Wintergreen Resort opened for skiing on December 20, 1975
Of the 16 speakers at the program on January 11, 2025, who shared their memories of Wintergreen over the last 50 years, three talked about how the resort’s beginnings has shaped what the resort community has become.
The 10-minute video below featuring LF Payne, Tim Hess, and Jay Gamble is excerpted from the 90-minute video of the entire meeting at the bottom of this page.
LF Payne served as Wintergreen's Development Manager from 1973 - 1976 and the President of Wintergreen Development, Inc. from 1976 to 1988. Prior to his Wintergreen service, LF graduated from Amherst County High School, the Virginia Military Institute (BS Civil Engineering), The Darden School of Business at UVA (MBA), and served in the US Army as a Company Commander in South Korea. After his Wintergreen service, LF served as a Member of the United States Congress for five terms representing Virginia's 5th Congressional District (including Wintergreen). Payne was a founder of McGuireWoods Consulting, a subsidiary of the McGuireWoods law firm, and served as the President and CEO of MW Consulting from 1998 to 2020. He is currently the President of Three Ridges Group LLC, a member of the Board of Visitors of the University of Virginia, and a member of the Executive Committee of the US Association of Former Members of Congress. LF and his wife Susan live in Charlottesville and have four children and nine grandchildren.
Tim Hess passed away on November 26, 2025. He was 76. Read his obituary here. A celebration of life is set for Saturday, April 25, 2026.
Tim Hess arrived from the Sea Pines Company at Hilton Head Island in November of 1975 as part of the opening resort team to hire and train the initial hospitality staff. Over the next six years as Food and Beverage Director, Tim was responsible for the operation and opening of multiple restaurants, conference facilities, and bars. Only intending to stay at Wintergreen for a year or two, but he met Lynne, his lovely wife of 47 years, and they became one of the first permanent Wintergreen families to build a home and settle in the Rodes Farm area of Stoney Creek. In 1981, Tim joined Wintergreen Real Estate Company and helped build the vision set out by the master plan of the founders. In 1999, an unfavorable decision in a lawsuit caused Wintergreen development and the real estate company to hand the keys back to the bank. Tim was instrumental in putting together a group of his partners: Dick Carroll, Peter Farley, and Kyle Lynn; with the assistance of their angel investor, Michael Donovan, they were able to form High Country Associates, LLC. This entity then purchased all the remaining development assets, the real estate company, the utility company from the bank, and continues to work hard to fulfill the remaining vision of the community master plan. In recent years, the real estate company has been sold to The Pacific Group, and the utility company to Aqua Virginia.
Jay Gamble, General Manager of Wintergreen Resort for four years, brings 44 years of ski industry experience, including management roles at top resorts like Killington, VT, and Sunday River, ME. A Clemson University graduate and South Carolina native, Jay’s passion for the mountains began with family trips to western North Carolina. He has been a ski resort GM for 27 years and served on the Ski NH Board for 23 years, chairing its Legislative Affairs Committee for 20 years. Now settled in their newly built Stoney Creek home, Jay and his wife Michelle look forward to making Wintergreen their permanent home after retirement.