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Pembroke musician takes Highwaymen on the road

Singer-songwriter Matt York of Pembroke is performing concerts based on The Highwaymen in regional venues. He will be performing at the Pembroke Arts Festival on Sunday, Aug. 14.

Matt York is busy this month. He’ll be in Pembroke, Scituate, and other locales to perform his one-man show of songs by — and stories about — The Highwaymen, part of a yearlong concert tour in towns across Massachusetts.

The Highwaymen, a country music supergroup consisting of Johnny Cash, Willie Nelson, Kris Kristofferson, and Waylon Jennings, performed together from 1985 to 1995 and recorded three albums.

“I’ve done this performance at virtually every town in Southeast Massachusetts in recent months and am doing many more of them in the coming weeks,” said York, who lives in Pembroke. “What initially started as a way for me to fill in some dates and help pay the bills has mushroomed into doing over 120 performances across Massachusetts, mainly thanks to cultural council grants that I’ve received.”


The singer-songwriter grew up in Foxborough, graduated from Bridgewater State University, and has lived with his wife and two daughters in Pembroke for 15 years. A professional musician, he helped support his family through a “day job” with a telecommunications company. But when both his wife and he were laid off within a short period, paying the bills became a concern.

York said a fan of his Highwaymen show pointed him toward the state-funded cultural council grants awarded by every municipality. After some research he applied to them all and was awarded 100 grants.

“I found a niche,” York said of his performance schedule. A freelance writer in younger days, he also wrote a book, “The Highwaymen’s Songs and Stories,” and sells it at performances. Some of the venues have asked him to come back for a book-signing over the winter. Working in the evenings also gives him the flexibility to manage the family household, “get the kids off to school.”

Before finding his current grant-recipient niche, York had developed the show in which he performs the music and tells the stories of a legendary country music act formed by four previously independently performing and commercially successful artists.


More than a one-person “tribute” band, he performs songs made famous by The Highwaymen performing as a group, as well as the popular and often beloved songs associated with the performers’ individual careers. He also tells their stories.

“I basically try to tell stories about these guys’ careers and perform their songs solo,” York said. “I don’t dress in black,” he adds, alluding to Cash’s habitual concert attire. “The awesome thing is, the catalogue of the four of them had so many songs.”

He includes major hits such as Cash’s “Folsom Prison Blues,” Nelson’s version of “Always on My Mind,” and “Mammas Don’t Let Your Babies Grow up to Be Cowboys,” which was covered by Nelson and Jennings.

Concert venues include libraries, summer fairs, town concert series, and senior and community centers. “People who come out to these like music,” he said. “A lot of people are really impacted by those guys’ songs. So many people come up and just talk about a song that was part of their wedding.”

York said the appeal of country music artists is not limited to the southern and western parts of the country. His own tour took him to the “hill towns” in Western Massachusetts, which in earlier decades did not have good radio reception for popular music stations. However, a station with a strong signal emanating all the way from West Virginia carried into the hills, and many listeners got hooked on country’s star performers by listening to “Grand Ole Opry” shows.


“You don’t have to have owned a horse or a farm or a pickup truck to understand the feelings” behind these songs,” York said. “A lobster boat is the same as a farmer out West.” They have the same life struggles, he added. “Making a living … Drinking, love.”

Audience response to his Highwaymen shows has been great, he said. “And almost all of these concert performances are free.”

York will perform on Saturday, Aug. 6, at 2 p.m. at the Heritage Days festival in Scituate, a performance that includes some of his own songs backed by a full band.

He will also play on Sunday, Aug. 14, at 1 p.m., at the two-day Pembroke Arts Festival, taking place at the Hobomock Elementary School, 81 Learning Lane, Pembroke. For more information see

Robert Knox can be contacted at