Rogers & Gray Insurance
The story of Rogers & Gray Insurance Agency is steeped in history. It was the turn of the last century and Rogers & Gray was just starting to plant its feet on the sandy terrain that is Cape Cod, Massachusetts.
It was 1906 and Joseph L. Rogers was licensed to sell insurance. He began operating the Rogers Insurance Agency in the town of Orleans, MA; at the ‘elbow’ of the arm-shaped peninsula. His grandson, Francis Rogers, later took over the Agency and, in 1961, formed a partnership with Milton M. Gray, Jr., at which time the Agency became known as Rogers & Gray Insurance Agency, Inc.
Over the years the Agency prospered, and, in 1966, began to expand by opening a branch in the village of Hyannis, MA; the bustling ‘hub’ of Cape Cod, in the town of Barnstable.
Word of Rogers & Gray’s good work spread and less than a decade later, in 1974, another office opened up in Falmouth, MA; famed hometown to America the Beautiful author Katherine Lee Bates. The Agency continued to succeed and soon Sandwich, MA; the oldest town on Cape Cod, became the host of yet another Rogers & Gray branch. And it was then, in 1980, that Chuck Robinson, who had worked his way up to General Manager, acquired the ownership of Rogers & Gray and became its President and Chief Executive Officer.
In an effort to reach future friends over the Cape bridges, Rogers & Gray acquired the Plymouth Insurance Agency in 1985 in America’s historical “Hometown.” The Agency’s sixth office was opened in South Dennis, MA; in the center of the Cape, in 1987 and today that building now houses more than one third of its employees, and serves as the Agency headquarters.
The Hyannis branch grew in 1992 when the Spinnaker Agency was acquired and was merged into it. Another off-Cape agency, The Cape Insurance Agency of Plymouth, was also acquired, in 1993, and the Plymouth, MA office of Rogers & Gray was moved to that location. Agency expansion continued and the next year the Insurance Exchange was purchased and was merged into the existing South Dennis branch. In September of 1996, the Gilligan Insurance Agency in Sagamore Beach was acquired and, at the start to yet another century, in January 2002, Rogers & Gray acquired the Gifford & Eldridge Insurance Agency in Wareham, MA. In July 2009, furthering the goal of expansion off Cape, Rogers & Gray also acquired the E.A. O’Connor Agency in Norwell, MA.
Over the years, Rogers & Gray has become one of the top 10 independently-owned insurance agencies, in size, in Massachusetts and is approaching the status of being one of the top 100 independently-owned insurance agencies, in size, in the United States. This is due, in great part, to the commendable work ethic of the many employees Rogers & Gray has seen enter its doors over the years and the strong leadership skills of the Rogers & Gray management team.
Founded in 1906, Rogers & Gray is one of the top 10 independently-owned insurance agencies in Massachusetts and services over 23,000 customers. With 8 offices throughout Southeastern Massachusetts and a staff of more than 100 professionals, Rogers & Gray has direct relationships with dozens of insurance carriers to best represent the interests of their Personal, Business and Employee Benefits clientele.




