The original inhabitants of this Central Okanagan region were the Interior Salish people, who harnessed the area's natural resources and followed seasonal cycles of food gathering, hunting and ceremonial life. Missionary Father Pandosy settled in this area in the early 1860s, pre-empting land near Mission Creek, which was to become one of the Valley's largest farming operations. The settlement was later to be called Kelowna, meaning Grizzly Bear in Indian dialect.

Early pioneers focused on cattle ranching, an industry that fed the Cariboo gold miners and other early settlers. With a new rail line reaching Okanagan Landing at the head of Okanagan Lake, a brand new town site was laid out in 1892, spurring immediate growth in the region.

Kelowna was incorporated as a city in 1905 with a population of 600 people, and continued to experience moderate growth through both the First and Second World Wars. In 1925 the Canadian National Railway linked Kelowna to the outside world, facilitating the shipment of fruit and other goods.

The opening of the floating bridge by premier W.A.C. Bennet and Prince Margaret in 1958 paved the way for unlimited expansion of Kelowna, which still continues until today.

More recent historical items are worth noting as well:

• On August 6, 1969, a sonic boom from a nearby air show produced an expensive broken glass bill while at least 6 people were injured.
• In both 1986 and 1988, alcohol-fuelled riots erupted during summer Regatta festivities.
• On May 7, 1992, a forest fire consumed 60 hectares of forest on Mount Boucherie in West Kelowna; no homes were damaged.
• In August 2003, a nearby wildfire destroyed over 200 homes and forced the temporary evacuation of approximately 30,000 residents. During the 2003 fire, many trestles of the historic Kettle Valley Railway were destroyed. One of the trestles, Trestle 18, has been rebuilt, and other trestles are planned to be reconstructed as well.
• In May 2005, Kelowna celebrated its Centennial, marking 100 years of institution!.
• In 2005, construction of a new bridge to replace the Okanagan Lake Bridge began, all being part of a plan to try and alleviate the severe traffic problems experienced during the summer months (the height of tourist season).