1993--Roy Vines Theme: "Best in the West"
1994--Bea Neuman
1995--Bill Stimpson Theme: "The Cowboy Way"
1996-- Theme: Small town traditions
1997--Bob Schuyler Theme: Hometown Hoedown
1998--Norm Evans Theme: 100 Years of Western Tradition
1999-- Theme: Riding through the decades
2000 --Andy Pedro Theme: Starting Anew
2001--Don and Dorothy Emerson Theme: Boots and Spurs
2002--Eveyln Nelson Theme: She`s A Grand Ol` Flag
2003--Anna Peterson Theme: Celebrating the All American Small Town 2004--Delores Spooner Groves Theme: Western Ways for Western Days 2005--Ellen Hunt Theme: The Wild Wild West
2006--Lon and Anne Scott Theme: 45 Years of Pure Country
2007--Joyce Breland Theme: Back in the Ole West
2008-- Frank Parriott Theme: Beneath These Western Skies
2009--George Sweat Theme: Bits and Spurs
2010--Middletown Rancheria Theme: Spirit of the Old West
2011-- Larry Menzio Theme: 50 Years of Fun
2012--Bob Roberts Theme: Country Western Family Fun
2013 - Ellen Hunt Theme: Family Fun for Everyone
2014 - Phil & Betty Bickford Theme: Long Live Western Heritage
2015 - Harry & Rilla Krall Theme: Long Live Western Heritage
2016: Fred Waldon Theme: Long Live Western Heritage
2017: The Dennis family Theme: Shades of the Old West
2018 The Johnson family, Alyn & Paula
2019 - Millie Simon
2020 - No Middletown Days - covid
2022 - No pioneer award presented
2024 - The Weatherwax family