The R.S. Gilmore Insurance Agency, Inc. was established in 1938 by Ralph S. Gilmore in a small office overlooking East Street in downtown North Attleboro. In 1961 after the untimely death of its founder Ralph S. Gilmore, Robert J. Gilmore and his brother Ralph A. Gilmore took over the ownership of the agency. They both ran an successful insurance agency but more importantly became pillars within the community for their involvement with numerous local charities and organizations.
In 1999, Timothy R. Gilmore became the third generation owner of the agency. He continued the growth of the agency and community involvement his father and uncle established. In 2008, Michael Michel joined the agency and in 2012 became part owner of the agency. Today over 75 years later, it has become one of the largest family owned insurance agencies in Southeastern Massachusetts.