Heather Richardson has competed extensively in both the hunter and jumper ring, and ended her junior career at Virginia Intermont College by qualifying for and competing in the 1996 Prix des States for Zone 7.

Prior to earning her degree, she rode and trained under Lyn Owens and Jimmy Cantwell. Following graduation, she worked for Kat Mulkey in Atlanta where she was responsible for teaching, taking clients to horse shows, and breaking and training show hunters. While there, she rode with Ann Kenan of Hunter Hill Farm.