Squier's father, Lloyd, owned and operated WDEV in Waterbury, Vermont, and Ken began his on-air work at age 12 (when Lloyd Squier died in 1979, Ken Squier inherited the station and remains its principal owner and CEO). Squier's racing announcing career began when he announced a stockcar race from the back of an old logging truck at a tiny dirt track in Vermont at age 14. He was the announcer at Malletts Bay and the Northeastern Speedway as well as the Monadnock Speedway in the 1950s. In 1960 he opened Thunder Road International SpeedBowl, the Barre, Vermont, quarter-mile oval (sold in April 2017).