Three generations. One promise: insurance that's personal.
For nearly six decades, the Halstead family has helped Massachusetts families and businesses protect what matters most — the same way you'd want a trusted neighbor to.
ever since
Our values mirror our family values.
Honesty, loyalty, mutual respect, hard work, and support — these are the principles we lay as the foundation of every customer relationship. We work hard to educate you and provide the best protection solutions, with the best combination of price and coverage, for all your personal and business insurance needs.
- Independent — we represent you, not any single insurance company
- Family-run — three generations of the Halstead family, still hands-on
- Local — two Massachusetts offices and a team that knows the community
A legacy built one relationship at a time
Robert L. Halstead Sr. founded Halstead Insurance Agency in 1966 — a family-owned, independent agency that remains family-owned and independent to this day. As the business grew, its focus never changed: build a full-service agency that delivers outstanding service while offering the best value and coverage for every client.
Robert's son-in-law, Anthony P. Trapasso Jr., joined in 1987 and serves as President, focused on growing our personal and commercial lines and the leading carriers we represent. Ann Marie Halstead-Trapasso, our CFO, joined in 2001. Michael Halstead, our Production Manager, joined in 1991, and Kevin Halstead, our Senior Business Insurance Specialist, in 1993. In 2018, Robert's grandson, Anthony P. Trapasso III, joined the agency — carrying the family legacy of service into a third generation.
Our family grew, too. On June 15, 2011, M.J. Flanagan Insurance Agency of Sterling — founded by Michael J. Flanagan Sr. in 1928 — joined Halstead. On June 3, 2019, we merged with West Boylston Insurance Agency, originally founded in 1952. Together, these agencies bring nearly a century of combined local experience under one roof.
Today, Halstead Insurance Agency is a team of 18 experienced, dedicated professionals serving clients from two Massachusetts offices. As a proud member of the Alliance Main Street Insurance Group, we pair small-agency care with the buying power to offer truly competitive options. Priding ourselves on long-lasting customer relationships — and going the extra mile — remains our top priority.
Become part of the Halstead family.
Experience what personal, independent insurance service really feels like. Start with a free, no-obligation quote.