Singer songwriter Will Dailey delighted a crowd of Vineyard fans Saturday evening in an intimate concert at the Strand Theatre in Oak Bluffs. The free concert was sponsored by nonprofit Boston radio station WUMB-FM as a musical gift to its supporters.

Mr. Dailey has a large following in the Boston area, where he has won awards for album of the year, song of the year, and vocalist of the year at the Boston Music Awards ceremony. His music defies labels, and he said that’s fine with him.

Concert was a thank you from WUMB to its supporters. — Alison L. Mead

“I just like to use all the colors,” he said during a break in the sound check before the concert. “Sometimes that leaves you out of saying you’re folk or you’re rock or you’re indy or you’re Americana or you’re jam. I can’t imagine not being allowed to use any of these colors as a form of expression. I don’t want to go through life as an artist with only one set of tools.”

Among the most applauded songs in the set list Saturday was Three Hundred Dollar Man, a soulful anthem to farm families and others struggling to make a living. Mr. Dailey annually performs at Farm Aid, the concert and fundraiser founded by Willie Nelson.

He wrapped up the evening with his best-known composition, Higher Education, recorded with a banjo accompaniment on his 2014 album Sunken Ship but played during his Island concert on electric guitar.

I learned to dance from a girl who could dance,

far better than I could even breathe.

I learned to fight from an old man who could fight,

chase the dogs from the night with never having to swing.

All that I wanted was all in my mind.

And all that I need is to sing.

Mr. Dailey is currently on a tour that will take him to Milwaukee, Chicago, Indianapolis, Cleveland and Pittsburgh over the next month.