When I first started going to horse races, people didn't tailgate. You simply went to the race track, got some refreshments, socialized, and watched the races. These days, Keeneland Tailgates promise a full day of fun, complete with cornhole tournaments, elaborate food and drinks, and well-coordinated outfits. Oh, my, the outfits! Lilly Pulitzer dresses matched perfectly to bow ties. To party in a parking lot, y'all. I like to think of Keeneland tailgates as Kentuckians' answer to the SEC football tailgates that our friends in the deeper South so painstakingly plan.

HerKentucky has teamed up with Lifeguard Press to celebrate our birthday -- and the arrival of tailgating season -- in style with this gorgeous Lilly Pulitzer Insulated Cooler. Whether fall takes you to horse races, football games, or a weekend getaway, you can carry your drinks and refreshments in style!

You can enter to win using the Rafflecopter widget below. The winner will be announced Monday, September 30.

Good luck! And please let us know: Where will you be tailgating this fall?

a Rafflecopter giveaway