About Kailey
I have called Brookline home for over a decade. As a longtime community member, I have seen firsthand what makes this neighborhood special — and where it can do better. Town Meeting works best when representatives listen first and work together to solve issues.
I bring a wealth of experience as a large scale event/powwow planner, and theatre stage & production manager. These roles require skilled collaboration, communication, and inclusive problem solving between diverse stakeholders. As a Precinct 8 Town Meeting Member, I will fiercely advocate on behalf of our community, and center teamwork in policy making.
Links
Check out these links to learn more about my recent community collaborations and advocacy.
Brookline Indigenous Peoples Day Celebration, 2025
On October 13th 2025, the Brookline Indigenous Peoples Celebration Committee held an event featuring speakers, vendors, and free food. Featured Speakers Crystal and Aspen Johnson, Paul Mclean, and Kailey Bennett with a conversation on Gadugi.
Community Conversation on Killers of the Flower Moon
Bennett lives in Brookline now and is a member of Brookline’s Indigenous Peoples Celebration Committee, but she grew up an enrolled citizen of the Cherokee Nation in Oklahoma with an intimate knowledge of the story told in the film.
Indigenous Authors Book Club opens dialogue
Spaghetti westerns. Thanksgiving storybooks. School mascots. Hand turkeys. Much of American culture and knowledge associated with Indigenous people is rooted in stereotypes. The Indigenous Authors Book Club, however, digs deeper.
Brookline Indigenous Peoples Day Celebration, 2024
On October 14th, the Brookline Indigenous Peoples Celebration Committee held an event featuring speakers, vendors, and free food from the Native Kitchen. Featured Speakers Kailey Bennett, Asa Sevelius, and Kristen Wyman addressed “Indigenous Past, Indigenous Present, and Indigenous Future.”