
VOTE YES on March 21
The good news:
The bad news:
Winchester is facing financial challenges.
Inflation and rising costs have regularly outpaced state limits on property tax revenue, which accounts for most of our town’s funding.
Without action, we face significant cuts to our schools, essential infrastructure repairs, and important community services, from DPW, to the Library, to even Public Safety departments.
Winchester is thriving in so many ways. As a town, Winchester is incredibly well managed from a financial standpoint – we are one of only two towns in the state with our profile to receive a AAA bond rating from Moody’s, reflecting the highest level of financial management. As a community, we’ve consistently shown up to support our town and our schools, making Winchester a wonderful place to live.
We have the power to make sure it stays that way. We all want Winchester to continue to be a place the next generation wants to return to raise their own kids. A place new families seek out for its great schools and close-knit community. A place with public buildings, schools, and spaces that we can be proud of and that serve our residents’ needs. We can do this by investing in a stronger and sustainable future, and coming together to provide residents of all ages with the resources and support they need.
How? By voting YES on a tax override on March 21, 2026.
This override is a vote between two futures: Do we want to continue to be a thriving community? Or risk becoming a town struggling to provide basic services?
Our Town Needs Our Support
Winchester has always been a community that shows up for our kids and seniors, that helps our neighbors, and supports our teachers, DPW workers, and first responders. A town that pulls together to make Winchester a place that we are all proud to call home.
Voting YES for the override will allow us to remain that kind of community.
This override is not about frills or “nice-to-have” extras. It is about creating the financial stability required to provide the basic services we need and expect from our town.
Voting YES will allow the town to fulfill critical infrastructure, safety, and school needs, while laying a stable and fiscally responsible foundation for the years ahead.
Voting YES will help us avoid a looming funding crisis so that Winchester continues to be a community we’re proud of – a community where residents of all ages can thrive.
Voting NO is not a vote to maintain the status quo. Voting no is a vote for cuts that will result in real harm to our schools and our town - cuts that will be felt by all of us.
Learn more about the override and why it's essential that we vote YES on March 21.

