Wintergreen is a four-season resort community spanning 11,000 acres on the eastern slopes of the Blue Ridge Mountains in Nelson County, Virginia. There are two residential communities made up of vacation houses and condos as well as full-time homes. One is Stoney Creek, located in the valley at an elevation of 800 feet. The other is the mountain community around the ski resort at an elevation ranging between 3,300 and 3,900 feet. 

The idea of a sporting club for valley and mountain property owners took life after an organizational meeting on Saturday, June 8, 2013 in Stoney Creek. Twenty-nine people attended,  27 full-time residents and two weekenders. A follow-up informational meeting was held on Saturday, July 13, 2013, when the club was launched. Karl Hess was the founding president.

After the discussions in these meetings and surveys of the community, the basic focus of the club was said to be:

  • Bringing people with common sporting interests together

  • Offering informational and educational opportunities

  • Introducing a variety of new sporting activities to members

  • Planning and coordinating sporting events and trips

Four primary "areas of interest" groups were formed: Archery, Boating, Fishing, and Shooting. In the summer of 2017, a fifth interest group, Biking, was added. Hiking, the sixth interest group, was added in 2024.

The Wintergreen Property Owners Association management has encouraged and advised the club's leadership. In addition to providing programs and events in each of the sports, the club is enhancing the WPOA properties, expanding the archery fields, and improving fishing in the WPOA-owned lakes by stocking and improving water quality.

Sporting-related events are restricted to WSC members. Starting in 2016, yearly membership dues were increased to $25 (from $10). The club's twice-annual general membership meetings are held in the spring and fall.

At the end of 2015, the membership was about 150; by 2017, about 300 people were active in the organization. In 2024, the membership numbered more than 500.