Music
Events
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Toronto All-Star Big Band at Muskoka Chautauqua
Muskoka Chautauqua: Theatre in the Woods 1039 Golf Avenue, Windermere, ON, CanadaEnjoy the big band sound under the stars with the Toronto All-Star Big Band during the Muskoka Chautauqua Summer Festival. This exciting young band brings the spirit, style and sound of the 1930s, 40s and 50s to life, celebrating the golden age of big band music with vibrant energy, choreography and nostalgia. Don’t miss this [...]
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Forever Plaid at Gravenhurst Opera House
Gravenhurst Opera House 295 Muskoka Rd S, Gravenhurst, OntarioEnjoy the nostalgic charm of Forever Plaid at Gravenhurst Opera House from August 11 to 19. This hilarious and heartwarming musical revue is filled with classic barbershop quartet harmonies, pitch-perfect melodies and beloved hits from the 1950s. The story follows four earnest young men who dream of becoming a popular quartet and are given one [...]
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Basset at Duke’s Live Music
Duke Boats Limited 2 James Bartleman Way, Port Carling, ON, CanadaEnjoy an intimate night of live music with Basset at Duke’s Live Music in Port Carling. Known for their warm harmonies, thoughtful songwriting and folk-inspired sound, Basset brings a beautiful listening-room experience to Duke’s historic second-storey wooden boat shop. With limited seating, great acoustics and a relaxed Muskoka atmosphere, this is a special summer concert [...]
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Briar Summers at Windermere Pub
Windermere Pub 2508 Windermere Road, Windermere, ON, CanadaEnjoy live music with Briar Summers at Windermere Pub on Friday, August 14. Raised in the Huntsville and Lake of Bays area, Briar is a singer-songwriter with deep Muskoka roots and an alt pop-rock sound. She has been performing since childhood and brings a warm, expressive style to the stage. Settle in for a summer [...]
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Folk Night with Beverlie & Friends
Muskoka Chautauqua: Theatre in the Woods 1039 Golf Avenue, Windermere, ON, CanadaEnjoy an evening of folk music, harmony and unforgettable live performances during the Muskoka Chautauqua Summer Festival. Hosted by Canadian folk pioneer Beverlie Robertson, this special concert brings together an extraordinary collection of women on the outdoor stage in Windermere. The evening features Beverlie Robertson, Christina Hutt and Trish Foster, and Leah Leslie and Tamica [...]
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The Sheepdogs Concert at The Kee to Bala
The Kee to BalaThe Sheepdogs also play on Saturday, August 15th! Get tickets for the Saturday show here: The Sheepdogs Tickets Aug 15, 2026 Bala, ON | Ticketmaster
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Jaclyn Kenyon at Windermere Pub
Windermere Pub 2508 Windermere Road, Windermere, ON, CanadaEnjoy live music with Jaclyn Kenyon at Windermere Pub on Saturday, August 15. A Canadian singer-songwriter with powerful vocals and a bold, rock-influenced sound, Jaclyn brings emotional honesty, energy and strong stage presence to every performance. Settle in for a memorable summer night of live music, great food and good company in Windermere.
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Gina Horswood at Duke’s Live Music
Duke Boats Limited 2 James Bartleman Way, Port Carling, ON, CanadaAustralian singer-songwriter Gina Horswood, now based in Muskoka, returns to Duke’s Live Music on Saturday, August 15. With a career shaped by touring across Australia, Nashville and North America, Gina brings heartfelt songwriting, rich storytelling and an intimate acoustic sound to the stage. Her music reflects a life of travel, creativity, resilience and connection. Gina [...]
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Heart Lake Road at Sip n’ Sounds
Muskoka Lakes Farm and Winery 1074 Cranberry Rd, Bala, Ontario, CanadaEnjoy an afternoon of live music with Heart Lake Road at Sip n’ Sounds on August 16 at 2pm. Rooted in the Almaguin Highlands, this family trio is led by Burk’s Falls country favourite Pam Millar, whose soulful blend of country, rock and blues has earned her a loyal following across Muskoka and beyond. With [...]
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Mitch Beube & Jason Crawford Duo at Windermere Pub
Windermere Pub 2508 Windermere Road, Windermere, ON, CanadaEnjoy live music with the Mitch Beube and Jason Crawford Duo at Windermere Pub on Sunday, August 16. Featuring saxophone and guitar, this talented duo brings a smooth, relaxed sound to the stage for a summer evening in Windermere. Settle in for great food, good company and live music from 7pm to 9pm.