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 a 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.

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 at first: Archery, Boating, Fishing and Shooting. In the summer of 2017, a fifth interest group, Biking, was added. By 2017, about 300 people where active in the organization.

The management of the Wintergreen Property Owners Association encouraged and advised the club's leadership. Besides holding programs and events in each of the sports, the club is enhancing the WPOA properties, creating archery fields and improving fishing in the WPOA-owned lakes by stocking and enhancing water quality. Club members are actively investigating opportunities where WSC might work with area youth programs. 

WSC has also held successfully coordinated travel programs for its membership and more are planned.

Sporting-related events are restricted to WSC members. Yearly membership dues were increased to $25 (from $10) starting in 2016. The twice-annual general membership meetings are held on the first Saturday of May and the first Saturday of November. At the end of 2015, the club's membership had grown to over 150.

In 2016 Charles Batchelor's Addcontext launched a start-of-the-art website and digital communications platform to better serve the WSC membership and offer the expertise of its membership to the entire sporting community.

John Tani followed founding President Karl Hess as the club leader in 2016. Under Tani’s leadership, the membership in each of the four interest groups grew or remained healthy and biking was added. In October 2018 Tani’s term as president expired and Ron Cote’ took on the role for a two-year term.