The road was constructed in 1915 and financed by entrepreneur Spencer Penrose at a cost of approximately 500,000 US dollars. An earlier route, the Pike's Peak Carriage Road, had existed since 1888, opened by the Cascade Town Company and used by thousands of tourists before its closure in 1902. Penrose's new highway replaced it with a road capable of accommodating motor vehicles, and his motivation was largely promotional: he believed a motor road to the summit would attract visitors to Colorado Springs and support his planned resort hotel, The Broadmoor.
The highway was formally completed on 1 August 1916. That same year Penrose organised the inaugural motor race to the summit, establishing what would become one of the longest-running motorsport events in the United States.
From 1939 until 1947 the highway was designated Colorado State Highway 250 and maintained by the Colorado Department of Transportation. Since 1947 it has been maintained by the City of Colorado Springs. The road is at least partially open year-round, with access limited only at altitudes where snow removal becomes impractical. Tolls are charged per person rather than per vehicle, with adult and child rates varying by season.
For most of its history the upper portions of the Pikes Peak Highway remained unpaved, giving the mountain road its distinctive loose-gravel character and contributing to the risk profile of both casual driving and hillclimb racing. The unmetalled surface came under legal scrutiny in 1998 when the Sierra Club filed suit on grounds of environmental damage: an estimated 150 million pounds of gravel washed away from the road annually, the same volume that had to be hauled back up each year to maintain the surface. The runoff had filled alpine ponds and wetlands with gravel and deposited layers averaging two to four feet deep on the forest floor below.
Under the terms of the settlement between the Sierra Club and the City of Colorado Springs, the unpaved sections were to be converted to hard surface. Paving proceeded at a rate of roughly ten percent of the route per year beginning in 2002, and the project was completed on 1 October 2011. The 2011 Pikes Peak International Hill Climb was the last event to include any dirt sections.
Rod Millen, who had held the course record on the all-dirt road since 1994, warned at the time that paving would fundamentally alter and potentially end the hillclimb race. His prediction did not materialise: registrations for the 2012 event, the first run entirely on asphalt, exceeded 170 entrants by December 2011, compared with only 46 at the same point the prior year.
The Pikes Peak International Hill Climb, also known as The Race to the Clouds, has taken place on the highway every year since 1916, making it the second-oldest motor car race in the United States. The course uses 12.42 miles of the highway, rising 4,720 feet from the start at mile seven to the summit finish, with over 156 turns and grades averaging 7.2 percent.
A second racing event, the Pikes Peak Cycling Hill Climb, has also been held on the highway since 2010. The 2016 edition doubled as the inaugural USA Cycling Hill Climb National Championship.
A SNOTEL weather monitoring station operates near the Glen Cove Visitor Center at the 13-mile marker, situated at approximately 11,450 feet in the subalpine life zone. The road's extreme altitude range means weather conditions can shift dramatically between the base and the summit, and snow can close the upper sections at any time of year.