Outerland, finished art by Mr. Kirkpatrick. — Ivy Ashe

Chris Kennedy, Martha’s Vineyard superintendent for The Trustees of Reservations, has spent the past 25 years touring Trustees properties on the Island. He’s seen Wasque, Mytoi, Norton Point and Long Point in all seasons and all types of weather, watching the landscapes shift and transform over time.

And yet Mr. Kennedy had never seen the properties as they were presented Sunday night, during an artists’ reception for the first Painting the Vineyard event, held at the Old Sculpin Gallery and sponsored by the Martha’s Vineyard Art Association. On Friday and Saturday, artists fanned out across the Island, taking advantage of what little respites from rain there were to set up their painters’ boxes and bring the Trustees’ properties to life on canvas. Twenty-five artists, most of them members of the Art Association, participated, producing the 52 works that hung on the Old Sculpin’s walls.

Proceeds from the sales benefit the Trustees, the Art Association and Old Sculpin. The partnership first came about after an Arts Association board meeting last September, when the group was brainstorming fund-raising ideas.

“Our idea was let’s paint out and showcase their properties,” said Janis Langley, co-chair of the event. “Of course, it rained; of course, it rained both days . . . .”

Abstract creations by Marston Clough. — Ivy Ashe

Still, the artists forged ahead, setting up portable studios at Mytoi, Dyke Bridge, Wasque, and Overlook Trail on Chappy, Norton Point in Katama and Long Point in West Tisbury. Knowing that not all artists are comfortable working outdoors — regardless of rainy condition — the Arts Association sent out a call for entry in the spring, so older work spotlighting Trustees properties could be featured in the show as well. The event also included nonmembers of the Art Association.

“This is an Island event,” co-chair June Shoppe said. “We have an amazingly generous artist community.”

Ms. Shoppe chose to paint at Norton Point, toting her French easel to the old South Beach entrance and working for three hours on an oil painting of the path. Hardy beachgoers stopped by to watch her progress throughout, she said, and her alla prima painting style impressed many onlookers.

“‘Two hours ago, it was brown blobs, and look at it now,’’ she recalled one person saying. Alla prima is a style of painting in which the artist creates a work in one take, layering wet paint over wet paint and working quickly to ensure that layers do not dry in between.

Brian Kirkpatrick braved the weather to paint at Mytoi. — Courtesy Brian Kirkpatrick

“I didn’t want to mess with it,” Ms. Shoppe said of the final product.

Some artists took a lengthier route to their final product. Artist Kathy Poehler spent three days on one of her works for the show, using strands of seaweed to recreate scenes from Mytoi, including a cedar tree and a footbridge. The challenge, she said, was balancing the strong lines of the bridge, formed by thicker pieces of seaweed, with the finer tendrils of red and green seaweed that swirled around it.

“It was an experiment, and I’m glad it worked out for me,” Ms. Poehler said.

Meg Mercier, a plein air painter, spent her Friday painting at the Dyke Bridge on Chappy. At Sunday’s reception she also purchased a painting by fellow participant Bob Fitzgerald.

“Sometimes you [just] see something by a friend . . . I think he was painting really well that day,” she said.

“Any artist is crazy about the Trustees properties,” Ms. Mercier said. “You can go out [to paint] and not see a house.”

Mr. Kennedy said that when people think of Trustees properties, they tend to think of oversand vehicles, piping plovers and erosion, but not necessarily the landscapes themselves. Having the artists interpret the scenery and refocus attention on the natural beauty of the Island “makes us very proud,” he said.

“To see [the landscapes] through someone else’s eyes — really, it’s amazing,” he said.