Shepherd was born in
Keswick, Cumbria. His family moved to
Cartmel at the outbreak of World War II. His first motorcycle was a
Royal Enfield Bullet earned from a job doing a milk round with his father. He later moved to
Bradford where he served as an apprentice cabinet maker. Shepherd was a member of the
Royal Signals Motorcycle Display Team during his National Service. In 1956, Shepherd was persuaded to compete in the Isle of Man TT. He rode his own motorcycle to the dock in Liverpool and took the ferry to the Isle where, he finished in an impressive third place in the Clubmans Junior TT at the
1956 Isle of Man TT. Shepherd won the 1958 Junior Manx Grand Prix riding an
AJS. He scored a double victory at the 1962 North West 200 when he claimed first place results in the 350cc and 500cc classes. Shepherd's greatest success came when he joined the East German
MZ factory racing team led by their lead Development Engineer
Walter Kaaden, known for his groundbreaking work in
two stroke engine technology. Although MZ provided him with a motorcycle, the impoverished factory struggled to provide much support and, he competed while functioning as his own mechanic. Despite competing on a limited budget, Shepherd managed to win the season-opening 250cc
United States Grand Prix, held at the
Daytona International Speedway then, placed second to
Honda's
Jim Redman at the
Isle of Man Lightweight TT to finish the
1964 250cc world championship season in third place behind the powerful
Yamaha and Honda teams represented by
Phil Read and Redman. In 1964 when a resident of
Grange-over-Sands, Lancashire, England, he was allowed to keep his MZ 125 cc
single cylinder and MZ 250 cc
twin cylinder machines as part of his earnings due to currency difficulties with
East Germany. He offered these two MZ for sale through
Motor Cycle, a UK weekly magazine. Shepherd retired in 1965 after recovering from a head injury suffered in late 1964 when testing a
works Honda in preparation for the
1964 Japanese Grand Prix. He told
Motor Cycle's
David Dixon in June 1965 that – whilst he felt fully recovered – he no longer had the confidence to be a top-runner, and would not ride Hondas unless he could give the best possible performance. He died peacefully at Summerhill Nursing Home,
Kendal, Cumbria in July 2007, with a funeral service at
Cartmel Priory followed by cremation at
Lancaster. ==Motorcycle Grand Prix results==