Boston began racing at the age of seven before moving on to the World Karting Association two years later. By the time he was twelve years old, he was racing 80cc go-karts and mini-sprint cars. In 1995, Boston won the Rookie of the Year division in the Mini Sprint 800cc division at Miami County Speedway. He won the track championship at that track over the next two years.
In 1999, Boston moved to the Great Lakes Outlaw Sprint Series, a sprint car division based in the MidWest. He would go on to win several races over the next two years. Reid garnered more awards, the 2002 USAC Sprint Car Rookie of the Year, and the National Sprint Car Hall of Fame Non-Wing Rookie of the Year. He got his first win that year at Eldora Speedway.
He would go on to race in France as part of the Red Bull Formula One program, where he was signed to a sponsorship deal. In 2004, Reid signed a driver development contract with Hendrick Motorsports. He made his Busch Series debut later that year at Richmond International Raceway with NEMCO Motorsports, finishing 37th after a crash. He made two more starts that year. In 2005, he raced seven races for Hendrick in the Busch Series. His best race was at Nashville Superspeedway, where he started and finished seventeenth. Unfortunately, he was released from his contract at Hendrick at the end of the year.
In 2006, Reid will be a rookie in the Craftsman Truck Series circuit with a brand new team, Woodard Racing, which will receive support from Evernham Motorsports. Following the AAA Insurance 200, he has made every race and has three top-20s, with a best of 14th at Mansfield Motorsports Park.