At the age of 65, when most people are thinking about retirement, Charleston, WV, native Margaret Drennen convinced her beloved husband, Judge William M. Drennen, to purchase 10 acres of land in Shepherdstown. Upon purchase, she marveled at the sheer beauty of the land and wondered if she should purchase the “whole darn thing.” She again contacted her good friend Henry Shepherd and bought the remaining 250 acres. “Maggie” admits at first she didn’t know what to do with the land. With the assistance of her son-in-law, Hank Walter, they began to explore opportunities for their newly acquired property. A market consultant was hired and their assessment was the land was good for either of two recreational amenities, in conjunction with an elegant custom home community. Either dam up Cress Creek, which was called Swearingen’s Run in those days, flood the hundred-year flood plain, and sell property around the lake, or build a golf course. Maggie remembers reading the proposal and commenting, “My husband and I play golf, we don’t like boats.” So she built a nine-hole golf course that opened in 1988.

The club’s name was derived from the watercress that grow in the stream that passes through the golf course. The original nine hole routing are today’s 10, 11, 18, 1, 2, 6, 7, 8 & 9. In 1991 an additional nine holes were added. We can all be thankful that Judge Drennen and Maggie didn’t like boats!

In 2014 The Club was sold to three of its members: Dr. Troy Foster, Fred Parsons and Eric Lewis. The Club at Cress Creek has a storied past and a very bright future.