Faint smudges of paint marked the bottom of Brooke Adams’ slip-on shoes, remnants of a late night spent painting the guest room just off the porch of her Chilmark home. Ms. Adams and husband Tony Shalhoub were up until nearly 1 a.m. the night before, putting on the finishing touches. House guests would be arriving soon, and the ro om didn’t have its summer coat yet.

Some eight hours later, the paint still wasn’t quite dry, but the floor was a lovely lavender, and the walls a pastel summer green. The entire job took two days.

“We had to put a different kind of paneling on the wall in order for it to work,” Mr. Shalhoub said.

Whether embarking on home renovations or rehearsing for an upcoming performance, working together seems to be what Ms. Adams and Mr. Shalhoub enjoy most. On Monday, the actors will partner onstage at the Performing Arts Center at the regional high school in Carol Rocamora’s I Take Your Hand In Mine as a benefit for the Vineyard Playhouse. The play is based on the love letters of Anton Chekhov and Olga Knipper.

The stage is a comfortable home-away-from-home for both actors. Ms. Adams grew up in an acting family, starred in Days of Heaven, and has continued to work in both film and television. But, she said, “I grew up in summer theatre, so I have a particular love for that.”

One-night-only performance is a benefit for the Vineyard Playhouse. — Anthony Esposito

Perhaps best known for his film appearances and his Emmy-winning television work on Monk, Mr. Shalhoub made his Broadway debut in 1985. He also just finished a Tony-nominated turn in James Lapine’s Broadway adaptation of Act One, in which he played three different characters and immersed himself so thoroughly in the roles, his own brother didn’t recognize him in the first scene.

“No idea,” Mr. Shalhoub said. “My brother, who I’ve known my entire life.” The play had more than one Vineyard connection. Writer-director Mr. Lapine is an Edgartown resident and workshopped the piece at the Vineyard Arts Project.

Ms. Adams and Mr. Shalhoub’s connection to the Vineyard Playhouse is well-established. They have done readings there for years, often with fellow theatre friends from New York and Los Angeles, and have been involved with the fundraising campaign for the newly renovated space since its inception. And last summer, when the new lobby first opened, Ms. Adams exhibited paintings there. Oldest daughter Josie has worked with the playhouse’s Summer Stars program.

“It’s just an opportunity to give back to this community,” Ms. Adams said. She laughed. “And show off, which is my favorite thing.”

A Chekhovian love story told onstage is particularly fitting for the pair, who first met in 1989 when both were cast in The Heidi Chronicles during its Broadway run. Ms. Adams had already felt a strong connection to the Pulitzer-winning piece when she was offered the role of Heidi, a New Yorker navigating the feminist revolution of the 60s and 70s. At the end of the play, Heidi decides to have a baby on her own — a striking coincidence for Ms. Adams, who had just adopted daughter Josie.

“I felt totally connected to the piece because of the adoption thing, and [then] Tony and I met,” Ms. Adams said.

“And here we are,” Mr. Shalhoub said. Mr. Shalhoub played Scoop, Heidi’s main romantic interest. The play continues to be influential for the family: one of the couple’s three dogs is a Goldendoodle named Scoop.

Ms. Adams and Mr. Shalhoub have continued to collaborate across mediums. They’ve done innumerable readings together, and performed so many Chekhov pieces that the works are hard to keep straight. Ms. Adams appeared in five episodes of Monk, and in 2002 Ms. Adams starred in Made-Up, a film written by her sister, Lynne Adams, and directed by Mr. Shalhoub. The couple acted together in a David Mamet play in Boston, and returned to Broadway four years ago to star in Lend Me A Tenor, which was staged in the building across the street from where The Heidi Chronicles first opened.

“It’s just an opportunity to do what we love to do, but not be separated while we’re doing it,” Ms. Adams said. “We both have a lot of respect for each other as actors.”

After the playhouse performance, they will begin rehearsing for a six-week run of Samuel Beckett’s Happy Days, which will open in Pasadena, Calif., in September. There are just two roles in the play, so director Andrei Belgrader, who worked with Mr. Shalhoub on Monk, plans to travel to the Vineyard to rehearse with Ms. Adams and Mr. Shalhoub at their home, which they purchased 15 years ago.

Ms. Adams visited the Vineyard as a child and began renting in the summers with Lynne and friends 30 years ago. Mr. Shalhoub came for the first time in 1991, visiting Ms. Adams.

“I think I just fell in love with [the Vineyard] instantly when I arrived,” he said. “I remember flying in for the first time, and that was before the airport was renovated and changed . . . just a tiny little airport.” It was, he said, remarkably similar to the fictional airport on Nantucket he “worked” at in his role on Wings. During Mr. Shalhoub’s first few years visiting the Vineyard, people often joked that he was on the wrong island.

But the Vineyard was the right place. The couple and their friends stayed at the parsonage at the Whiting farm, where Mr. Shalhoub got to know both Ms. Adams and Josie better.

“It was a little family thing all of a sudden,” Ms. Adams said. The couple adopted their younger daughter Sophie after they were married. Sophie now lives year-round on the Vineyard; her boyfriend Devon is a local farrier.

The decision to buy a house here was nevertheless a bit of a struggle, given the time investment all homeowners must make.

“But I love having our own piece of the rock, I just do,” Ms. Adams said. The beaches of the South Shore are right across the road. Mr. Shalhoub took his first swim of the year, but it “was challenging,” he said. “Not like July and August when you can stay in for an hour.” The couple is often here through September and October, and spends Christmas in Chilmark. With Sophie living in the guest house and Lynne Adams in a house down the road, the “little family thing” has grown considerably.

“It’s starting to feel more and more like home, it really is,” Mr. Shalhoub said.

I Take Your Hand In Mine takes place Monday, June 30, at 7:30 p.m. at the Performing Arts Center at the regional high school. Tickets are $100 and $200 for center premium seating, and can be purchased at vineyardplayhouse.org.