During the spring of 1927, Mr. and Mrs. Edward Goodman, devotees of the performing arts, were able to interest a number of Dorset residents in producing a play. In April 1927, a three-act play entitled ’39 East’ was presented in the Dorset Town Hall for the benefit of the PTA and was received with great enthusiasm. From this, a movement took off. Many summer residents and artists in town formed a group, the Dorset Players, who would continue performances for the town. They realized that the space in Town Hall was not suitable nor permanent enough for the goals of the group. May Goodman purchased land at the edge of the village and the group held two years of performances in nearby towns to gather funding to erect a playhouse. Ernest West, a member, offered two barns on his property in town and it, plus one more barn, were incorporated into the new playhouse. The auditorium was built so that the weathered sides of the barn boards were on the inside and hand hewn timbers 12 by 12 inches were used to achieve a rustic effect which draws many favorable comments from those visiting the Playhouse. It remains a cultural center of the town and greater region to this day.
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