The Podunk Bluegrass Festival was founded in the winter of 1995–96, by then Mayor of East Hartford, CT, Robert DeCrescenzo with assistance by recording studio owner Mike Hayden and musician/radio host Kevin Lynch.
Town officials, potential sponsors, and invited press were treated to a live bluegrass concert by a group of local musicians.
The official event kicked off on Friday, July 26, 1996, with a free bluegrass concert open to the public in the downtown park on Main Street.
The lineup of artists for the first Podunk Bluegrass Music Festival included John Hartford, Mac Wiseman, Laurie Lewis, Larry Sparks & The Lonesome Ramblers, The New Coon Creek Girls, Lost & Found, plus local CT band Northern Bound.
After a successful five-year run in Hebron, Podunk moved to its current location at the Goshen Fairgrounds in the Litchfield Hills of Northwest CT. Podunk has hosted many widely known bluegrass bands, including Kathy Mattea,[3] Ralph Stanley and the Clinch Mountain Boys, Doc Watson, Mac Wiseman, the Del McCoury Band, John Hartford, Vassar Clements, Jesse McReynolds, Doyle Lawson, Ricky Skaggs and Kentucky Thunder, the Lonesome River Band, Emmylou Harris, the Seldom Scene, Tony Rice, Tony Trischka, Sam Bush, Tim O'Brien, David Grisman, Peter Rowan, Dale Ann Bradley, the Kruger Brothers, Michael Cleveland, Rhonda Vincent and the Rage, the Gibson Brothers, Nickel Creek, the Steeldrivers, and dozens of up-and-coming local and regional bands.