Director Kevin Ryan stands inside the Performing Arts Center at the regional high school rehearsing for the Island Theatre Workshop’s latest production.

“Munchkins!” he calls to the group of children sitting the front row of the theatre. The kids talk and giggle and tick-tock their feet.

“Does everyone have a hat tonight?” Mr. Ryan asks. “We’re going to start in a minute.”

For two weekends in August Oak Bluffs goes dancing. The beating of drums begins around 7:30 p.m., beckoning people to the corner of Grove and Narragansett avenues. Inside Union Chapel dancers sway and stretch and leap, warming up to the drumbeats.

On Friday evenings during August, Vineyard Gardens in West Tisbury is transformed into a community art gallery. Works of art are arranged among the plants and paintings are hung from benches turned on end.

“The idea came from wanting to support the local artists and knowing that our flowers would complement their work and their artwork would complement our flower plant displays,” said Christine Wiley, who owns Vineyard Gardens with her husband, Chuck Wiley.

At Owen Park, in downtown Vineyard Haven, a little red trailer is hitched to the back of a Chilmark Spring Water van. On the side of the trailer, painted in expansive gold script, it says: The Vineyard Haven Band Est. 1868.

Frank Dunkl, owner of Chilmark Springwater with his brother and sister, serves as the band’s board president, french horn player and passionate historian.

In 1985 painter Andrew Moore spent his first full year on Martha’s Vineyard. He lived in a one-room cottage that housed the essentials: a bed, a wood stove, an easel, his dog and a surfboard. Mr. Moore had recently graduated with his bachelor’s degree in architecture and this was his leap into a life of full-time painting.

Maggie Shipstead was not yet 30 when she finished her first novel, Seating Arrangements. The story, as she described it in a recent interview, is about “an ever-so-slightly dysfunctional Waspy family holding a shotgun wedding on a resort island.”

Ms. Shipstead has never been to the Vineyard before. It is of Nantucket that she speaks, naturally.