Discover 238 oldies bands and golden oldies groups available in Windsor, Ontario, Canada, bringing vintage music entertainment to weddings, parties and special events. These nostalgic performers, rated 5 out of 5 by 416 reviews from real clients, specialize in classic hits from the 50s through 70s.
Of the 238 suppliers listed here, 5 are based within 30 miles of Windsor. The other 233 are willing to travel there.
Also covers suppliers based in Detroit, Clinton Township and Fraser.
(3) Replies in < 1 hr
Book from $1500 (USD)
Add to favouritesNo reviews yet
Book from $400 (USD)
Add to favouritesNo reviews yet
Book from $300 (USD)
Add to favouritesNo reviews yet
Book from $300 (USD)
Add to favouritesBased more than 30 miles from Windsor, nearest first
No reviews yet
Book from POA
Add to favourites(3) Replies in < 1 hr
Book from POA
Add to favouritesNo reviews yet
Book from $2000 (USD)
Add to favouritesTell us about your event and we'll suggest suppliers, or talk to our team.
Choose a town or city to see suppliers who work there.
Acoustic Bands in Windsor
Acoustic Duos in Windsor
Alternative Bands in Windsor
Blues Bands in Windsor
Classic Rock Bands in Windsor
Cover Bands in Windsor
Easy Listening Bands in Windsor
Heavy Metal Bands in Windsor
Indie Bands in Windsor
One Man Bands in Windsor
Party Bands in Windsor
Pop Bands in Windsor
Punk Bands in Windsor
Rock 'n' Roll Bands in Windsor
Rock Bands in Windsor
Soul Bands in WindsorRates for oldies bands in Windsor currently range from about $280 to $4,300+ depending on group size, performance duration and specific requirements. The average price of $950 typically includes professional sound systems, microphones and often period-appropriate staging elements. Factors affecting pricing include travel distance, event duration, special song requests and whether additional services like DJ sets between live performances are included. Contact the supplier you like for an accurate quote.
Based on 77 enquiries for Oldies Bands at events in Canada, made through this site in the last two years. Updated 13 November 2026.
ALX - The Ashley Lynn Experience
"What an awesome show.
I’ll be back tonight (and again and again...)."
Denise Davis and the Motor City Sensations
"Annette Wernert recommends Denise Davis and the Motor City Sensations.
We had a great time at your concert at Eastpointe City Hall! You are all very talented and gifted performers. Thank you for a wonderful evening!"
All Of Me
"The All of Me show was outstanding, one of the best performances I've seen, Paul Gordon and the band outstanding, his tap dancing super, You don't want to miss it."
Paul Cohen Piano
"Paul was great! He was accommodating when we asked him to play a custom song for our wedding ceremony and his personal jazz music was perfect for our cocktail hour. He was quick to respond to our emails and was the most professional vendor we worked with, we highly recommend him!."
The Kensie Jazz and Dance Band
"Perfect Jazz Band!
Secured The Kensie Jazz Band for our 30th Anniversary corporate event. From start to finish they were perfect. Perfect background music while guests are engaging in the social circuit. Perfect background music while being seated and served for dinner. The band can adjust their sound level to your preference. They play a range of music. A live band is a classy touch and adds ambience to any event rather than a standard DJ. It is a completely different vibe. Nice group of people! Good pricing as well. Thank you!"
Swing Shift Big Band/Wedding Band
"Thank YOU and the band so much - I'm only sorry we cut into your playing time (speeches and photos)! Everyone absolutely loved the band and was blown away by your sets- we'll hope to catch you and the full Swing Shift band at the Rex sometime in the future and buy you a drink!"