Downhill skiing at Cleary Summit dates all the way back to the 1940s. Back then, skiers would make the drive to the end of the highway to ski the current Cleary Summit area. Trips to this region were quite popular, and the first downhill ski races at Cleary Summit were actually held in 1941.

In 1949, Bob and Sylvia McCann as well as Link Imon leased the Cleary Summit land from the North Star Borough. They installed a 1,300-foot rope tow on the lower T-bar line that year and also built a small lodge, which burnt down in 1953. This prompted the construction of another small lodge, which would subsequently burn down in 1956. With the lodge rebuilt that year, a second rope tow above the highway was also added, opening up more terrain.

In the early days of skiing at Cleary Summit, the Steese Highway was only plowed to the ski resort. This facilitated top-to-bottom skiing over the highway, at least until more of the road became plowed later on. Cleary Summit quickly became the largest commercial ski resort in Alaska, drawing fair crowds every weekend. With 2,550 feet of elevation and built on a north slope, Cleary Summit usually was able to remain open until April when its competitors in the town of Fairbanks were not.

Alaska was thought of at this time to be the world's next big ski destination, which even brought French lift manufacturer Poma to Cleary Summit in 1958. In 1958, Cleary Summit incorporated as a public company and offered local Fairbanks residents the opportunity to purchase stock. Reportedly this was used to finance a new T-bar. While it was reported that the lift would be built by Poma, it was not. In August of 1959, construction of the new $36,000 T-bar was underway, which officially opened in December of 1960. This lift was truly the backbone of the resort, and though it was retrofitted by Dopplemayr a few years later, the original bones of the lift ran until closure.

In 1962, Skiland was built right beside Cleary Summit. For most of the life of Cleary Summit, Skiland was quite underdeveloped, boasting two rope tows and with a lodge built from a repurposed USSR mining camp building. It was also in 1962 that Cleary Summit's lodge went up in flames, started by a cigarette left on a fabric couch. The fire led to the building of the iconic Cleary Summit Lodge, which lasted far longer than its predecessors. Cleary Summit also installed a beginner J-bar serving the beginner slope.

Skiland closed for a number of years in the 1960s, leaving Cleary Summit as the only public option, as Birch Hill was military only. Cleary Summit thrived in this time, teaching countless kids how to ski and hosting countless races.

In 1972, Skiland reopened under new ownership. While the two mountains were in heavy competition, Cleary Summit was definitely the more built-up mountain. The lodge had a full restaurant which served wine and the lifts were all modern, while Skiland only boasted a shack that sold snacks and two steep rope tows. Skiland also heavily relied on volunteers to keep the organization running.

Modernization at Cleary Summit continued in 1972 when the resort replaced the upper mountain rope tow with a new Dopplemayr T-bar. By 1976, the J-bar had been replaced with a Dopplemayr platter.

Cleary Summit really didn't change much after the 1970s. While Bob McCann contemplated installing a used chairlift in 1986, he chose to pass, stating that the population was unable to support that kind of an investment. Instead, McCann chose to install a snowmaking system which was fed from a deep well. It was also around this time that Tom McCann took over operations from Bob McCann.

In 1991, Birch Hill installed a new Riblet double. Skiland also announced that they had purchased a $250,000 Müller double from SilverStar and intended to install it that year. This worried Tom McCann, who stated that the Fairbanks ski market was already oversaturated and that it couldn't support everyone. More bad news came for Tom McCann when the military allowed civilian access to Birch Hill in 1993. Additionally, Moose Mountain opened to the public in 1993 after years of negotiating with the city of Fairbanks.

It was in this environment that Tom McCann announced the closure of Cleary Summit in October of 1994. Razor-thin profit margins, rising insurance costs, aging facilities, and an abundance of competition spelled doom for Fairbanks' oldest ski hill. The upper T-bar and platter were sold to Hilltop Alaska, though only the platter was installed. The lodge sat vacant, surprisingly intact, until it was lit on fire and burned down in 2008. Today the ski trails sit remarkably preserved on the mountain, and much of the lower T-bar still stands as a testament and memento to the ski hill that started it all.