For some it began with Go Dog Go, Busy, Busy Town or Green Eggs and Ham. The tears may have started with the dogs, Old Yeller, Sounder and Where the Red Fern Grows.

Sean Wilentz is hardly your Quaaludes and vitriol music critic. That may be why the Bob Dylan in America author was commissioned to write the definitive history of one of America’s truly great record companies. Mr. Wilentz is also the Pulitzer Prize-nominated author of The Rise of American Democracy: Jefferson to Lincoln.

Vacationing on Martha’s Vineyard is a Russo family tradition. “I’m trying to remember the first time we took my daughters to the Vineyard, but I know they’ve been coming every year since they were 10 or 11, maybe even earlier,” said novelist Richard Russo, who in 2002 won the Pulitzer Prize for fiction for his book Empire Falls.

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.

Best-selling author Adam Mansbach claims that he’s “really bad” at not working. He has spent a lifetime of summers at his family’s longtime home in Chilmark, times full of idyllic pleasures — bodysurfing, grilling fish from Larsen’s, living in a house overlooking a beach — that anyone would find enviable. But Mr. Mansbach cites his time on the Vineyard as his most productive as a writer.