Prior to European arrival, local Indigenous peoples camped near Boggy Creek and used the butte as a lookout point.

Pilot Butte's early development was more substantial than neighbouring settlements thanks to its brick plants, sand and gravel deposits, and location on the Canadian Pacific Railway mainline.

The community incorporated as a village in the early 20th century; however, following World War I, most of its residents and buildings, including a hotel, train station, and water tower, were dismantled or destroyed.

Pilot Butte hosted the Western Canadian Softball Championships in 2002[7] and an annual rodeo has attracted visitors to the town every summer since 1993.

[16] Beginning in 1874 at Fort Qu'Appelle, Treaty 4 was signed between the Queen Victoria and various First Nation band governments, with its coverage spanning the Pilot Butte area.

[7] By 1882, the Canadian Pacific Railway had made its way through the District of Assiniboia; between Pilot Butte and Regina a crew set a company record for the most track laid in a single day.

[17] With the construction of the railway through the region, the community was established and the area's sand and gravel deposits were extensively utilized.

[7] In the following years, as settlers began farming in the district, Pilot Butte developed, with the name being chosen in 1883 to mean "lookout point".

[18] The origin of the name is derived from the flat-topped hill located in the community that served as a lookout for hunting buffalo.

[19] Because of Pilot Butte's location on the Canadian Pacific Railway mainline, significant settlement took place between 1880 and 1900, and a second brick plant began production in 1900.

[20] The settlement had grown greatly since its founding; a post office opened in October 1903, and in 1913 Pilot Butte was incorporated as a village.

[7] With automobiles allowing for easy transport to Regina, Pilot Butte began to lose its population—a trend that would continue for years.

[7] In 1946, the Pilot Butte Memorial Hall was opened; Premier Tommy Douglas was in attendance and spoke at the ceremony.

[7] Towards the end of the decade, the water tower was destroyed and construction began on a village office on Railway Avenue.

[6] Construction was completed on a new water treatment and sewer disposal facility in 2014, which saw the town win legal dispute with residents who protested the project.

[12] In 2018, a diverging diamond interchange opened on the Pilot Butte access road as part of the Regina Bypass project, only the second of its kind in Canada.

[10] Pilot Butte experiences a dry humid continental climate (Köppen: Dfb) in the NRC Plant Hardiness Zone 3b.

[27] Pilot Butte has warm summers and cold, dry winters, prone to extremes at all times of the year.

[43] The most commonly identified ethnic or cultural origins in Pilot Butte in the 2021 census were German (915 or 34.8%), English (715 or 27.2%), Scottish (505 or 19.2%), Irish (455 or 17.3%), and Ukrainian (420 or 16.0%).

[46] The town hosts the Annual Pilot Butte outdoor rodeo on the third weekend of June every year since 1993, complete with cabaret featuring current country headline musicians.

[18] Since 2020, Pilot Butte has been home to a drive-in movie theatre, which is located directly north of town on the rodeo grounds and is only one of few in the province.

[49] Also near Pilot Butte are various golf courses, including Westfalia, Green Acres, Murray, and Tor Hill.

[6] Today, Pilot Butte is home to a post office, school, church, library, gas station, and various restaurants and manufacturing plants.