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).
Squier was among a group of six men who founded Catamount Stadium in Milton, Vermont, which operated from 1965 - 1987. He was a frequent announcer at this track dubbed "The Home of the Brave".
Squier co-founded Motor Racing Network in 1969. He announced races on the network for several years before moving to television in the later 1970s.
Squier served as a pit reporter for the very first live "flag-to-flag" coverage of the Greenville 200 on ABC in 1971 and he joined CBS Sports a year later.
Squier believed that people would watch the entire Daytona 500. "It was a tough sell," he said. "There was a general feeling that this was more of a novelty thing and that it wouldn't work on a national level." On February 18, 1979, CBS aired 1979 running of the "Great American Race" flag-to-flag. Television ratings were high, in part because a major snowstorm on the East Coast kept millions of viewers indoors. Richard Petty won the race, but a fight between Bobby Allison and Cale Yarborough made headlines throughout the United States.
For the next 20 years, beginning in 1981, various TV stations would get NASCAR coverage on various tracks: CBS, TBS, TNN, ESPN, ABC, and NBC. Squier would work for CBS and TBS over this time, covering half of the Winston Million races—the Daytona 500 and Coca-Cola 600.
Squier ended his career as a lap-by-lap commentary in 1997 and was replaced in the booth by Mike Joy. Squier had announced every Daytona 500 from 1979 to 1997. Squier became the studio host, where he remained until 2000. Squier was also present in the Fox Sports studio during pre-race and post-race coverage of Daytona Speedweeks and the 2001 Daytona 500, as well as the first-ever regular season Sprint Cup Series event televised by Fox.
On July 13, 2014, NASCAR on TNT broadcast its final race at the Camping World RV Sales 301. After the Pre-race show was complete, Squier said goodbye to NASCAR on TNT in this speech:
Hello everyone, I'm Ken Squier. And as the engines have fired at New Hampshire, I remind you that this is the final NASCAR broadcast for Turner Sports. I was the play-by-play announcer for TBS for 18 years. Beginning in the very first year of NASCAR coverage, 1983. It's been a real honor to be a part of today's broadcast, and I wish my colleagues the very best today on TNT. As this amazing, 32-year run comes to a close, I hope you enjoy today's race.
In September 2015, it was announced Squier would call part of the Bojangles' Southern 500 race as part of a throwback weekend for NASCAR to celebrate the years 1970-1974. Squier was joined by Ned Jarrett and his son Dale Jarrett. As part of the deal with Darlington with its throwback theme for the next several years, the trio called part of the race again in 2016 as the years 1975-1984 were celebrated. They returned in the same capacity for 2017.
Squier had a unique broadcasting style; he often described NASCAR drivers in his era as "common men doing uncommon things" and describing wrecks as "side over side, end over end" for flips and for calling wrecked racecars with the phrase "all torn up". A battle for position involving a large pack of cars would periodically be referred to as "an Oklahoma land rush." He was also known for the ability to switch between the "radio" style of broadcasting and "TV" styles. One of the biggest examples was the 1981 Talladega 500, when video went out and only the audio remained and he called the final laps when Ron Bouchard won.
Squier also announced CBS Sports' occasional CART IndyCar broadcasts in the 1990s as well as hosted the 1982 Individual Speedway World Championship from the Los Angeles Coliseum alongside four-time Speedway World Champion Barry Briggs of New Zealand and pit reporter Dave Despain. He has also announced in a wide range of sports outside of auto racing, including ice skating, golf, and tennis. He has announced outside of the United States, including Australia, Japan, and Europe. He was a play-by-play announcer for CBS' United States coverage of the 1992 Winter Olympics in Albertville and the 1994 Winter Olympics in Lillehammer. Since 2013, he is an announcer on the television show R U Faster Than a Redneck?.
Squier has acted in several movies, primarily as an announcer.The Cannonball Run (1981)
Stroker Ace (1983)
CMT 40 Greatest NASCAR Moments
Daytona 500: Drama, Danger, Dedication
He helped co-found Motor Racing Network, as well as his play by play announcing on the network.
President/Owner of Radio Vermont, Inc. and its radio stations WDEV, WLVB, and WCVT.
Co-founded World Sports Enterprises with Fred Rheinstein, the first) television production company to specialize in motorsports. It was sold to The Nashville Network in 1995 and to CBS in 1997. WSE was closed by MTV Networks.
Founder of Thunder Road International Speedbowl, Barre, VT. (Sold in April 2017.)
Founder of the American Canadian Tour late model racing series.
Former Co-Owner of Airborne Speedway, Plattsburgh, NY.
He is in the Oceanside Rotary Club of Daytona Beach Stock Car Racing Hall of Fame in 2000.
Squier is in the New England Auto Racers Hall of Fame in 2002.
He is a charter member of the Vermont Broadcasters Hall of Fame.
He was awarded the 2003 Smokey Yunick Award for his lifelong contributions to motorsports.
He is in the Vermont Sports Hall of Fame.
He is a member of the NASCAR Hall of Fame's Class of 2018.
Henry T. McLenore Motorsports Press Award – Journalism
Buddy Shuman Award, Motor Racing Network – Radio Race Coverage
E.M.P.A. Art Peck Award – Announcer
Eastern Motor Sport Press Association Award – Journalism
Vermont Sportscaster of the Year – 1963, 1967, 1969, 1973, 1997
Flock Award, Charlotte Motor Speedway – 1987