Tremont made his debut in the Juvenile Stakes at Jerome Park on May 29, 1886, in a field of fourteen. In the absence of starting gates, the horses milled around the starting area for nearly an hour, during which time one colt was injured and had to be scratched. When the field was finally released, Tremont got a running start and went to the front. He led by three lengths at the top of the stretch, then opened a lead of six lengths when briefly given his head by jockey Jim McLaughlin.