Big Baskets of the Bluegrass
July 19th, 2025 at The Bar Complex
Each year, the Kentucky Bourbon Bears present a charity raffle combined with an underwear fashion show — called Big Baskets of the Bluegrass. At this event, models show off their “big baskets” (wearing underwear) while carrying out big (raffle) baskets. Patrons are given numbered paddles to bid on the models’ baskets. The winner also gets the underwear the model is wearing!
Big Baskets of the Bluegrass is the 2nd largest annual fundraiser presented by the Kentucky Bourbon Bears. At our 2024 event – we raised over $5,000 for local LGBTQ+ charities. Since 2011, we have raised over 1/2 million dollars for local LGBTQ+ charities.






















