The Whippoorwill Festival was founded in the Spring of 2011 by Dave Cooper, a former mechanical engineer who spent 20 years working in industry, mostly designing and maintaining machinery.   He became involved in the anti-mountaintop removal campaign after meeting Larry Gibson, the "Keeper of the Mountains" from Kayford Mountain, West Virginia.  He wanted to envision a hopeful, post-coal economy for Appalachia, by sharing old time and sustainable living skills.

After 2017, the festival was run by a small but dedicated crew who kept it growing ad thriving until the pandemic hit in 2020.  After several years of dormancy, and with a new political landscape, Dave has revived the Whippoorwill festival in a new location north of Lexington, Kentucky.  

The Whippoorwill Festival was greatly inspired by Dave's experience with the non-heirarchal philosophies of Kentucky Heartwood and Mountain Justice.  After attending the Florida Earth Skills Gathering and the Firefly Gathering in North Carolina, he envisioned a new type of earth skills gathering that would blend environmental activism - like the important work of Kentucky Heartwood - with skill-sharing. 

Dave found Richard Louv's classic book Last Child in the Woods to be a profound call to all adults who care about the future of our planet to get children back playing in the woods and creek and trees.