Trinity's Soap Box Derby is a traditional (though inconsistent) race down Vernon Street during Senior Week. Students were required to construct their own vehicles to ride in, the constraints being that the vehicle must have had brakes, at least three wheels, and propelled only by gravity.

The first derby was hosted in 1956 by the Interfraterity Council, with the racers representing the different fraternities. Future derbies were sponsored and aimed to raise money for charity; in this case an underprivileged child in the Hartford Soap Box Derby that year. In 1985 the money went to the Muscular Dystrophy Association.

Later derbies were organized and held by single fraternities, but participation was not limited to fraternity members. Vernon Street was closed off by police during the derby and vehicles were inspected prior to the race to ensure the safety of both the racers and the onlookers. The derby was held fairly consistently during Senior Week from its debut in 1956 up until the late 1980s, but seemingly has not been reported as happening since 1987.

The Trinity Tripod, 04/21/1987.

The Trinity Tripod, 04/23/1985.

The Trinity College Bulletin, May 1965.

The Trinity Tripod, 03/07/1956.