Our History

Located on Route 28, off exit 4 on I-495, the residents of Southeastern Massachusetts have enjoyed over 140 years of professional and trustworthy customer service. Established in 1877, our agency has always been a family owned business. T.M. Ryder Insurance was founded by Thomas M. Ryder and succeeded by his nephew, Charles Ryder at the turn of the century. Ralph W. Maddigan went to work for Charles in the early 1900’s and bought the agency from him in 1917. Ralph W. Maddigan Jr. joined the agency after serving in WWII. In 1972, Ralph W. Maddigan III joined the agency, and it was incorporated in 1973. Kira Watkins and Kristi Cornuet joined the agency in 2011 and 2015, respectively, and are the 4th generation in the family to be in the business. In 2017, T.M. Ryder celebrated 100 years of management in the Maddigan Family.

Our Team

Ralph W. Maddigan III



Ralph is the 5th owner of T.M. Ryder and the 3rd generation of ownership in the Maddigan family. He started with the agency back in 1972 and took over ownership in the mid-1980s. He built and moved T.M. Ryder to the current location on Thatchers Row back in 1985. He has been a licensed producer since joining the agency.

Kira Watkins

Office ManagerCommercial Lines CSR


Kira is the daughter of Ralph and the 4th generation in the family to work at the agency. She joined our team here at T.M. Ryder in January of 2011. She has a background in marketing and sales is currently in charge of those as well as networking for our agency. She is a licensed producer, specializing in commercial lines sales and customer service.

Kristi Cornuet

Marketing ManagerPersonal Lines Sales


Kristi joined our team in November of 2015. She is also the daughter of Ralph, and a 4th generation in the family in the agency. Her background is in marketing and sales, and she is a licensed producer, specializing in personal lines. She is jointly in charge of networking for the agency.

Kelly Restagno

Personal Lines CSR(Last Name A-L)


Kelly joined our team at T.M. Ryder back in 2000 and has been working in the industry since 1980. Kelly specializes in personal lines service bringing over 3 decades of experience to her work. She is dedicated to providing excellent service to customers.

Jenny Mason

Personal Lines CSR(Last Name M-Z)


Jenny started with us at the end of 2014. She has a background in customer service and in the auto industry. She brings to us a thorough knowledge of registry procedures, and is very familiar with the DRIVE Program and registration. She specializes in customer services in our personal lines department at the agency.

Agency Affiliations

o Cranberry County Chamber of Commerce

o Networking Group USA

o Power Hour Networking Group

o Massachusetts Association of Insurance Agents

o Professional Insurance Agents

o Independent Insurance Agents & Brokers of America, Inc.

Our Community

T.M. Ryder has been giving back and supporting the community that we insure for decades. Below is a list of several charities and causes we have donated to most recently. Please don’t hesitate to inquire with one of the members of our marketing team above. Thank you.

Giving & Community Involvement:

Middleboro Krazy Days (Middleborough on the Move)

Middleboro Youth Building Incorporated

Middleboro Police Superior Officers Local 96 N.E.P.B.A.

The Jimmy Fund/Pan-Mass Challenge – 2 Different riders

Oak Point Homeowners Scholarship Association

Old Colony YMCA – Middleboro

Wareham Gatemen Baseball, Inc.

Freetown Lakeville Youth Soccer

Middleboro High School Athletics

~ Steering & Securing Your Course for Insurance Since 1877 ~

-T.M. Ryder Insurance