It’s hard to pinpoint the best label to suit Louisa Gould. Is she a photographer, a painter, a business consultant or a sailor? She’s worked on Wall Street, photographed the Olympics and multiple sailing events and worked as a videographer. But this weekend, Ms. Gould will play the part of gallery owner, as she celebrates the 10th anniversary of the Louisa Gould Gallery, a fixture of the Vineyard Haven art community.

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.”

Warren Woessner, a self-described Renaissance man, is a poet, a chemist, a lawyer, and an active blogger. But on the Island, Mr. Woessner, 68, is primarily a “birdwatcher.” The term is, technically, outdated, he says, since bird enthusiasts began trying to distinguish themselves from the “little old ladies in their tennis shoes,” by referring to themselves as birders. Birding, which once meant hunting birds, now refers almost exclusively to the hobby of seeking the company of rare birds.

For many, the word opera evokes images of ornate costumes and talented vocalists singing to their tragic deaths. So it may surprise some to learn that Italian composer Giacomo Puccini ended his career with Gianni Schicchi, a farcical comedy. The libretto will make its way to the Island next week, when Wendy Taucher Dance Opera Theater stages a full production at Featherstone Center for the Arts in Oak Bluffs. The hour-long opera, Mr. Puccini’s only comedy, begins when a wealthy man, Buoso Donati, leaves his fortune to the church, instead of his family.

Ethel Skakel Kennedy declined interviews for more than 35 years. But when her eleventh child, Rory Kennedy, asked her to be the protagonist in a full-length documentary for HBO, she agreed.

“If you asked her, I think she would tell you it was because I asked her to do it,” Rory said. Ms. Kennedy is an experienced documentary film-maker but she was also hesitant about making the movie.

How do you like your Shakespeare? Light and comedic or deeply tragic? The Vineyard Playhouse is offering both this year in its annual summer run of outdoor Shakespeare productions at the Tisbury Amphitheatre. Those who fancy both will have the opportunity to see Twelfth Night and Romeo and Juliet, which are each running twice a week at the woodsy amphitheatre near the Tashmoo Overlook until August 18.

And this is Shakespeare with a slight gender twist.