In 1935, while Franklin D. Roosevelt was coping with the Great Depression, Weston-born architect Raymond Austin was putting the finishing touches on a playhouse that one New York critic would later call "the most beautiful theatre in New England." The first Weston Playhouse, a converted Congregational church facing onto the town green, was renovated through a generous donation from Mrs. Herbert Otis Bailey - and featured a brand new stage and a magnificent Greek Revival facade. The playhouse also received some help from Mr. Roosevelt via his WPA Federal Artists Program which sponsored then resident painter Roy Williams in his creation of four great theatrical murals for the Playhouse walls. The beauty of the town and its theatre building soon convinced Boston Conservatory teacher Harlan Grant that Weston would be an ideal place to assemble a professional summer stock company.

Grant successfully pitched his idea to Weston's Theatre Committee (now headed by Raymond Austin) and, in 1937, the first professional summer season began, opening with Noel Coward's Hay Fever featuring a young actor named Lloyd Bridges.

Through the 40's and 50's, the company not only kept up a hectic schedule of ten new productions each summer, but added overnight "tours" of these productions to Woodstock (and briefly Rutland, Manchester, and even Burlington). In the late 40's, the Weston Community Club, which already owned the theatre building, acquired a second building next door where players were put up and a prototype light entertainment called "The Cellar" was held after the shows.

During the early morning hours of July 12, 1962, an overheated glue pot in the scene shop changed everything. A devastating fire engulfed the Playhouse and the building next door, destroying props, settings, costumes, and lights. In true show business fashion, however, that evening's scheduled performance of Write Me A Murder went on in a tent on the schoolhouse grounds, and , while the season continued, the plans for rebuilding began. The local community, responding overwhelmingly to the loss of its theatre, quickly raised funds to build a new $150,000 combined theatre and community center. Raymond Austin, serving once again as an architect, was able to raise the new Weston Playhouse (with its Greek Revival facade fully restored) in time to open the 1963 summer season with The Fantasticks . Meanwhile Harlan Grant continued to direct high quality productions in one of the Straw Hat Circuit's most spacious and attractively designed playhouses until his retirement in 1971 after 34 full seasons.

In 1972, Walter Boughton, Chairman of Amherst College's Drama Department, became only the second director of the Playhouse company. He promptly expanded the Playhouse repertory to feature musical theatre more prominently, and he instituted the popular after-hours revue, the Act IV Cabaret. Boughton also had to contend with his share of natural disasters. In June of 1973, and again in August of 1976, the West River overflowed its banks, running through the lower levels of the Playhouse - and wiping out much of the theatre's stock. In addition to causing Playhouse damage, the flooding washed away the bridge to Londonderry and many sections of the road, severely restricting audience access to the town. Still the show went on as before, and by the 1980's, the Weston Playhouse, now with a restaurant and cabaret to complement its mainstage productions, had become one of New England's most successful summer stock operations.

With Walter Boughton's untimely death in 1988, three of his long-time directors, Malcolm Ewen, Tim Fort, and Steve Stettler, pooled their collective forty-plus years of Playhouse experience to become a management triumvirate. Concerned at the mounting cost of running a high quality professional operation which now included talent from Broadway and Hollywood, the producing directors turned the Weston Playhouse Theatre Company into a not-for-profit organization for the first time in 1989.  Under Ewen, Fort, and Stettler, the Playhouse has redefined its role as a professional regional theatre, expanding its offerings beyond the traditional summer months and creating outreach programs which can serve Southern Vermont audiences on a year-round basis. Thanks to the dedication and generosity of its Board of Directors, Theatre Associates, community volunteers, patrons, company members and alumni, the theatre completed a $2 million capital campaign in 2002. The campaign secures the future of the Weston Playhouse with the establishment of a major endowment, the purchase and renovation of property for artist housing and rehearsal space, and capital improvements to the Playhouse facility including air conditioning and an infrared listening system. With an eye to the future and unparalleled support from its extended family of theatregoers and artists, the Weston Playhouse continues to build on the tradition of quality entertainment and community involvement which has characterized Vermont's Oldest Professional Theatre from its inception.