Discover 119 professional 1920s era musicians and bands available for hire in Boston, Massachusetts, United States, with an average rating of 5 out of 5 from 295 reviews from real clients. These vintage jazz ensembles focus on authentic 1920s entertainment and Great Gatsby-style performances.
All 119 suppliers listed here are willing to travel to Boston. The nearest is based in Fitchburg, 41 miles away.
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Rates for 1920s era musicians and bands in Boston range from $210 to $2,800+, with an average booking cost of $650. Pricing typically reflects the size of the ensemble, performance duration, and additional services such as period costumes or vintage equipment. Smaller jazz combos represent excellent value for intimate gatherings, while larger orchestras provide spectacular entertainment for major themed celebrations. Contact the supplier you like for an accurate quote.
Based on 171 enquiries for 1920s Era Musicians & Bands at events in the United States, made through this site in the last two years. Updated 15 November 2026.
A Touch Of Jazz Featuring Vin Cassotta
"I am delighted to recommend Vincent Cassotta of Enfield CT in pursuit of his grant application for the Louis Armstrong Tribute with a Jazz Quartet performing at the Eli Whitney Elementary School. My previous role as the PK-12 Music Coordinator for the Enfield Public School District has brought me in direct contact with the professional, innovative, creative, and artistic musician and retired teacher Mr. Vincent Cassotta. I have witnessed first-hand the impact and quality of his quality music instruction provided for his thirty-nine years of teaching tenure in our community. To have the opportunity to bring the genre of American Jazz Music as a tribute to the legend of Louis Armstrong with quality professional musicians under Mr. Cassotta’s organization is a blessing to the young minds and ears of our elementary students, especially at a time when music education in Enfield offers less opportunities.
This past Spring I had the opportunity to guest speak at Mr. Cassotta’s retirement party celebrating his many years of service in music education. In that speech I spoke about multiple areas beyond the collegial and professional relationship Mr. Cassotta, and I achieved since 1999. These in my opinion provide strong evidence for the Enfield Cultural Council to support this mission of this application fiscally. One of the points shared was that Mr. Cassotta balanced his career of music education and professional trumpet performing with incredible success throughout his career. Aside from the technical, logistical and time management responsibilities from such an endeavor, he achieved this success with never letting go of the care demonstrated to his students, family members, school building staff, and his music professional colleagues. The fact that he desires to continue to expand the music opportunities to students in Enfield now in his retirement resting years is evidence of his dedication to this art form and willingness to always educate.
Furthermore Mr. Cassotta’s wealth of experience professionally as a performing musician and student of the trumpet is stellar. In his education Mr. Cassotta studied trumpet with Rolf Smedvig of the Boston Symphony Orchestra and Empire Brass Quintet, Jimm Maxwell a NYC Studio Musician, Roger Murtha of the Hartford Symphony and Hartt School of Music, and Dan Patrylak of the Eastman Brass Quintet and UCONN. To continue, Mr. Cassotta was a freelance performer with Frank Sinatra, Manhattan Transfer, Ella Fitzgerald, Bobby Vinton, Bob Hope, The Four Tops, Phil Woods, The Temptations, Sammy Davis Jr., Andy Williams, Franki Valli and the Jimmy and Tommy Dorsey Orchestra. Including numerous local and state pit orchestra’s and local well know jazz bands. He has also published works as a composer and arranger with KJOS music as well as multiple professional recordings.
I strongly urge you to consider Mr. Cassotta’s application for this grant. Your support will help impact music education in Enfield and continue to make a meaningful impact on the lives of its students. Thank you for considering this recommendation.
Sincerely,
Mark F. Reppucci
Jazz, Orchestra, Music Technology and Piano Teacher
Enfield High School
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Leah Hinton Band
"Leah and her guitarist Noe sang/played at my wedding ceremony and reception and added SO much to the romantic yet playful ambience I had going on. Her voice is absolutely gorgeous and flexible, accommodating jazzy/soul numbers to indie and pop numbers alike. She was extremely communicative and helpful in choosing songs, playlists and had great suggestions that made my wedding absolutely perfect
Thank you so much Leah and Noe!!"
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!"
Andrew Thielen Big Band
"WE were so glad we found Andrew Thielen Big Band. They are a real band that has been together for over twenty years perfecting their music, showmanship and dazzling variety of music that kept our dance floor jammed. WE almost got swayed into one of these chain bands called Empire something where they throw together bands for one night until we figured out you cannot be a 3 piece band one week and a 12 piece band the next. WE wanted a real band where the band leader has had repeat performances for the most discriminating buyers for years. Every age, everyones taste in music and our twenty something wedding party had the time of our life. Call them now for sensational singers, instrumentalists and organization."
Crook & Company
"Robert and I are so over the moon grateful for the way Crook & Company graciously serenaded us and our guests for our wedding. You all did a phenomenal job with every detail. You were all professional, had amazing energy and extremely talented! You guys made the night perfect! I will definitely recommend your band in the future."
Hana Dolgin Saxophonist and Bandleader
"We have hired Hana a couple of times for our events on our yachts and she has even been available for us at very last minute with barely no time to prepare.
She is great as a person and everyone is always amazed with her music. We have hired her with a pianist as well as a guitar player on different occasions and each time she has given us a great show."
