Reply Each year the town holds annual elections on the first Tuesday in May. This year's election will be held May 4. (Patch Graphic) BROOKLINE, MA — Each year the town holds annual elections on the first Tuesday in May. This year's election will be held May 4. There are several contested races to watch, including a two-way race for Town Moderator. Five people are vying to fill two open seats on the Select Board, and there's also a two-way race for an open seat on the School Committee. All but three of Brookline's 16 precincts have races for Town Meeting members. There are also two ballot questions this year.