This summer, the Martha’s Vineyard Playhouse is bringing back two productions that sold out last year: Miss Maybelline’s Nocturnal Flights of Fancy and the musical Billy Baloo.

Both plays were written by Islanders. Miss Maybelline’s Nocturnal Flights of Fancy is by Kathleen McGhee Anderson of Oak Bluffs and Billy Baloo is by Jemima James and the late Michael Mason of West Tisbury, whose son Willy Mason will return in the title role.

Jessie Pinnock, who played Laura in last year’s Billy Baloo production, co-stars with Mr. Mason as Ada, with Jonathan Lipnick and Paul Munafo returning as mountain miners in the Gold Rush-era tale, which opens August 22 and closes Sept. 14.

Unlike last year, when Billy Baloo was held over for extra performances, that won’t be possible in September due to the actors’ other commitments, said playhouse artistic and executive director MJ Bruder Munafo, who is directing the show.

Playhouse executive director MJ Bruder Munafo also directs Billy Baloo production. — Ray Ewing

Last year’s two staged readings of Miss Maybelline’s Nocturnal Flights of Fancy, a story about Black life on Martha’s Vineyard across generations, starred stage and screen actor S. Epatha Merkerson, who Ms. Bruder Munafo said was booked for other work this summer.

Ms. Bruder Munafo said she is still casting for Miss Maybelline’s, which runs from July 13 to August 10 and will be accompanied by an exhibition of Harry Seymour’s paintings and poetry in the playhouse lobby.

The summer season opens May 15 with the New England premiere of To Fall in Love, a two-hander from Theatre Lab, the professional theatre company at Florida Atlantic University in Boca Raton.

The award-winning play brings together a couple whose marriage failed after a family tragedy, as they spend one night together seeking to discover whether it’s possible to reclaim their relationship.

Written by Jennifer Lane, To Fall in Love is directed by Louis Tyrell and stars Niki Fridh and Matt Stabile. It runs Wednesdays through Saturdays at 7 p.m. and closes May 25.

Kathleen McGhee Anderson returns with her play Miss Maybelline's Nocturnal Flights of Fancy, opening June 13. — Courtesy Martha's Vineyard Playhouse

June brings two very different solo performances to the playhouse stage: Tyrone Davis, Jr.’s The Lesson and John Pielmeier’s Courage, based on the life of Peter Pan author J.M. Barrie.

Mr. Davis last appeared at the Martha’s Vineyard Playhouse in 2007, Ms. Bruder Munafo said.

“He kind of started his career here after college … and before you know it he was off Broadway and on Broadway,” she said, adding that Mr. Davis played Donkey in the original national tour of Shrek and now attends the Union Theological Seminary.

In The Lesson, playing June 7 and June 8, he plays all of the characters in a school community roused by a classroom incident, Ms. Bruder Munafo said.

Mr. Pielmeier — a playwright and actor known for writing Agnes of God — plays just one character in Courage and depicts his deep exploration of Barrie’s life and the experiences that shaped the Scottish author’s stories. Courage plays June 14 and June 15.

The Monday Night Specials — live readings of new plays by Island and Island-adjacent authors — will include a play by Marty Nadler June 10 and one by Kate Feiffer later in the month, Ms. Bruder Munafo said.

On July 6, the playhouse takes over the Martha’s Vineyard Performing Arts Center in Oak Bluffs for a fund-raiser with Celebrity Autobiography, a show that lets audiences hear the stars’ own words first-hand. The celebrities for this event have not been named yet, Ms. Bruder Munafo said.

This summer’s Shakespeare play at the Tisbury Amphitheatre is Much Ado About Nothing, directed by Mac Young.

A 16th-century comedy that loosely inspired the recent movie Anyone But You, Much Ado About Nothing plays July 18 through August 10.

“It’s a romp,” Ms. Bruder Munafo said.

For tickets and more information: mvplayhouse.org.