The Tanglewood Steeplechase was more than just a horse race. It was a major social affair.
From the 1960s to the 1990s, the event often attracted crowds in excess of 20,000. It was an opportunity not just to watch a horse race, but to dress up and be seen. There were men in seersucker suits throwing horseshoes and tapping kegs; women in fancy hats sipping sparkling wine and mimosas; tailgate spreads filled with ham biscuits, pimento cheese, caviar, boiled lobster, and Gulf Coast oysters. And, of course, there were horse races.
The event was organized in 1963 by local horse lovers and launched with pure intentions: Give locals a taste of big-time horse racing with a touch of Kentucky Derby elegance. While attendance soared for decades, it gradually dropped off after gaining a reputation for drinking and rowdy behavior. The last “original” steeplechase was held in 2002, though the event was briefly revived in 2010. Despite its fall from grace, the race is still remembered in a positive light, with many attendees hailing it as “the biggest party of the year.”