The Westport Country Playhouse’s new season will make you cry, laugh and sit at the edge of your seat with five shows that include musicals, dramas and comedies. The theater’s 88th season runs May 29 through Nov. 17.

“The 2018 season provides a rich variety of experiences for the Playhouse theater-goer,” said Mark Lamos, the playhouse’s artistic director. “It commences with Pearl Cleage’s suspenseful, powerful, and ultimately joyful Flyin’ West — the story of three women on the American frontier — and finishes with the world premiere of a moving new play — about families torn by the effects of a school shooter’s crime — called Thousand Pines by Matthew Greene.”

“Audiences will experience the stirring classic musical, Man Of La Mancha, as well as A Flea In Her Ear, [Georges] Feydeau’s madcap comedy of marital mishaps, and Theresa Rebeck’s comedy, The Understudy, about movie stars who take on stage roles, and their effects on actors,” Lamos added. “We’ll also be bringing back, by popular demand, Mona Golabek’s thrilling The Pianist Of Willesden Lane. It’s a season rich in emotion, stories by and about women, with the participation of a diverse and exciting collection of theater artists.”

Flyin’ West, running May 29 to June 16, is directed by Seret Scott. It takes place in post-Civil War era 1898 in an all-black town in Kansas, a haven for former slaves. The play follows a family of sharp-witted women who bravely overcome huge odds to escape their past.

Scott said, “Flyin’ West is both timely and timeless. In 1898, four pioneering black women, escaping the subjection of the South, travel west to Kansas and carve a life for themselves out of the unforgiving wilderness. Their trials, hope and above all, courage, create a history and legacy that we modern pioneering women still honor today.”

A new take on A Flea in Her Ear is written by David Ives. Taking the stage July 10 to 28, this comedy is co-produced with the Resident Ensemble Players at the University of Delaware. Raymonde is a turn-of-the-century Parisian housewife who wants for nothing — except for an amorous husband. Assuming he is unfaithful, she listens to the “flea in her ear” and a confusing roller coaster of accusations and mistakes ensues.

Lamos, who directs this play, said, “This exhilarating study in silliness was written by the master of French farce, Georges Feydeau, at the beginning of the creation of silent films — many of which were inspired by just this sort of madcap humor.”

The Understudy, written by Theresa Rebeck and directed by David Kennedy, will run Aug. 14 to Sept. 1. Sometimes what happens backstage is more entertaining than on stage. As audiences arrive for a play helmed by a Hollywood action star, the understudy is suddenly forced to take his place as things go awry backstage and tensions rise.

Kennedy, who is also the playhouse’s associate artistic director, said, “The Understudy is a delightful comic confection and a provocative exploration of the million minor humiliations that come with a life in the theatre. Making playful homage to Franz Kafka — one of the giants of 20th-Century literature, and a personal favorite of mine — Theresa has crafted a brilliantly funny play about art, celebrity, and the power of money to warp any creative endeavor.”

Man of La Mancha, written by Dale Wasserman and directed by Lamos, will run Sept. 25 to Oct. 13. The Tony-winning play comes to life here in a vivid journey with Don Quixote as he tilts at windmills and battles for good and the love of his fair maiden Aldonza. Lamos says, “The thrilling score and the inspiring message have made this one of the most popular musicals of all time.”

The season ends with the world-premiere Thousand Pines, written by Matthew Greene and directed by Austin Pendleton, Oct. 30 to Nov. 17. The drama, exploring the aftermath of a school shooting, debuted in 2017 by the Playhouse’s New Works Initiative and brings home the national dialogue about gun violence.

The playwright said, “The families portrayed in Thousand Pines are lost. But in the midst of this darkness they learn a lesson that I think resonates with all of us: the only thing we can cling onto in these times of extreme crisis is the people we love.”

A post-season bonus will be The Pianist of Willesden Lane returning for a special engagement Dec. 5-22. In the musical set in 1938 Vienna, a 14-year-old piano prodigy’s dreams of becoming a concert pianist are threatened by impending war in Europe.

The Westport Country Playhouse is at 25 Powers Court. For information visit, or 888-927-7529.