Events Calendar
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Kids Eat Free
Friday, August 15, 2025, 3:00 PM to 5:00 PM
FRIDAYS 3pm to 5pm at Insomnia Restaurant & Lounge, Kids eat FREE*.
Don’t forget, WINE HOUR is also 3-5pm.Click here to view the Kids menu.
*Kids 13yrs and under eat free with an adult, from 3-5pm. -
Mixology Friday
Friday, August 15, 2025, 10:00 PM to 2:00 AM
Sophia is back behind the decks TONIGHT at Insomnia Restaurant & Lounge on Bloor, beginning at 10pm. The grooviest house. No cover. Discover what Mixology is all about. Drink specials.
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Wine Hour
Saturday, August 16, 2025, 3:00 PM to 5:00 PM
Wine Hour 3-5pm serves a featured wines and an amazing $7 per glass. Yes yes, Wine Hour is not just one hour, it is two!! AND... Wine Hour is every evening (not just tonight).
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Annex Session Saturday
Saturday, August 16, 2025, 10:00 PM to 2:00 AM
The Annex Sessions August presents the musical stylings of Legs Florentine.
Swing by for late night food and grooves every Saturday from 10pm - 2am. No cover. Drink specials after 10pm. Learn more about The Annex Sessions.
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Sunday Supper Club
Sunday, August 17, 2025, 5:00 PM to 10:00 PM
You are Cordially invited to Sunday Supper Club. This is an exclusive chef-curated, 5-course dining event, served only on Sundays from 5pm to 10pm. It's an intimate dining experience which serves two for only $59.95. Each month, the choices will be refreshed to delight your palate. See the full August menu.
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Tanzina Amin - Artist Series Opening Party
Sunday, August 17, 2025, 5:00 PM to 7:00 PM
Join Tanzina Amin as she launches her exhibit at Insomnia. Meet her and enjoy her pieces added to the walls at Insomnia. Be sure to reserve your table.
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Quickie Trivia Sunday
Sunday, August 17, 2025, 8:00 PM to 9:00 PM
Insomnia Restaurant & Lounge is doubling down on the brain power! We’re adding a second night of trivia.
Games will be an express style, perfect for a quick hit of fun before your work week starts. Plus! We will be crowd sourcing your thoughts on themes: Love Island? Friends? True Crime?!
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Andy Walker - Artist Series Showcase Opening Night
Sunday, August 17, 2025, 9:00 PM to 11:00 PM
Join us for an evening of thoughtful dialogue and artistic exploration as we celebrate Andrew Walker's distinctive approach to contemporary film photography. We invite collectors, art enthusiasts, and the broader cultural community to engage with this significant body of work.
For additional information and private viewing appointments, please contact us directly.
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Wine Hour
Wednesday, August 20, 2025, 3:00 PM to 5:00 PM
Wine Hour 3-5pm serves a featured wines and an amazing $7 per glass. Yes yes, Wine Hour is not just one hour, it is two!! AND... Wine Hour is every evening (not just tonight).
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Question Everything Trivia
Wednesday, August 20, 2025, 7:00 PM to 9:00 PM
Looking for the ultimate quiz night with a side of laughs and just the right dose of delightful chaos?! Every Wednesday, Insomnia delivers the dopest trivia showdown on Bloor, hosted by Question Everything's comedian Ari Issac and an ever-rotating cast of hilariously talented emcees.
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Miz Megs & Friends ~ Thursday
Thursday, August 21, 2025, 10:00 PM to 2:00 AM
Miz Megs & Friends every Thursday at Insomnia Restaurant and Lounge. Join resident DJ Miz Megs and her curated lineup of local legends each Thursday. Miz Megs' guests are DJs from the Toronto house and techno scene who you can find bumping beats around the city every weekend. No cover on Thursdays, Half price martinis, kitchen open til 2am. It's a party!! Learn more about Miz Megs & Friends.
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Kids Eat Free
Friday, August 22, 2025, 3:00 PM to 5:00 PM
FRIDAYS 3pm to 5pm at Insomnia Restaurant & Lounge, Kids eat FREE*.
Don’t forget, WINE HOUR is also 3-5pm.Click here to view the Kids menu.
*Kids 13yrs and under eat free with an adult, from 3-5pm. -
Mixology Friday
Friday, August 22, 2025, 10:00 PM to 2:00 AM
Cavo hits the decks TONIGHT at Insomnia Restaurant & Lounge on Bloor, beginning at 10pm. Cocktail specials. No cover. Discover what Mixology is all about.
