Matthews entered politics in 1962 when he was elected to the Newburyport City Council.

During his tenure as mayor, Matthews oversaw much of the restoration of downtown Newburyport.

[3] In addition to serving as mayor, Matthews also worked for Massachusetts Governor Francis W. Sargent as an advisor[3] and campaign coordinator.

In 1983 he was a candidate in the special election to fill the Third Essex District seat in the Massachusetts Senate vacated by Sharon Pollard.

[5] In 1995, Matthews unsuccessfully challenged incumbent Lisa L. Mead in the Newburyport mayoral election.