipers February 20
Maples Blues Review February 21
Jolly Roger Parry Sound
Live music every Saturday night. Check their Facebook Page for announcements.
JW Marriott The Rosseau Muskoka Resort & Spa Minett
Gowan December 31
The Mill on Main Huntsville
Check their website for live music announcements.
Music on Main Huntsville
Check their Facebook Page for live music announcements, open mic and karaoke nights.
The Oar Gravenhurst
Check their Facebook Page for live music announcements.
On The Docks Pub Huntsville
Live Music & Open Mic Night Every Wednesday
The Pub Burk’s Falls
Check their Facebook page for up to date listings
Rawley Resort Port Severn
Live Entertainment Friday & Saturday
Liz Anderson December 5
Shawn Mei December 6
Marlon Gibbons December 12
Mark Stewart December 13
Shawn Mei December 19
Mark Stewart December 20
Red Canoe Restaurant Kearney
Check their Facebook Page for live music announcements happening regularly.
Riverbowl Burk’s Falls
Live Music Every Saturday
Sawdust City Brewing Co Gravenhurst
Live Music Every Saturday
Smokin’ Hot BBQ Huntsville
Check their Facebook Page for live music announcements.
South River Brewing Co. South River
Check their website for live music announcements.
Theatre Muskoka Bracebridge
GODDO December 6
See the Joy December 19
Trestle Brewing Company Parry Sound
Check their Facebook Page for live music announcements happening regularly.