After clown school shut down unexpectedly, May Oskan was a little lost and rather bitter.

“The floor went out from under me... I didn’t have my community, teachers or classmates,” said Ms. Oskan of her time at the San Francisco Circus Center. “I didn’t have my tightrope or anything to juggle. I was a clown with no circus.”

Always one to be involved in a project, Ms. Oskan knew she had to do something big.

“And I knew I didn’t want it to be funny,” she added with a laugh.

The Pit Stop is located inside an inconspicuous garage across the street from Tony’s Market in Oak Bluffs and is hard to find even when you’re looking right at it. A small marquee out front advertises the night’s musical entertainment and a white hand-painted sign directs visitors around an old trailer to the entrance at the back of the building.

A few weeks ago, while sitting on a porch here on the Vineyard, Jessica Ashley leaned back, closed her eyes and began to sing. Or rather, she belted out a few lines, totally absorbed in the music. Afterwards she opened her eyes and asked, “Do you know that one? My sister and I used to sing that one together.”

This Monday, August 6, will bring an unlikely visitor to the Island, a Dodd harpsichord. It’s not a total stranger to the Island, but Chamber Music Society artistic director Dee Stevens estimates that it’s been 20 years since it’s been heard here. This Monday and Tuesday, Ms. Stevens will play the rare instrument in a chamber music concert featuring the music of Johann Sebastian Bach and his sons.

Arnold McCuller has sang with Aretha Franklin, Diana Ross, Bette Midler, Beck, Bonnie Raitt, Lyle Lovett — the list goes on and on. But mostly the list begins and ends with James Taylor.

The Vineyard is not the tiny, sunny Island that birthed the smooth and rhythmic sounds of reggae music, but it will be the one to host some of the genre’s legends on August 14.

The Wailers, most famous for their work with Bob Marley, are performing at The Lampost in Oak Bluffs at 8:30 p.m. Tickets are $32 in advance and $40 the day of the show.

Special guests include Junior Toots, Mike Martin y Los Rootsticks and Selectah Niko of One Drop Sound System. The show is presented by Nectar’s Presents and Rolling Rock.

Folksinger Greg Brown got his first professional gig in the 1960s at the age of 18 and later became a record producer. He will be performing at Union Chapel.

Danny “Kootch” Kortchmar got his start playing in bands such as the Kingbees and the Flying Machine. There was another skinny, long-haired fellow in Flying Machine named James Taylor who, at the time, was like Danny — just another Vineyard summer dink with a guitar and a melodic voice. Kootch and JT, the early incarnation of the Chilmark Potluck Jam.

When Peter Asher first heard Kate Taylor sing, he was instantly impressed. “I loved the texture of her voice and her phrasing, so I said, let’s make a record.”

Not one for idle chatter, Mr. Asher then produced her first record, Sister Kate. The year was 1971.

“She was even more of a soul singer devotee than James [Taylor] was,” Mr. Asher remembered. “He took after Sam Cooke and Ray Charles, but Kate was rocking out and blues-ing out much more overtly. I loved that she was a white soul singer.”

On Monday John Lee stood in the Tabernacle, excitedly talking about the second annual Martha’s Vineyard Jazz Festival. It was the same place he first came up with the idea. He pointed to the front few rows. “I sat in these pews with my daughter and visualized having a festival,” he said.

At the time there was nothing on stage. He was simply sitting and dreaming.