Fitchburg, MA Office
(978) 345-2505
Sterling, MA Office
(978) 422-7353

About Us


Our Values and Mission

Halstead-Flanagan Agencies values mirror our family values. Honesty, Loyalty, Mutual Respect, Hard work, and Support are some of the principles that we lay as the foundation when developing a relationship with each of our customers. We will work hard to educate & provide you with the best protection solutions with the best combinations of price & coverage for all your Personal & Business Insurance needs.

Our History

Robert L. Halstead Sr. founded Halstead Insurance Agency in 1966, which was and still is a family owned & operated independent insurance agency. As the family insurance business began to thrive, the agency's focus always remained the same. For almost 50 years we have strived to build a full-service agency that provides outstanding customer service while offering the best value in Personal and Commercial Insurance products available to our customers.

The current Halstead-Flanagan Agencies president, Anthony P. Trapasso Jr., Robert’s son-in-law, joined the agency in 1987. His concentration continues to be the development & expansion of our Personal Lines and Commercial Lines business which allows us to represent some of the leading competitive insurance companies in the country. In 2001, Ann Marie Halstead Trapasso, our CFO, began working at the agency. Michael Halstead, the agency's Operations Manager & Commercial Account manager, joined the team in 1991 and Kevin Halstead, also a Commercial Account Manager, joined in 1993. The business has grown steadily due mainly to a strong dedication to our loyal customer base. In 2018, Bob Halstead’s grandson, Anthony P. Trapasso III, joined the agency to help continue the Family Legacy of Service & Commitment to our clients and community.

On June 15th, 2011, M.J. Flanagan Insurance Agency, a family owned and operated independent insurance agency of Sterling, Massachusetts joined The Halstead Insurance Agency. Now formally known as the Halstead-Flanagan Agencies. The agency was founded by Michael J. Flanagan Sr. of Sterling, Ma. in 1928, a business he started right from his home. The agency had been a family owned agency since 1928 with Michael Sr’s sons., Paul J. Flanagan and Michael J. Flanagan successfully growing the agency to where it is today, with Paul retiring in 2011. Our experienced branch manager, Charlene Steele, continues to oversee the Sterling office.

Since 2011, the Halstead-Flanagan Agencies, has grown to a staff of 15 experienced & dedicated employees offering 2 locations. We are also a proud member of the Alliance Main Street Insurance Group which allows us to offer competitive options to our clients.

“Priding ourselves with long lasting customer relationships and believing that we go the extra mile for our clients” remains both our Fitchburg & Sterling agencies top priority!