Two Planks and a Passion, a Nova Scotia touring Theatre Company, appeared in an article in the Globe and Mail in the winter of 1999. With a love for the theatre, a need to entertain guests in the evening at a large resort, and an interest in adding to the culture of the Ingonish area, Ian Green invited them to perform in a small theatre on the property. From this germ, the idea of developing a season of theatre for the visitors and residents of the area was sown.

Growing the theatre season was gradual and began to diversify when staff were sought out to perform in an amateur comedy production for the guests. Other professional companies followed and the next year a full season of amateur and professional productions was slated. Our audiences grew, as did the reputation of the productions mounted. The theatre flourished under the sponsorship of the Keltic Lodge and Mr. Green as its manager.

In the winter of 2002 another amateur theatre group was formed for the children of the area, performing the beloved musical Fiddler on the Roof. The response was overwhelming to auditions and 25 young people were chosen to participate. After this first performance the word in this small community was out and people were traveling a long distance to see the production. Annie Jr. followed in 2003.

Theatre on the Hill was born.