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After almost four decades, the Newfoundland and Labrador Folk Festival has evolved from a one-day, 100-person event highlighting folk music performers of rural Newfoundland to a large-scale, three-day event that draws major acts from the mainland and beyond. Staged by the Newfoundland and Labrador Folk Arts Society, a St. John’s–based charitable organization, the festival is increasingly faced with the realities of growth and the challenges of fulfilling the organization’s place-based mandate as the festival widens its scope. Part of this challenge is the simple logistics of festival planning and funding realities. Drawing on my experience with the organization, this paper examines the course of that growth and the realities of organizing a large-scale outdoor event with a not-for-profit approach, as well as the challenges, both cultural and practical, of performing Newfoundland on the folk fest stage.