Wintergreen Ski Resort

Wintergreen Resort traces its start to 1969, when developers purchased a roughly 10,000-acre tract in Virginia’s Blue Ridge Mountains known locally as “The Big Survey,” before opening the resort itself in 1975. Rather than building around a conventional base village, Wintergreen concentrated much of its lodging and amenities on the mountain’s own peaks and ridgelines, a “mountain top” layout that remains unusual among ski resorts on the East Coast, where base-area development is the norm.

Ownership has changed hands repeatedly since the 1970s, passing through Cabot, Cabot & Forbes, a Bankers Trust subsidiary called Melba Investors, businessman James C. Justice II starting in 2012, the real estate investment trust EPR Properties in 2015, and finally Pacific Group Resorts, Inc., which has run the property since 2021. Through those changes, the resort held onto at least one point of civic pride: it hosted the first Winter Special Olympics in January 1978, a distinction that predates most of its later corporate ownership transitions.

On snow, nine lifts, five chairlifts and four magic carpets, an unusually generous lift count for the resort’s size, serve 21 mapped runs across 8.64 kilometers of trail, dropping 301.8 vertical meters from a 1,066.8-meter summit to a 765-meter base. Advanced terrain leads the difficulty split at 3.54 kilometers, ahead of 2.87 kilometers easy and 2.12 kilometers intermediate, and the resort has long run night skiing across a large share of its terrain, letting visitors from the Richmond and Charlottesville corridor ski well after work hours end.

No multi-resort pass currently includes Wintergreen, so lift access runs entirely through the resort’s own tickets and season passes. Shenandoah Valley Regional Airport, 38.7 kilometers away, is the closest airfield, with Charlottesville Albemarle a similarly convenient option at 49.2 kilometers; Roanoke, population roughly 100,011, is the nearest larger city at 113.8 kilometers, while Richmond, considerably bigger at 226,610 residents, sits farther out at 136.3 kilometers. Beyond skiing, Wintergreen also runs an award-winning tennis academy with 22 courts, a program that predates much of the resort’s ski infrastructure and still operates as a year-round draw independent of snow conditions.

More than fifty years and five ownership groups on from the original Big Survey land purchase, Wintergreen’s basic bet, that a mountain-top resort model could work in the central Virginia Blue Ridge, has clearly held up well enough to keep attracting new owners rather than being abandoned or converted to a purely residential community. The repeated ownership changes are worth noting for anyone comparing Wintergreen to steadier single-owner resorts elsewhere in this dataset: real estate investment trusts and resort operating companies alike have all seen enough value in the property to keep buying it, even as skiing itself has never been the biggest driver of Wintergreen’s overall real estate and hospitality business. For a Richmond or Charlottesville family, that translates into a resort that functions as much as a broader mountain community with golf, tennis, and lodging as it does a dedicated ski destination, with night skiing across a majority of its terrain making it a realistic after-work option on a weeknight rather than only a full weekend trip.