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Derby Day
From top hats to boaters

When the Yale crowd talked of going to Derby Day in the 1920s, 1930s, and 1940s, they did not mean the horse races at Churchill or Epsom Downs. Instead, Yale’s premier social event of the spring focused on the boat races in nearby Derby, Connecticut.

For more than a quarter-century, Derby Day was a spring fling of revelry and abandon—too much abandon. By 1951, the event had fallen into disgrace due to the heavy use of alcohol and was abolished. But there remain lingering memories of a Derby Turnpike clogged by caravans of open cars and trucks that were filled with young men and women in formal wear, informal Gay Nineties dress, or country togs.

In the early 1920s conditions were right for inaugurating a Yale tradition. After years of searching for a good boat-racing venue near New Haven, the University selected a site on the Housatonic River at Derby in December 1915. But plans for building a boathouse had to be postponed until after the war, and it was not until 1923 that construction began.

A new crew coach, Ed Leader, brought a winning system and style that gave Yale its first sweep in eight years. Then it was announced that the spring regatta with Columbia and Penn, held on the first Saturday in May at about the same time as the Kentucky Derby, would now be held in Derby. Mardi Gras-like costumed parades by student clubs and alumni at reunions were already in vogue, and an opportunity presented itself for showing off theatrical high jinks.

Saturday, May 5, 1923, began with much posing and picture taking on campus. However, instead of going to the races in New Orleans-style costumes, the juniors decided to emulate the formal dress of the English Derby. They wore cutaways, top hats, and spats, and they sported canes, boutonnieres, and monocles. The seniors, wearing sailor suits, drilled in Branford Court under the command of one senior dressed as the “Ruler of Queens Navee” until the band and a special trolley arrived.

There were several means of transport to Derby. Some of the juniors rented horse-drawn carriages. In addition to the Trolley Express line that ran from the campus past the Yale Bowl and out the Derby Turnpike, there was also the New Haven and Derby Railroad. By 1926, a special train also came from New York to connect with the Derby Line. At the Derby railroad station, a 34-car observation train waited to take thousands of spectators along the riverbank. The juniors had their own special formal-wear-only car. Automobiles and carriages could follow along the roadway.

Events began on Friday when guests arrived for tea dances at the Sheff houses. Bands played for elegant suppers and on until the wee hours. Then, after students and their dates caught a few hours of sleep Saturday morning, it was off to the races.

In marked contrast to the sedate juniors, the seniors dressed as cowboys, Indians, and as Girl Scouts carrying signs that read, “The girls of today will be the mothers of tomorrow.” In 1924, some students put on a pantomime exhibition for those marooned in the observation train that had to wait an hour for high winds to calm down. The long train finally pulled out of Derby station and crawled up the river past the boathouse, the grandstand built near the finish, and in between the thousands gathered on the bluffs on either side. Some of the brave even took to canoes to get a better view of the finish.

More parties followed on Saturday night. The press proclaimed that Derby had come into its own as “the best place in the United States to view a race and second to none for rowing.”

When Yale won on Derby Day, the top hats and cutaways suffered heavy casualties, and throughout the 1930s the juniors lost interest in heavy formal attire. After the 1939 race, rowing reporter Tom Mendenhall '32, ‘38PhD, commented that “sartorially speaking, the trend was away from the top-hatted, tailcoat and fawn-trousers formalism of previous years towards a revival of the Gay Nineties tradition of peg-top trousers, club ties, blazers, and the ubiquitous boater.”  the end


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