From historic trails and sternwheelers to winding mountain roads, Kelowna’s past is written across its landscape. Once part of the Hudson Bay Trail, routes like Westside Road and early wagon roads connected communities, while sternwheelers—the “White Queens” of Okanagan Lake—ferried goods, passengers, and even soldiers. Today, the legendary Tail of the Ogopogo continues to draw adventurers, curving along the lake’s edge where history and scenery meet.

Winding through history, the trail between Fintry and Nahun was once part of the Hudson Bay Trail, a vital connection between communities. By 1908, a rugged wagon road linked Westbank to Nahun, and by 1916, a horse-drawn road to Ewing’s Landing opened up travel to Vernon—no ferry required. During the Great Depression, workers from Wilson Landing’s relief camp helped shape what is now Westside Road, carving a safer path through Traders Cove.

For decades, elegant sternwheelers ruled the lake, ferrying everything from fresh produce and gold bricks to soldiers heading off to war. These adaptable vessels, known as the White Queens, made it easy to travel, deliver goods, and call for a ride—just a signal from shore and a searchlight in the dark would bring them in.

Sternwheelers That Once Sailed Okanagan Lake:
  • Aberdeen (1892–1913) – A 44.5m wood-burning steamer, later converted to coal.

  • Fairview (1894–1897) – Short-lived but efficient at 17m.

  • Okanagan (1907–1930s) – The largest at 59m, built for coal power.

  • Kaleden (1910–1920) – Compact at 28.6m, served for just a decade.

  • Sicamous (1914–1936) – The grandest at 61.1m, its final passenger voyage was in 1936.

Twisting and turning along the lake, Westside Road is as legendary as the creature it’s named after. Nicknamed "The Tail of the Ogopogo," its 330 curves and rolling elevation changes make it a favourite for road-trippers and motorcycle enthusiasts, much like the famed "Tail of the Dragon" in the Appalachians. Whether you're here for the ride or the view, this historic road is a journey in itself