Bloomington's Roots, Boots & Blues Fest is back for its second year on Saturday, Oct. 3, bringing eight hours of blues, roots music, old-school country and bluegrass to Upland Brewing Co.'s outdoor stage from 3 to 11 p.m. The all-ages festival closes out with headliner Cody Ikerd and the Sidewinders, backed by a lineup that spans veteran local blues acts and a busy vendor market.
According to The Bloomingtonian, organizer The Whirlwind Agency sent out the event announcement on Sept. 22, describing the day as eight hours of blues, roots, old-school country and bluegrass. Gates open before the afternoon performances begin, and music continues straight through to 11 p.m., per the same release. The festival will also feature more than 20 vendors along Shakedown Street, offering clothing, artist wares and community organization booths, while Upland Brewing Co. handles food and drink service on site.
A Lineup Built on Regional Blues Pedigree
The bill includes King Bee & The Stingers, Gordon Bonham, the Ladies Sing the Blues showcase and the Lazy Susan String Band, alongside additional afternoon performers. King Bee & The Stingers, founded in 2006 by Mark “King Bee” Menefee with his daughter Sarah Menefee taking over lead vocals in 2015, are three-time International Blues Challenge semifinalists in Memphis, according to King Bee & The Stingers. Their album Live from the Slippery Noodle was named a top-five finalist for Best Self-Produced CD by the national Blues Foundation in 2025, the band notes.
Gordon Bonham brings his own slice of blues history to the bill. Bonham, who moved to Bloomington in the mid-1980s and later played alongside members of John Mellencamp's band, formed the Gordon Bonham Blues Band in 1994 after founding the Cooler Kings, and performed at the 1995 grand opening of the Rock and Roll Hall of Fame in Cleveland alongside blues legends Robert Lockwood Jr. and Pinetop Perkins, according to Bonham's own account on his website. Joining him on keys is Craig Brenner, founder of Bloomington Boogies: The Bloomington Blues & Boogie Woogie Piano Festival, who has recorded and performed with national blues icons including Bo Diddley and B.B. King, per Craig Brenner's own biography.
Ladies Sing the Blues Brings Off-Broadway Credentials
The Ladies Sing the Blues set features vocalists Lauren Robert, Felicia Joi Cook and Bobbie Lancaster, with Robert bringing an especially deep theatrical resume to the Bloomington stage. Robert authored and starred in the off-Broadway music review .22-Caliber Mouth and has performed at national venues including CBGB, The Cotton Club and The Iridium in New York, as well as Kingston Mines in Chicago, according to Lauren Robert's own biography.
Closing out the night is Cody Ikerd and the Sidewinders, the Southern Indiana-based country-rock group that has performed across the Midwest and South for 11 years, according to their band biography. The band won Group of the Year – Outlaw Country in 2025 and Vocalist of the Year – Outlaw Country in 2024 at the Josie Music Awards, held at the Grand Ole Opry House in Nashville, Tennessee, according to Cody Ikerd Music.
Part of a Season-Long Concert Series
The Oct. 3 event is the autumn installment in a broader lineup The Whirlwind Agency has staged at Upland Brewing this year, following the Bloomington Bluegrass Fest in June, the Summer Soul Fest in August and, most recently, the Hippies and Cowboys Music Fest in September. That September festival ran on the same 3 to 11 p.m. schedule with the same vendor market layout, Hoodline previously reported.
Upland Brewing Co. opened its flagship 11th Street brewpub in Bloomington in 1998, a year after its founding, converting a former printing plant at 350 W. 11th St. into what has grown into Indiana's third-largest craft brewery by production volume. The campus includes a permanent outdoor limestone stage and The Wood Shop, a 6,000-square-foot sour ale barrel facility. Both the venue and the surrounding region take their name from the Indiana Uplands, an unglaciated 4,800-square-mile plateau in south-central Indiana recognized as an American Viticultural Area.
The festival series is co-sponsored by Bloomington public community radio station WFHB and local tourism bureau Visit Bloomington, which regularly partner with local organizers to promote live music and tourism in Monroe County. Upland's parent hospitality arm has also been expanding well beyond Bloomington: in May, Upland Hospitality acquired and refreshed Sangrita Grill & Cantina in Fishers, Indiana, part of a broader footprint that now spans Bloomington, Carmel and Columbus.
