Plymouth Rock Assurance vs Safety Insurance

Verdict

Safety Insurance and Plymouth Rock Assurance are both Boston-based regional insurers with deep roots in Massachusetts. They overlap in Massachusetts and New Hampshire. Safety, publicly traded (NASDAQ: SAFT), wrote $701.5 million of private passenger auto premium in 2025 (0.19%). It sells only through independent agents in Massachusetts, New Hampshire and Maine, and says it is the fourth-largest auto insurer in Massachusetts. Plymouth Rock, privately held, wrote $946.9 million (0.25%) in its NAIC group. It sells in Connecticut, Massachusetts, New Hampshire, New Jersey, New York and Pennsylvania, through independent agents and direct by phone and online.

Safety's ownership is changing. In July 2026 it agreed to be acquired by an affiliate of MAPFRE, whose U.S. arm already writes a large Massachusetts auto book, and closing is expected in early 2027. AM Best affirmed Safety's A (Excellent) rating in July 2026 with a negative outlook, then placed it under review with developing implications because of the deal. Plymouth Rock says AM Best rates each of its companies A- (Excellent), as of October 2026. In New England in the J.D. Power 2026 U.S. Auto Insurance Study, Safety scored 616 (7th of 13) and Plymouth Rock 592. Both were below the 631 regional average.

Plymouth Rock stands out for hands-on claim service and telematics. Safety offers add-on packages and large clean-record discounts. Both can be quoted through independent agents, so get quotes from both.

Choose Plymouth Rock if

• You want to buy direct rather than through an agent, or want the choice.
• You value claim services such as Crashbusters on-site appraisals and Door to Door Valet repairs.
• You want a usage-based program (DriveSavely for Massachusetts direct customers, Road Rewards through agents), accepting that DriveSavely can raise rates.
• You may move to Connecticut, New Jersey, New York or Pennsylvania.
• You'd rather avoid an insurer in the middle of an ownership change.

Choose Safety if

• You live in Maine, where Plymouth Rock doesn't sell.
• You have a long clean record. Excellent Driver Plus is worth up to 24% in Massachusetts.
• You want Safety Shield or Safety Shield Plus, with a disappearing collision deductible and, in the Plus version, accident forgiveness.
• You want home and auto from one local insurer with a 10% account credit.
• You prefer to work through an independent agent and don't want telematics.

Key differences

Plymouth Rock policies are written by several underwriting companies, so check which one issued yours. If you buy from Safety, watch how pricing and service change after the MAPFRE deal closes. In Massachusetts, compare like-for-like on the car insurance quote comparison worksheet, and see regional car insurers: when smaller carriers can beat the giants for context.