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Annex Session Saturday
Saturday, August 23, 2025, 10:00 PM to 1:00 AM
The Annex Sessions August brings Oreku, himself.
Swing by for late night food and grooves every Saturday from 10pm - 2am. No cover. Drink specials after 10pm. Learn more about The Annex Sessions.
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Sunday Supper Club
Sunday, August 24, 2025, 5:00 PM to 10:00 PM
You are Cordially invited to Sunday Supper Club. This is an exclusive chef-curated, 5-course dining event, served only on Sundays from 5pm to 10pm. It's an intimate dining experience which serves two for only $59.95. Each month, the choices will be refreshed to delight your palate. See the full August menu.
-
Quickie Trivia Sunday
Sunday, August 24, 2025, 8:00 PM to 9:00 PM
Insomnia Restaurant & Lounge is doubling down on the brain power! We’re adding a second night of trivia.
Games will be an express style, perfect for a quick hit of fun before your work week starts. Plus! We will be crowd sourcing your thoughts on themes: Love Island? Friends? True Crime?!
-
Question Everything Trivia
Wednesday, August 27, 2025, 7:00 PM to 9:00 PM
Looking for the ultimate quiz night with a side of laughs and just the right dose of delightful chaos?! Every Wednesday, Insomnia delivers the dopest trivia showdown on Bloor, hosted by Question Everything's comedian Ari Issac and an ever-rotating cast of hilariously talented emcees.
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Miz Megs & Friends ~ Thursday
Thursday, August 28, 2025, 10:00 PM to 2:00 AM
Miz Megs & Friends every Thursday at Insomnia Restaurant and Lounge. Join resident DJ Miz Megs and her curated lineup of local legends each Thursday. Miz Megs' guests are DJs from the Toronto house and techno scene who you can find bumping beats around the city every weekend. No cover on Thursdays, Half price martinis, kitchen open til 2am. It's a party!! Learn more about Miz Megs & Friends.
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Kids Eat Free
Friday, August 29, 2025, 3:00 PM to 5:00 PM
FRIDAYS 3pm to 5pm at Insomnia Restaurant & Lounge, Kids eat FREE*.
Don’t forget, WINE HOUR is also 3-5pm.Click here to view the Kids menu.
*Kids 13yrs and under eat free with an adult, from 3-5pm. -
Wine Hour
Friday, August 29, 2025, 3:00 PM to 5:00 PM
Wine Hour 3-5pm serves a featured wines and an amazing $7 per glass. Yes yes, Wine Hour is not just one hour, it is two!! AND... Wine Hour is every evening (not just tonight).
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Mixology friday
Friday, August 29, 2025, 10:00 PM to 2:00 AM
Sophia joins forces with DJ Boots TONIGHT at Insomnia Restaurant & Lounge on Bloor, beginning at 10pm. Check out their collaborative brilliance. No cover. Discover what Mixology is all about. Drink specials and open kitchen til 2am.
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Annex Session Saturday
Saturday, August 30, 2025, 10:00 PM to 2:00 AM
The Annex Sessions August presents Katie B and DJ Jay Walk. Swing by for late night food and grooves every Saturday from 10pm - 2am. No cover. Drink specials after 10pm. Learn more about The Annex Sessions.
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Sunday Supper Club
Sunday, August 31, 2025, 5:00 PM to 10:00 PM
You are Cordially invited to Sunday Supper Club. This is an exclusive chef-curated, 5-course dining event, served only on Sundays from 5pm to 10pm. It's an intimate dining experience which serves two for only $59.95. Each month, the choices will be refreshed to delight your palate. See the full August menu.
-
Quickie Trivia Sunday
Sunday, August 31, 2025, 8:00 PM to 9:00 PM
Insomnia Restaurant & Lounge is doubling down on the brain power! We’re adding a second night of trivia.
Games will be an express style, perfect for a quick hit of fun before your work week starts. Plus! We will be crowd sourcing your thoughts on themes: Love Island? Friends? True Crime?!
-
Question Everything Trivia
Wednesday, September 3, 2025, 7:00 PM to 9:00 PM
Looking for the ultimate quiz night with a side of laughs and just the right dose of delightful chaos?! Every Wednesday, Insomnia delivers the dopest trivia showdown on Bloor, hosted by Question Everything's comedian Ari Issac and an ever-rotating cast of hilariously talented emcees.
-
Wine Hour
Thursday, September 4, 2025, 3:00 PM to 5:00 PM
Wine Hour 3-5pm serves a featured wines and an amazing $7 per glass. Yes yes, Wine Hour is not just one hour, it is two!! AND... Wine Hour is every evening (not just tonight).
