Horse races at the Tanglewood Steeplechase often attracted crowds in excess of 20,000 between the 1960s and 1990s. At the 1978 races, this owner shared a good laugh with his horse.
All told, the annual event was a major social affair and more than just a horse race as spectators would dress up in seersucker suits or fancy hats.
The Steeplechase 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.”