On September 16,1903, a building permit was granted to C.H. Forrester to build a three story structure originally called the LeClaire Hall. Charlie Chaplin, while doing his vaudeville routine in Winnipeg, and staying at what is today the Windsor Hotel, (the LeClaire Hall at the time ) wrote his brother Sydney to tell him he had just signed his first movie contract. It was from here he left to go to the U.S to pursue film.

In 1930, the ownership,as well as the name changed to the Windsor Hotel. Just prior to the ownership change, $100,000.00 was spent on renovations to the bar and hotel. Quite a sum of money in those days.

In August of 1987, a proposal was brought forward to management at the Windsor Hotel, to re-introduce live music. The style of music proposed for the beverage room at the Windsor Hotel was the "Blues". The idea intrigued the owners, although they thought country would be better suited to the venue. After a number of head banging sessions, and a number of months later, the Windsor went "BLUES".

In the beginning, a relationship with a few of the blues musicians in Winnipeg, prompted the management of the hotel to call in a few favours to convince them to play at the Windsor. A few were not convinced, but there were those, Brian Ellis, Ben Sures, Harri Vallittu, and Mel Reimer, that did initially come in and try to help change the Windsor Hotel's reputation and appearance. Not long after, others, such as Brent Parkin, Dave Mowatt, Terry Barnett, Wally Landreth, Garry Preston, and many more came to play and frequent the Windsor. The nites dedicated to the blues were very limited in the beginning, starting with single Friday nites, then sporadic weekends (missing weekends if it was nice, cold and rainy, or if there was a feeling it would be a slow middle of the month). We progressed to booking every Friday and Saturday, Thursday, Friday and Saturday, and finally running music six days a week.

In 1993, the Windsor Hotel was at a stage where it had to expand to accommodate the larger crowds the blues was attracting. The addition to the beverage room was started in the fall of 1993, and completed in early 1994. Instead of seating 90 patrons, the Windsor hotel was now at allmost 200 seats allowing the hotel the opportunity to bring in not only local, but Canadian and International acts.

Over the years we have had many great names playing at the Windsor Hotel, way too many list here but, if you come down to the Windsor Hotel, and glance at our Wall of Fame, and talk to our friendly staff, they will fill you in.

We are now 100 years old, with 16 years of great blues history behind us. What has made this all possible, and as successful as it has been, has been the great bands and great customers, because without either we would just be four walls and a bottle of beer...... Thank you all for making and being a part of this history, past, present and future!