-
Kids Eat Free
Friday, September 5, 2025, 3:00 PM to 5:00 PM
FRIDAYS 3pm to 5pm at Insomnia Restaurant & Lounge, Kids eat FREE*.
Don’t forget, WINE HOUR is also 3-5pm.Click here to view the Kids menu.
*Kids 13yrs and under eat free with an adult, from 3-5pm. -
Question Everything Trivia
Wednesday, September 10, 2025, 7:00 PM to 9:00 PM
Looking for the ultimate quiz night with a side of laughs and just the right dose of delightful chaos?! Every Wednesday, Insomnia delivers the dopest trivia showdown on Bloor, hosted by Question Everything's comedian Ari Issac and an ever-rotating cast of hilariously talented emcees.
-
Kids Eat Free
Friday, September 12, 2025, 3:00 PM to 5:00 PM
FRIDAYS 3pm to 5pm at Insomnia Restaurant & Lounge, Kids eat FREE*.
Don’t forget, WINE HOUR is also 3-5pm.Click here to view the Kids menu.
*Kids 13yrs and under eat free with an adult, from 3-5pm. -
Wine Hour
Saturday, September 13, 2025, 3:00 PM to 5:00 PM
Wine Hour 3-5pm serves a featured wines and an amazing $7 per glass. Yes yes, Wine Hour is not just one hour, it is two!! AND... Wine Hour is every evening (not just tonight).
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Wine Hour
Wednesday, September 17, 2025, 3:00 PM to 5:00 PM
Wine Hour 3-5pm serves a featured wines and an amazing $7 per glass. Yes yes, Wine Hour is not just one hour, it is two!! AND... Wine Hour is every evening (not just tonight).
-
Question Everything Trivia
Wednesday, September 17, 2025, 7:00 PM to 9:00 PM
Looking for the ultimate quiz night with a side of laughs and just the right dose of delightful chaos?! Every Wednesday, Insomnia delivers the dopest trivia showdown on Bloor, hosted by Question Everything's comedian Ari Issac and an ever-rotating cast of hilariously talented emcees.
-
Kids Eat Free
Friday, September 19, 2025, 3:00 PM to 5:00 PM
FRIDAYS 3pm to 5pm at Insomnia Restaurant & Lounge, Kids eat FREE*.
Don’t forget, WINE HOUR is also 3-5pm.Click here to view the Kids menu.
*Kids 13yrs and under eat free with an adult, from 3-5pm. -
Wine Hour
Sunday, September 21, 2025, 3:00 PM to 5:00 PM
Wine Hour 3-5pm serves a featured wines and an amazing $7 per glass. Yes yes, Wine Hour is not just one hour, it is two!! AND... Wine Hour is every evening (not just tonight).
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Andy Walker Artist Series Exhibition Closing Night
Sunday, September 21, 2025, 6:00 PM to 8:00 PM
Join us as we wish photographer Andy Walker a fond farewell and 'thank you' for sharing his work here at Insomnia Restaurant & Lounge. Meet Andy in this parting evening. View his work on our website. Reserve your table for this event.
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Question Everything Trivia
Wednesday, September 24, 2025, 7:00 PM to 9:00 PM
Looking for the ultimate quiz night with a side of laughs and just the right dose of delightful chaos?! Every Wednesday, Insomnia delivers the dopest trivia showdown on Bloor, hosted by Question Everything's comedian Ari Issac and an ever-rotating cast of hilariously talented emcees.
-
Wine Hour
Thursday, September 25, 2025, 3:00 PM to 5:00 PM
Wine Hour 3-5pm serves a featured wines and an amazing $7 per glass. Yes yes, Wine Hour is not just one hour, it is two!! AND... Wine Hour is every evening (not just tonight).
-
Kids Eat Free
Friday, September 26, 2025, 3:00 PM to 5:00 PM
FRIDAYS 3pm to 5pm at Insomnia Restaurant & Lounge, Kids eat FREE*.
Don’t forget, WINE HOUR is also 3-5pm.Click here to view the Kids menu.
*Kids 13yrs and under eat free with an adult, from 3-5pm. -
Tanzina Amin - Artist Series closing party
Sunday, September 28, 2025, 5:00 PM to 7:00 PM
We bid a fond farewell to Tanzina Amin as she closes her exhibit at Insomnia. Meet her and enjoy her pieces added to the walls at Insomnia. Be sure to reserve your table.