Roslindale Jazz Festival Set for May 16
Special to the Gazette
The Roslindale Jazz Festival, scheduled for May 16, 2026, remains the premier cultural event of the spring season. Curated by local jazz pianist and composer Brian Friedland, the festival showcases the deep pool of musical talent residing within the neighborhood. The 2026 lineup includes an eclectic mix of ensembles, many of which are led by musicians with ties to the Berklee College of Music and the New England Conservatory.
Performances are distributed across two main stages: the Adams Park stage and the Birch Street Plaza. The festival is entirely free and open to the public, supported by the Mass Cultural Council and RVMS. Notable performers for the 2026 iteration include the Bill Pierce Quartet, AS3, and TickleJuice, providing an afternoon of world-class music in the heart of the village. This event not only highlights local artistry but also drives significant foot traffic to the surrounding brick-and-mortar businesses in the square.
If you can’t make it to the Jazz Festival, worry not. Roslindale’s jazz scene thrives year-round through the Jazz Sundays at the Square Root series. Produced by Brian Friedland since 2019, this twice-monthly residency transforms the local eatery into a dedicated listening room where the music takes center stage.
The 2025-26 season continues through June, typically held on two Sunday evenings each month. The series offers a unique mix of curated performances by Boston’s top-tier jazz artists and themed jam sessions that welcome emerging talent. While the setting is intimate, the atmosphere is 100% focused on the artistry, providing a rare “club” experience in the heart of the neighborhood.
Event Details:
Time: Doors generally run from 7:00 PM to 9:30 PM.
Admission: A $10–$20 cover charge at the door directly supports the performing musicians (with a $5 discount for participating musicians on jam nights).
Support Local: Attendees are encouraged to enjoy food and drinks from The Square Root to help sustain this long-running series.
For the full lineup of the remaining season, visit
brianfriedland.com/jazz-
sundays–the-square-root.html