Plymouth Rock Assurance auto insurance

Overview

Plymouth Rock Assurance is a regional auto and home insurer headquartered in Boston that sells only in the Northeast: Connecticut, Massachusetts, New Hampshire, New Jersey, New York and Pennsylvania. Its companies write and manage more than $2 billion a year in personal and commercial auto, motorcycle, homeowners and umbrella insurance across those six states.

The NAIC's Plymouth Rock Insurance Group ranked #37 among U.S. private passenger auto insurers by 2025 direct premiums written according to NAIC market share data, with $946.9 million in premiums and a 0.25% share. The Plymouth Rock brand is shared by two sets of companies. The underwriting companies behind the brand include Plymouth Rock Assurance Corporation, Pilgrim Insurance Company, the Bunker Hill companies, Mt. Washington Assurance Corporation, Plymouth Rock Assurance Corporation of New York and Plymouth Rock Assurance Preferred Corporation. In New Jersey and nearby states, many Plymouth Rock policies are instead written by Palisades Safety and Insurance Association, a New Jersey reciprocal insurer, and its subsidiaries, which Plymouth Rock Management Company of New Jersey manages as attorney-in-fact. That Palisades business appears separately in the NAIC ranking as Palisades.

Plymouth Rock sells through independent agents and directly by phone and online. Its Independent Agency Group alone manages more than $1.3 billion of personal auto, commercial auto, motorcycle and umbrella premium. In New Jersey, Pennsylvania, Connecticut and New York, Prudential financial professionals also distribute its products.

History

Jim Stone founded Plymouth Rock in 1982 and has been its CEO ever since. Before that he taught economics at Harvard, served as Massachusetts Commissioner of Insurance and, from 1979, chaired the U.S. Commodity Futures Trading Commission. The company says it is the only insurance company founded and headquartered in Boston in the last 40 years. It owns its headquarters building at 695 Atlantic Avenue, across from South Station, as well as 711 Atlantic Avenue and an office at 581 Main Street in Woodbridge, New Jersey.

Today the group also writes homeowners insurance through Plymouth Rock Home Assurance Corporation, the Bunker Hill companies and others. Plymouth Rock's direct-to-consumer and exclusive agent auto division is based in Woodbridge, New Jersey, and led by former GEICO executive Greg Kalinsky; New Jersey customers can also buy the Teachers' Insurance Plan, written by Teachers Auto Insurance Company of New Jersey. The Plymouth Rock Company's shares are not publicly traded; it commissions an independent appraisal of its Class A stock each year and publishes an annual report and chairman's letter.

Auto insurance coverage

Coverage follows each state's rules. In Massachusetts, a no-fault state, drivers must carry bodily injury liability, property damage liability, personal injury protection (up to $8,000 per person) and uninsured motorist coverage. Optional coverages include medical payments, collision and limited collision, comprehensive, substitute transportation (rental) and underinsured motorist coverage. Roadside assistance is optional on most Plymouth Rock policies and included on Teachers' Insurance Plan policies; it covers towing within 25 miles to the repair facility of your choice, with limits on the number of tows and fuel deliveries per year.

The GLASSCARE program repairs or replaces damaged glass for customers with comprehensive coverage, and the Get Home Safe benefit reimburses up to $50 once per policy year for a taxi or rideshare when it would be unsafe to drive.

Discounts and programs

Plymouth Rock runs three telematics programs depending on how you bought your policy:

• YUBI (Your Usage-Based Insurance), for direct customers in New Jersey, Pennsylvania, New York and Connecticut. Enrolling earns a participation discount of up to 10% at new business; at renewal, the best drivers can see rates up to 20% lower, and the worst up to 20% higher. Drivers who fail to complete the renewal requirements are removed and can see an increase of up to 20%.
• DriveSavely, for direct customers in Massachusetts, built into the Plymouth Rock app with similar pricing rules.
• Road Rewards, for customers of independent agents, which pays gift card rewards for safe drives.

Other discounts include a companion-policy discount for bundling auto with home, condo or renters coverage; a new driver family discount for policyholders of two or more years who add a driver with under three years' experience; an advance shopper discount for quoting more than seven days before the start date; and discounts for anti-theft devices, a safe driving record and members of sponsoring affinity groups. See telematics programs from the major insurers compared for how these compare with national programs.

Claims

Claims can be filed online, in the app or by phone. Customers who bought through an independent agent can call or text the claims team at 833-511-ROCK (833-511-7625); direct customers can call customer service at 800-437-5556 or the main line, 844-242-3555. Plymouth Rock's claim services are its signature:

• Crashbusters mobile claim service sends a representative to appraise damage at a time and place you choose, often with a check on the spot, at no extra cost.
• Photo appraisals let you submit pictures and receive an estimate within hours.
• Door to Door Valet Claim Service picks up your car and manages the repair, for customers with collision or comprehensive coverage.
• 100% Guaranteed Repair Shops guarantee work for as long as you own or lease the car, though you may choose any shop (see choosing a repair shop: direct repair programs and your rights).

Payments can be made by Zelle, direct deposit, paper check or eCheck.

Ratings and reputation

According to Plymouth Rock, AM Best has assigned an A- (Excellent) financial strength rating to each underwriting and managed insurance company in the group, as of October 2026 (see how AM Best ratings work). The company cites a February 2026 Wall Street Journal "Buy Side" article naming it the best car insurance company in Massachusetts, and workplace awards in Massachusetts and New Jersey. Complaints can be directed to each state's insurance department; because several underwriting companies share the brand, check which company issued your policy.

Who it suits

Plymouth Rock suits drivers in its six Northeast states who want strong hands-on claim service and the choice of buying direct or through an agent. Massachusetts and New Jersey drivers in particular will find it a long-established local alternative to national carriers. It is not an option for anyone outside the six states, and its telematics programs can raise as well as lower premiums.

• Strengths: Distinctive claim services (Crashbusters, Door to Door Valet, guaranteed repairs); choice of agent or direct purchase; A- (Excellent) AM Best rating on every company in the group; several discounts aimed at families and early shoppers.
• Weaknesses: Sold in only six states; YUBI and DriveSavely can increase rates by up to 20% for poor driving; brand spans many separate underwriting companies, which can make complaint and rating research harder; roadside assistance is optional on most policies.

How to contact Plymouth Rock Assurance