Singing across the U.S., Kevin Montgomery plays Martha’s Vineyard

Kevin Montgomery performed at The Base Collective at the YMCA this past Friday, Sept. 14. — Photo by Gwyn McAllister

Last Friday night, Sept. 14, a small audience at the YMCA of Martha’s Vineyard’s Teen Center got to play a role in a unique nationwide initiative. Singer/songwriter Kevin Montgomery touched down briefly on the Vineyard for the midpoint concert of his ongoing 50 States in 50 Days tour.

Mr. Montgomery, a 2010 pick for CNN’s Most Intriguing People series, is completing the nationwide tour to raise money for the Orange Duffel Bag Foundation, an organization that provides coaching and advocacy for teens that have aged out of the foster care system. This is the performer’s fourth 50 in 50 tour. He also made a stop on the Vineyard during his 2010 country-spanning tour.

Thanks to his Island friends Ali Berlow and Kate Taylor, Mr. Montgomery was able to secure the Teen Center’s performance space – The Base Collective – at the last minute. He came with his keyboardist/vocalist Ruth Trimble straight from a show in New York City. He and Ms. Trimble performed an hour-long set of original country tinged tunes along with a couple of songs written by Mr. Montgomery’s father, Bob, who was Buddy Holly’s songwriting partner and best friend, as well as a successful music producer. Mr. Montgomery’s mother sang on a number of Elvis Presley recordings.

The Texas born musician has performed with Sheryl Crow and David Crosby, among others. He has recorded seven CDs on which he has enlisted country stars such as Lee Ann Womack and Trisha Yearwood for backup vocals. His sound, a mix of country, folk, and rock, has been compared to artists like Jackson Brown and Bruce Springsteen. His songs are heartfelt and infectious delivered in a high, clear vocal style.

Ms. Trimble, exhibiting a remarkably lovely voice, also performed a few original songs from her CD. In between songs Mr. Montgomery told inspiring stories about his trip, his father, and the cause he is so passionately involved with.

Mr. Montgomery not only books the dates (often while in transit) drives his own truck, sets up and performs – he also records post-performance video clips at every stop. During a break in the Vineyard concert, the enterprising musician showed a short video made up of interviews from his last tour in 2010. The video featured a number of kids who have received help from the Orange Duffel Bag Foundation as well as a few adult advocates answering the question, “Can one person make a difference in the life of a child?” It was a touching and eye-opening little glimpse into the work of the organization.

After the show, Mr. Montgomery videotaped audience members holding up a large handmade “Massachusetts” sign and singing the refrain from an original song, “Fear Nothing.” He is capturing similar scenes in all 50 states and will use the clips as part of a documentary he is making with BBC Radio 2’s Bob Harris.

In a post-concert interview, Mr. Montgomery talked about the work of the Orange Duffel Bag Foundation and the book co-authored by his sister, Echo Garrett, that inspired the initiative. He cited some unsettling statistics about foster children, such as 50 percent go homeless after the first six months of aging out and 70 percent of the U.S. prison population were in foster care at one time. Mr. Montgomery noted that he was inspired to undertake his first 50-state tour by a chance meeting with Peter Jenkins, author of the bestselling book, “A Walk Across America.” He said, “I thought, how can I do something similar to that?”

Despite numerous setbacks, Mr. Montgomery is forging ahead with the tour, which began in August in Alaska and will conclude in Hawaii. “Hopefully these tours will be an inspiring story of someone who won’t quit,” he said.

For more information about the Orange Duffel Bag Foundation, visit

Upcoming events at The Base Collective:

Community Open Stage 8–11 pm, Fridays, Sept. 21, 28. Perform music, dance, spoken word, poetry, comedy (clean please) & more. All ages. $5. Signup begins at 6 pm or call 508-696-7171 to claim a spot.