Terry Peak Ski Area began originally with the Bald Mountain Ski Club in 1938, with the installation of a rope tow for club members. Slope grooming in these early days was undertaken by club members hiking up and down the hill with their skis on in order to pack down the snow.

Many of the founding members of the Bald Mountain Ski Club left the area to serve in World War II. Ed Keene, who was one of the founding members of the club, returned from serving in World War II with the 10th Mountain Division, and initiated the start of what is now known as Terry Peak Ski Area.

In 1952, Ed Keene, Ken Keller, Ken Stormo, John Finola, and Richard Morcom formed the Black Hills Chairlift Company. The Ringer Chairlift was installed, but was originally used only for summer business. In 1954, the Black Hills Chairlift Company began operating the chairlift for winter ski business.

In 1967, the Ringer Chairlift was replaced by the Blue Chair (#1). In 1975, the Empress Chair (#2) was installed and in 1978, the Surprise Chair (#3) began operating.

Development continued during the 1980's with the installation of the Stewart Chair (#4) in 1985, which replaced the two surface Poma lifts. The new Blue Chair (#5) was needed in 1986 to eliminate the growing lift lines at Terry Peak. In 1996, the Beginner Chair (#6) was installed specifically for ski school classes and beginner skiers and snowboarders.

Snowmaking was introduced to Terry Peak in the 1970's to ensure a reliable snowpack during the Black Hill's unpredictable winters. Snowmaking improvements have continued up through present day, with a coverage of 60 percent of the slopes. In the summer of 2002, Terry Peak aquired 3 wells and 3 holding ponds as part of the reclamation at the the Golden Reward Mine. The recent aquisition gives Terry Peak over 14 million gallons of water storage for snowmaking.

The Stewart Day Lodge was built in 1988, replacing the old lodge, 2-K Bar and ski school buildings. In the summer of 2001, a 3,000 square foot sun deck was added to the lodge.

In 1999, the Black Hills Chairlift Company approved a five-year plan for major improvments at Terry Peak Ski Area, beginning with the installation of the Kussy Express high-speed detachable chairlift, replacing Chairs #1 & #5. The Surprise Express high-speed detachable chairlift was installed in the summer of 2002, replacing the old yellow chair.

Heading into the 2004/2005 season, Terry Peak began the largest terrain expansion in over 25 years. New trails that were developed include North Side Glades, Ben Hur Glades, Maringo, Missing Link and lower Black Moon. The expansion is approximately 100 acres and accomodates the intermediate to expert skier and rider. The project will continue for the next couple years.

Maringo was publicly skied for the first time on December 30, 2005. The next day, Missing Link and North Side Glades opened to skiers and riders, offering a new downhill experience unlike anything else in the Black Hills.