The event was founded by Spencer Penrose, who had converted a narrow carriage road into the wider Pikes Peak Highway. The first race in 1916 was won by Rea Lentz with a time of 20:55.60, and the first Penrose Trophy was awarded that year. In the years following, Glen Schultz and Louis Unser shared a rivalry and won the event twelve times between them. A popular stock car class was added in 1929.
After World War II, Louis Unser extended his record, and the event was briefly part of the AAA and USAC IndyCar championship calendar. The Sports Car Club of America began sponsoring the race in 1953, triggering an influx of sports cars. Course records fell every single year from 1953 to 1962 — the longest unbroken streak of record-breaking runs in the event's history — with Louis's nephew Bobby Unser setting the majority of those marks. Motorcycle racing was also a recurring feature of the event from 1916 onward, though with interruptions; it became an established annual division only from 1991.
European competitors arrived in force from 1984. Norwegian rallycrosser Martin Schanche and French rally driver Michèle Mouton were the first Europeans to enter, with Mouton winning the Open Rally category in 1984. Mouton then set a new course record of 11:25.39 the following year for the overall victory. In 1987 Walter Röhrl won the event in a Audi Sport quattro S1 Pikes Peak with a time of 10:47.85.
The 1988 event produced one of the race's most celebrated runs: Finnish World Rally Champion Ari Vatanen completed the course in a turbocharged Peugeot 405 Turbo 16 in a then-record-breaking time of 10 minutes and 47 seconds, an effort captured in the award-winning short film Climb Dance directed by Jean-Louis Mourey and released in 1989.
The Pikes Peak Highway was originally a mix of gravel and asphalt sections. The City of Colorado Springs began paving the route in 2002 following a lawsuit by the Sierra Club over erosion damage caused by road gravel. The 2011 race was the last to feature any dirt sections, with the highway becoming fully paved from 2012 onward. Japanese driver Nobuhiro Tajima, competing with Suzuki, dominated the transition period — winning six overall titles between 2006 and 2011 and setting the first sub-ten-minute run in 2011.
The fully paved course dramatically accelerated record progression. In 2012 Rhys Millen set a new overall record in the Time Attack Division. In 2013 WRC legend Sébastien Loeb shattered the nine-minute barrier with a time of 8:13.878 in a purpose-built Peugeot 208 T16 Pikes Peak — a margin of improvement that rendered all previous records obsolete within a single event.
Electric cars appeared at Pikes Peak as early as 1981. From 2014 onward electric machinery took increasingly prominent podium positions, with Rhys Millen winning outright in 2015. The pivotal moment came in 2018 when Frenchman Romain Dumas drove the all-electric Volkswagen I.D. R to an overall record of 7:57.148, breaking the eight-minute barrier for the first time in the event's history and beating Loeb's 2013 benchmark by over fifteen seconds.
Motorcycles competed at Pikes Peak from the inaugural 1916 event, with the first winner being Floyd Clymer on a British Excelsior. The discipline faced long gaps in representation and serious safety concerns stemming from mass-start formats — incidents in 1976 and 1982 led to stoppages. A staggered wave-start system introduced from 1991 made the motorcycle competition viable on a permanent basis. The fastest ever motorcycle time was set by Rennie Scaysbrook on an Aprilia Tuono V4 at 9:44.963 during the 2019 event. Motorcycle racing at Pikes Peak came to a halt after four-time winner Carlin Dunne was killed in a crash on 30 June 2019; the competition was subsequently discontinued altogether.
The PPIHC accommodates a wide variety of machinery across multiple divisions. The premier Unlimited Division places no restrictions on vehicle type beyond safety inspection and general rules, and has historically produced the overall event winners. Further divisions include Time Attack 1 (production-based closed cockpit cars), the Porsche Pikes Peak Trophy by Yokohama (one-make Porsche Cayman GT4 Clubsport series introduced in 2018), Open Wheel, Pikes Peak Open (unlimited modifications on production vehicles), and an Exhibition Class for vehicles that fall outside sanctioned divisions but remain eligible for overall course records.
Pikes Peak is unique among major hillclimbs in the combination of extreme altitude, unrestricted vehicle engineering, and a course that has evolved from dirt logging road to all-paved racetrack within living memory. The race has served as a development showcase for turbocharging, four-wheel drive, and more recently electric powertrains, with each era producing landmark runs that redefined what was possible in hillclimb competition. The event continues to operate under the Pikes Peak Auto Hill Climb Educational Museum.