Discover 57 professional Dixieland bands available in Windsor, Ontario, Canada for weddings, parties and special events. These traditional jazz ensembles bring authentic New Orleans style music with classic brass sections and vintage charm, backed by 139 reviews from real clients averaging 5 out of 5 stars.
All 57 suppliers listed here are willing to travel to Windsor. The nearest is based in Cleveland, United States, 88 miles away.
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Rates for Dixieland ensembles in Windsor typically run from about $230 to $2,400+, with an average booking fee of $950. Pricing reflects line-up size, performance duration and the group's experience. Many acts offer flexible configurations from intimate quartets to traditional seven-piece arrangements, allowing you to match both musical preferences and budget requirements. Contact the supplier you like for an accurate quote.
Based on 33 enquiries for Dixieland Bands at events in Canada, made through this site in the last two years. Updated 13 November 2026.
Jazz Connection
"10/10! Jazz Connection delivered an unforgettable performance. Their musicianship was top-notch, with every note full of energy and precision. They seamlessly blended classic jazz with modern vibes, keeping the audience captivated from start to finish. The chemistry between the band members was palpable, and their improvisations were nothing short of brilliant. Highly recommended for anyone looking to experience the best in live jazz!"
The Sidewalk Crusaders
"Great energy!!
We are so happy we booked The Sidewalk Cruisaders for our wedding. They brought so much energy and fun to our cocktail hour. My guests raved about them. Very easy to work with and willing to tailor the song list to our likes and interests."
Russell Wilson
"Russell was a wonderful addition to our party, not only his wonderful music, but also his fun personality."
Jazz Vocalist & Clarinetist Rick Bogart
"“ONE OF THE GREAT CLARINETISTS OF OUR ERA” - Danny Stiles WNYC Radio"
Musko Music
"Hi Brandon,
We just wanted to take a moment to sincerely thank you for being such an important part of our cocktail hour. I’m so sorry we didn’t get the chance to meet you in person, but please know that we were admiring your musical talent from all corners of the venue.
A special thank you for taking the time to learn songs that meant so much to us personally. Not every musician is willing to go the extra mile like that, and it truly didn’t go unnoticed. We received so many compliments throughout the evening about having you there, and we couldn’t have been happier with our choice. ☺️
You may not realize just how much it meant to us, but you added such a special touch to our celebration and helped make the evening that much more memorable. We’re genuinely so grateful. Thank you again 🙂
Best,
Maddy & Babs"
Texas Gypsies
"In a word... FABULOUS! These guys gave us just the sound we needed for our fun Prohibition-theme wedding. It is now two weeks later, and all we keep hearing is "Man, that band was fantastic!" They are worth the asking price (which is very reasonable to begin with!) Steve Curry is a great guy and very easy to deal with. I would recommend them without any reservations."
