Traeger di Pietro moved to the Vineyard 24 years ago. Since then he has made a name for himself as a talented and accomplished artist. But one important accolade had eluded him: being the winning artist of the Martha’s Vineyard Agricultural Society fair poster contest.

But not for lack of trying.

“Nearly every year I have entered a painting,” he said.

Fair is August 15 to 18. — Traeger di Pietro.

His perseverance has paid off, though, as the Agricultural Society announced Friday Mr. Traeger’s painting of a family watching the rides together as this year’s winning entry.

Lauren Lynch, the Agricultural Society’s president, said in a press release that out of the 33 submissions, Mr. di Pietro’s submission stood out.

“It’s evocative of posters from the early and mid-1900s, yet reflects our Island today,” Ms. Lynch wrote.

The painting is also a personal one for Mr. di Pietro.

“Over the years, I have created a lot of animals, like a cow with a star on its face,” he said. “But then last year, when I was at the fair, I saw a couple standing by the fence watching the rides. And then I thought, what if that couple was me and my girlfriend and her kids.”

His girlfriend Lauren Evans is holding the hand of her 10-year-old daughter Marina, and her seven-year-old son Nico is dressed in a soccer uniform while standing beside his friend. Mr. di Pietro stands in the middle, wearing a blue and white checked shirt and straw hat.

But all the faces are looking away at the ride, so in a sense they can be anyone, which is what the artist wanted.

“That way it can be universal,” Mr. di Pietro said. “You don’t have to know it’s me and Lauren and Nico and Marina, but we know it is.

The family does not have a pet pig or chicken, which are both included in the painting, but animals in fair posters are almost essential.

“I knew I wanted the chicken holding the blue ribbon in its mouth,” Mr. di Pietro said.

For Mr. di Pietro, the agricultural fair is the quintessential family event of the summer.

“I like the idea of us standing there, taking it all in and enjoying the fair,” he said. “It’s timeless, and I always thought there would be nothing better than seeing kids walk around with a piece of my art on their backs.”

This summer, that is exactly what will happen.

The 162nd Martha’s Vineyard Agricultural Society Fair takes place August 15 to 18.