Original Ski Area

In the 1870s, a logging road was cut through the thick forest on the mountain now known as Hollyburn Mountain. The mountain was first ascended in 1908 by members of the Vancouver Mountaineering Club. By the 1920s and 30s, multiple ski clubs had established themselves there, and the Hollyburn Lodge was built there in 1926.

In 1948, a rope tow was built on the "Popfly" from the Hollyburn Lodge across First Lake, and on January 17, 1951, the Hollyburn single person chairlift was opened, bringing skiers from Hat Inn at the base of the mountain to the Highview Lookout at 850m elevation. It was designed by the Riblet Tramway Company, which brought prefabricated materials for the towers, the chairs, and the loading platforms. Hollyburners who had originally used a variety of logging roads to reach the ski area could now look forward to a 12 minute ride up the mountain. The Hi-View Lodge was also built beside the top of the chairlift. However the top station of the chairlift burned down in June 1965, along with the Hi-View lodge. It was believed to be intentionally set. ^{[5] [6]}

On November 23, 1963 a Royal Canadian Navy T-33 Jet crashed while on a training flight near the present day Sky Quad chairlift on Mt. Strachan, killing both pilots. In 2014, a memorial plaque was erected at the crash site. ^{[7] [8]}

Present-Day Downhill Ski Area

The present day downhill ski area was initially opened by BC Parks in January 1976, after two Murray-Latta double-chairs, the Green chair and the Black chair, were constructed on Mt. Strachan and Black Mountain. The Cypress Bowl road leading up to the resort had previously been completed the year before, at the cost of $13 million.

Cypress Bowl Recreations took over the resort in 1984, and Night skiing was added in 1985 on those two chairs. In 1987, the Sky Chair was installed at the peak of Mt. Strachan, opening up new terrain and reaching the highest point on either mountain. The chair was a Mueller double relocated from Apex Mountain Resort. ^[9]

Cypress was the first ski resort in BC to allow snowboarding, doing so on March 15, 1987.

Another double-chair, the Midway Chair, was installed in 1990 on the lower slopes of Mt. Strachan. In 1997, the original double chair on Mt. Strachan was replaced with a Poma fixed-grip quad, the Sunrise chair, following the same lift line. After Cypress was purchased by Boyne Resorts in 2001, the original chairlift on Black Mountain was replaced by the Eagle Express, a detachable quad chair built by Doppelmayr. Additionally, the rope tow in the beginners area was replaced with a fixed-grip quad chair, the Easy Rider Quad Chair.

In 2007, the Sunrise quad chair was replaced with the Lions Express Quad Chair, another Doppelmayr detachable quad chair. This reduced the ride time up Mt. Strachan by nearly half. The former Sunrise chair was moved across to Black Mountain and was installed on new terrain, which opened 9 new ski trails. This chair is now called the Raven Ridge Quad Chair. ^[5]

In 2022 Cypress closed the aging Sky Chair and built the Sky Quad, A fixed-grip quad lift with a loading conveyor belt. ^[10] The lift opened December 18, 2022 according to social media posts. ^[11] after delays due to a construction helicopter needing to conduct an emergency drop of a construction load due to unexpected sudden weather. No persons were injured during the mishap. ^[12]