Downhill skiing on Ochapowace began all the way back in the late 1960s. Four Saskatchewan First Nations, Sakimay, Cowessess, Kahkewistahaw, and Ochapowace, banded together to develop both the Last Oak Golf Club and the Last Oak Ski Area. Both properties were managed under the Last Oak Park Development Corporation, which was owned by all four nations. The ski area opened in 1968 and initially featured a very long rope tow and two ski runs. The hill was managed and run entirely by members of the four First Nations and it provided employment for many youth in the area.

In January of 1971, a federal-provincial agreement was signed. Its purpose was to provide financial backing to assist the economic development of the Last Oak ski area. As part of the plan, there would be three phases of development. Phase one would include the installation of two Dopplemayr T-bars and a new base lodge. This phase was financed mostly by the federal government, which paid $940,000. In 1972, a base-to-summit Dopplemayr T-bar replaced the long rope tow. A limited snowmaking system was also installed to help the resort in poor snow years, and the current base lodge was also constructed. In 1974, a second Dopplemayr T-bar was added which served beginner trails, and additional trails on the mountain were also built. Also in 1974, both the federal and provincial governments affirmed their intentions to spend up to $2.2 million on the development of the resort.

With the opening of its improved facilities, Last Oak exploded in popularity. Its slopes were by far the longest in Saskatchewan, and it drew many day skiers from the city of Regina. Over the 1970s, small improvements to the ski hill and the golf course were continually added, with all four First Nations continuing to manage both properties. The hill had its fair share of issues as well, as both the federal and provincial governments backed out of financing more developments. The hill also had problems with procuring enough water for effective snowmaking.

In 1983, the Last Oak Park Development Corporation consisting of the four First Nation bands was officially dissolved. Both properties went to whichever nation had the land they sat on. The ski hill was renamed from Last Oak to Ochapowace. The Ochapowace First Nation received a $400,000 grant which allowed them to undertake significant lodge renovations, cut four additional trails, and purchase additional snowmaking equipment. The Ochapowace First Nation continued to develop the ski area, and by 1988 the hill held Saskatchewan's only FIS-certified run, Eagle's Roost. Ochapowace broke several attendance records throughout the late 1980s, and the ski hill experienced significant popularity with local skiers.

In 1989, as part of a federal economic development program, Ochapowace received $800,000 from the federal government for ski area development. This money reportedly went to creating a new water reservoir for snowmaking and adding a second floor to the chalet. The Saskatchewan Economic Development Corporation also provided a $125,000 loan to Ochapowace, which was used to finance continued expansion of the snowmaking system.

Despite being involved in a long legal battle between the CRA and the Ochapowace First Nation, the ski resort continued operations in the 1990s. In 1995, a brand new Leitner-Poma quad chairlift was installed, which significantly increased the hill's uphill capacity.

Unfortunately, in the late 1990s and early 2000s, the Ochapowace First Nation invested very little into the upkeep and development of the hill as priorities for the band had shifted. Several fairly warm winters in the early 2000s cut into profit margins, and the hill operated sporadically during this time. By 2007, the band made the decision to halt downhill skiing operations at Ochapowace. The ski hill was completely shuttered for a number of years and the facilities deteriorated very quickly.

However, by 2015, the band expressed interest in reviving the ski area as a year-round destination. The lodge, which was in very rough shape, was completely rebuilt. In 2017, the quad chair received new chairs and was brought back to life. The band purchased a used water slide from Regina and also announced the installation of a zipline. Unfortunately, despite the money put into Ochapowace, nothing has really changed since then. Although the lodge is now used, there have been no recent developments at the ski hill. It is still a possibility that Ochapowace can reopen as a ski hill one day, however as the years progress, it seems somewhat unlikely that it ever will.