Six years ago Matt Casey brought one songwriter to perform and do a workshop on the Vineyard. This weekend he is bringing more than 15 musicians and songwriters to the Island as part of his New England to Nashville, Martha’s Vineyard Songwriting Festival.

The annual event has created a musical highway of sorts between New England and Nashville, the heart of country music. To some that may seems like strange bedfellows — Beantown rides in the back of a pickup truck. But Mr. Casey, founder of Neon Music Management, doesn’t think so. He grew up in Boston, lives and works in Nashville and his family has a home on the Vineyard. Why not bring together the places he loves?

It turns out Nashville musicians love the Vineyard too. “This time of year, Nashville still has oppressive heat and it’s landlocked,” Mr. Casey said.

But it isn’t just the beauty of the Island and a dip in the ocean that keeps them coming back, he added.

“What surprises them is how big music is on the Island. They know it’s a beautiful place but when they get here and see the music culture, everyone wants to come back.”

The event actually begins in Boston, with shows on Wednesday and Thursday night. It moves to the Vineyard on Friday, Sept. 15 with a barbecue at Mr. Casey’s house in West Tisbury. On Saturday, the songwriting workshops begin at Alex’s Place, the youth center at the YMCA, and continue on Sunday. There are also a number of live performances throughout the weekend by the musicians, who are separated into two categories, Rising Stars and established Hit Makers.

“But the more we do this, the more the lines are blurred,” Mr. Casey said, describing how many of the Rising Stars already have hit songs. In a sense, it becomes more about lived experience in the industry that separates the two.

The big show is Saturday night at the Strand Theatre, starting at 7:30 p.m. The musicians will also perform at various times on Saturday during Tivoli Day on Circuit avenue, and most likely some impromptu shows at local bars, including The Ritz on Sunday.

Lance Carpenter has made the trip each of the last five years, beginning as a relatively unknown Rising Star who later wrote Love Me Like You Mean it, which became a number one single on the country charts for Kelsea Ballerini.

Clay Mills is coming back for his third year. Mr. Mills is definitely an established Hit Maker, having penned number one hits for Darius Rucker, Diamond Rio and Kimberley Locke, as well as earning Grammy nominations for Trisha Yearwood’s Heaven Heartache and the Power of Love.

Mr. Mills said he started writing songs at a very young age. “I wrote my first song when I was eight or nine years old. It was called Don’t Throw My Love in the Trashcan.”

That song didn’t become a hit, but it started a journey. Mr. Mills grew up in Mississippi, splitting his time between living in a college town (his father was a professor) and a farm where his grandparents lived.

“It was good for me as a creative person,” he said about the split personality of the two places that raised him. After high school he attended the Berklee College of Music in Boston, getting his first taste of New England life.

“Boston to me is a very large small town,” he said, describing his affection for the city. “It has the bustle but also a small town feel.”

After school he moved to New York where he spent 10 years writing jingles for commercials. “Anything from the Armed Forces to Red Lobster,” he said.

At the age of 32 he moved to Nashville to pursue songwriting full time. Twenty years later he is still doing what he loves. “It’s the best job in the world if you can get it.” The best part, he said, is hearing from audience members about how a song moved them.

“Sometimes people will tell me how a song got them through the toughest part of their life,” he said. “I wasn’t there at the time, helping them out, but hearing that my song made a difference means a lot.”

Mr. Mills said there are a lot of foundational techniques necessary to writing a song, but it all starts with a true emotion.

“It can be happy or sad but it has to start in an honest, real place. This isn’t as easy to do as people think. A lot of people, when they sit down to write, want to hide themselves. But you can’t do that.”

Mr. Mills knows what he is talking about, and not just from his own experience of writing songs. With fellow songwriter, and workshop teacher Marty Dodson, he founded a school for songwriting called Songtown. The two men conduct in-person workshops, like the one this weekend on the Vineyard, but Songtown is mostly a virtual meeting place, where thousands of songwriters get together to share ideas and take classes.

“It’s a virtual town for people who want to write songs,” Mr. Mills said.

Mr. Casey echoed these thoughts when describing how much of songwriting gets done not in small, lonely rooms, but in community. In Nashville, musicians gather together in ‘rounds’ where they play together in a circle, swapping ideas and lyrics.

“It’s also the way musicians get to network,” Mr. Casey said. “It is the lifeblood of how you meet people.”

At the performance Saturday night, Mr. Casey is looking to recreate this experience for the audience by having the night begin with the musicians sitting in a circle, swapping stories and singing songs in a low key way. Later on, a full band will kick in as the Rising Stars perform their own songs and hit songs of their choosing.

The event is a fundraiser with every bit of the $75 VIP tickets going to Alex’s Place. VIP tickets include Friday night’s barbecue, a meet-and-greet before the Saturday show, and seats in the first four rows of the Strand Theatre. Islanders also get a $100 discount for the songwriting workshops. And everyone is invited.

“It doesn’t really matter what style you do or what age you are,” Mr. Mills said. “It’s about telling something that’s real.”

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