Howard Shaw grew up in Windsor, Nova Scotia. As a youth, he was very active in sports such as track and field, cycling, and gymnastics. In the late 1800s, he competed in many cycling races at track meets all over Nova Scotia.

After going on to Acadia University in Wolfville, Shaw became more involved in the training side of sports. In 1891, he competed in many sporting events at Acadia and was responsible for training the gymnastics team during the 1891-1892 academic year.