Being a smaller city across the river from Detroit, a helluva lot of great entertainers and musical talent comes from and passes through Windsor, Ontario, on the regular.

As a result, there are some great venues that provide a much more intimate and lively concert and live show experiences in the city. Here are a few of our favourites that are really stepping up the live entertainment game in Windsor:

Phog Lounge

View this post on Instagram

A post shared by SCRAM (@scram519)


We can’t start a list about live entertainment in Windsor without Phog Lounge being at the very top. There’s a reason this tiny hole in the wall in the downtown core was named Canada’s best small live music venue by the CBC and has been the unofficial cultural centre of the city for the last 20 years.

This little red building that could has introduced the city to many up and coming acts throughout the years from Canadian East Coast legend Joel Plaskett to The Arkells to Classfied. Heck, even The Tea Party frontman, Jeff Martin, has been known to rip a few songs here and there on their Open Mic nights. 

Phog Lounge is known for practically never turning down any creative idea brought to them which has led to nights dedicated to poetry jam, jazz, and their very own creation, the Coaster Throwing Championships (seriously, you need to go and play) where patrons sign up to throw coasters at targets worth a varying amount of points with the most points on the night being declared the winner. You even get to choose your own walk-up song!

Something Special We Love: Try the poutine. Seriously. 

Villains Beastro

View this post on Instagram

A post shared by Villains Beastro Windsor (@villainsbeastro)


Right around the corner from Phog Lounge, Villains is part of a vibrant cultural district in the core that is steps from the Capitol Theatre, which the home of the Windsor Interntional Film Festival and the Windsor Symphony Orchestra. 

Villains takes a complimentary page out of Phog’s book by being amazing hosts to everything from disco drag shows to karaoke to live bands to disco nights. 

One of our favourite features of the establishment is how the walls are adorned with gorgeous portraits of some of the world’s most recognizable villains in history.

Something Special We Love: The villain portraits adorning the walls are also available to purchase in trading card format.

The Dominion House 

View this post on Instagram

A post shared by My Son The Hurricane (@mysonthehurricane)


Windsor’s oldest bar at over 140 years old, The Dominion House has quietly built a reputation for a great spot to take in live music. 

Affectionately known as The DH by locals, draws in a wide variety of individuals from the loyal regulars to students from the University of Windsor, located just a few blocks away. 

Something Special We Love: Almost all the locals and staff have a spooky ghost story about the place. Ask!

Walkerville Eatery

View this post on Instagram

A post shared by Walkerville Eatery (@walkerville.eatery)


Here’s a little twist on entertainment for the evening, but oh what a fun twist it is!

Every Saturday, from 8:00pm to 10:30pm, Walkerville Eatery owner, Mark Hawken, puts on a headset and does an interactive concert behind the bar as he’s serving drinks to customers.

It harkens back to the days of when Hiram Walker still roamed the streets of the company town he built that the Eatery is located in.

Something Special We Love: Their Caesars are something to behold!

Craft Heads Brewing Company

View this post on Instagram

A post shared by Curtis Coleman (@curtiscoleman_)


Every Tuesday night, Craft Heads Brewing Company hosts a free weekly comedy show that starts at 9pm called, Brewing for Comedy.

As a result, it’s provided a home to help nurture a lot of local comedic talent that can follow in the footsteps of local boy made big, David Merheje, who has won a June Award for Comedy Album of the Year, and stars alongside Daisy Ridley in, Sometimes I Think About Dying.

They have also begun booking “pro shows”, adding yet another element to the live entertainment in Windsor’s downtown core.

Something Special We Love: It’s a brewery whose motto is, “beer for the adventurous”. There’s always something new, exciting and unique to drink on their 50 taps!  

The Colosseum at Caesars Windsor

View this post on Instagram

A post shared by Anthony Lacaria (@anthonylacaria)


This is where the big boys come to play. With the strength and influence of a brand like Caesars behind it, the 5000 seat venue provides a more intimate setting for acts that have played stadiums.

From Tiesto to Celine Dion to Ice Cube to Bruno Marz, they’ve continually been hitting home runs with some of the most well known performers in the world. 

Something Special We Love: There’s also a smaller, free live music venue within Caesars called Cosmos Lounge.