Barber developed an early passion for cars and began racing in 1958 while studying at Harvard University, where he earned a degree in English. His introduction to racing came at Lime Rock Park, and the circuit remained a constant throughout his career. His early club racing years produced rapid results: starting with an Austin-Healey Sprite in SCCA National competition, he progressed through a series of sports cars and formula cars into a sustained run of national championship success.
In the mid-1960s Barber won three consecutive SCCA national championships and finished third in the 1967 United States Road Racing Championship. He then won back-to-back Formula Ford National Championships in 1969 and 1970 — his 1970 title also brought the President's Cup and included 32 different lap records set during the season — a consecutive record that stood alone for many years.
At the start of the 1971 season, Barber purchased a March 711 under the Gene Mason Racing banner with the intention of racing in the US Formula 5000 series. Before shipping it across the Atlantic, however, he used it to contest Formula One Grands Prix: the Monaco Grand Prix, the Dutch Grand Prix, the Canadian Grand Prix, and the United States Grand Prix. He returned for the US and Canadian rounds in 1972. He subsequently raced GT cars before ending his active driving career.
When his driving career concluded, Barber acted on a conviction that was rare at the time: that auto racing was a coachable skill, learnable through systematic instruction just like any other sport. In 1975 he launched the Skip Barber School of High Performance Driving at Riverside International Raceway using two borrowed Lola Formula Fords and four initial students. The school was renamed the Skip Barber Racing School in 1976, and that same year he created the accompanying Skip Barber Race Series, which gave students a structured competitive ladder on equal machinery.
Over the following decades the school grew into the best-known racing school in North America. Its alumni include Indianapolis 500 winners Josef Newgarden and Alexander Rossi, NASCAR Cup Series drivers including Ross Chastain, and prominent names across multiple disciplines. The school also claims Michael Andretti, Hélio Castroneves, Bill Elliott, Jeff Gordon, Tony Kanaan, and Juan Pablo Montoya among its graduates. Barber divested from the racing school in 1999.
The school filed for Chapter 11 bankruptcy in May 2017 and was subsequently acquired by DeMonte Motorsports in December 2017. Under new ownership it resumed operations across its core programs — one-day, three-day, and advanced racing schools in both formula car and GT formats — at venues including Sebring International Raceway, Circuit of the Americas, VIRginia International Raceway, Road America, Watkins Glen, Laguna Seca, New Jersey Motorsports Park, and Lime Rock Park. The school also operates an esports program through iRacing. Its professional race team has competed in TC America and other series, accumulating over 35 victories.
In March 2024, the school announced the acquisition of the Superstar Racing Experience; however, the sale was reported to have fallen through by August of that year, resulting in SRX management filing a lawsuit.
From 1984, Barber owned and operated Lime Rock Park, a road-racing circuit in Lakeville, Connecticut. The circuit had been the location of his first racing experience and remained central to his motorsport identity throughout his career. In April 2021 he sold the facility to Lime Rock Group, LLC, retaining a minority stake. He lives in the nearby town of Sharon, Connecticut.
Barber was inducted into the SCCA Hall of Fame on 2 March 2013, and into the Motorsports Hall of Fame of America in 2025. A Skip Barber Racing School magnet famously appears on the refrigerator in the sitcom Seinfeld, reflecting the comedian Jerry Seinfeld's genuine attendance at the school and participation in several races.