Plymouth Rock built its business on Northeast auto and home insurance sold through local independent agents, with service and claims staffed in the same states where it writes. Jim Stone, a former Massachusetts insurance commissioner, founded the group in 1982, and its companies now write and manage more than $1.3 billion in premium across Connecticut, Massachusetts, New Hampshire, New Jersey, New York, and Pennsylvania. Personal auto and homeowners form the core of the book, joined by condo, renters, and personal umbrella coverage. AM Best affirmed the Plymouth Rock Assurance Group Financial Strength Rating of A- (Excellent) in March 2026 and revised the outlook to positive.
