Milton residents faces a pivotal election season as candidates for five town boards grappled with a looming $300 million school construction estimate and the implementation of state housing mandates during the 2026 Milton Speaks Candidate Forum. Moderator Adam Cheers opened the event by emphasizing the high stakes of the upcoming votes, noting that candidates were not given the questions or subject before tonight's debate to ensure an authentic exchange of ideas regarding the town's fiscal future.

The Select Board race, featuring four candidates for two open seats, centered heavily on Milton's 97% residential tax base and the need for long-term financial planning. Megan Nolan, citing her experience managing hospital operating rooms, argued that this moment requires real discipline and transparency as the town faces a $16 million firehouse project alongside school costs. Pete Obersheimer suggested that the town must seek creative revenue streams, stating, We need to leave no stone unturned, from grant writing to increasing the commercial tax base or considering things like an Airbnb tax.

Addressing the pressure of state housing mandates, Roxanne Musto advocated for smaller-scale affordable developments that maintain a neighborhood feel, while Kevin Chrysom Jr. pushed for better integration between town bodies. We need the Select Board, Planning Board, and affordable housing trust in the same room, not operating in silos, Chrysom noted. Panelist Jose Zamora questioned how candidates would leverage their unique backgrounds, while Orla Cross asked for specific decisions to promote long-term affordability. John Orla Gordon pressed the candidates on balancing growth with Milton’s historical character, prompting Nolan to advocate for using data to weigh pros and cons rather than being reactive.

The Board of Assessors forum highlighted the technical challenges of valuing new multi-family developments. Tom Callahan, a 26-year Town Meeting member, warned that if we undervalue those, the burden shifts to single-family homeowners. His opponent, Warren Lizio, emphasized his 21 years in property management, noting that assessments should be evenly distributed based on the type of property. Mr. Neubauer questioned how the board would handle resident disputes, leading Lizio to highlight the office's open-door policy for walk-throughs. Callahan countered by suggesting that Milton needs to modernize, proposing evening office hours and a seat for assessors on the town finance working group.

The financial debate intensified during the School Committee session, where Dan O’Neal pointed to a 22% increase in school spending over the last five years. The school budget has to be transparent. I'm a 'show me' guy, O'Neal said, calling for a line-by-line expense audit. Sherice "Stevie" Caldwell focused on the upcoming search for a new superintendent, arguing the town needs a leader with financial acumen who can build strong relationships with educators. When Mr. Griffin asked about the timeline for a new school building, O’Neal noted the estimate has ballooned from $105 million toward $300 million, while Caldwell suggested that funding would likely align with a projected FY30 override.

Public health funding became a point of contention between Board of Health candidates Deborah Milbower and Roxanne Musto. Milbower criticized the town’s handling of nearly $500,000 in opioid settlement funds, noting that we've had opioid money for four years and only spent $45,000. She pledged to use her 30 years of public health experience to fund social-emotional learning projects in schools. Musto defended the current board's work, including the community health social worker program, and tied health outcomes to physical activity, stating, I'm the only candidate who has supported a turf at Lower Guile because I care about children's mental and physical health.

Finally, the Library Trustees candidates discussed the balance between modern services and infrastructure needs. Incumbent Christine Hodlin noted her work launching the writer-in-residence program, while John Folcarelli emphasized the need to be judicious with dollars given the competing needs of the fire station and schools. Mark Johnson suggested his background in technology would help the board ask the right questions about emerging tools like AI. Regarding a controversial parking expansion, Ellie Williams Fischer urged a cautious approach, suggesting the board should evaluate the proposal based on community input, cost-effectiveness, safety, and environmental responsibility.