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Just after World War II, Dorothy and Jack Evans built a small cinder block building overlooking Cayuga Lake, and used it to sell their farm produce, homemade ice cream, and dairy products. The business quickly grew, and they soon added a small lunch menu. The stand was sold to Harry and Frances Dearstyne in 1951, and they enlarged the building in order to serve legal beverages. In 1962, Elmer and Lou Morgan bought the Glenwood and added a full restaurant, offering a special Friday night fish fry. In 1974, Lee Denman and Dave Pepin took over, brought in live bands on weekends, and invented the now world-famous Pinesburger.

In 1979, the Glenwood was purchased by the Hohwald family: dad Gil, sons Bill and Ken, and daughter Debbie Herrmann. Gil, Bill, and Debbie have since retired and left the business. The restaurant remains a family business, and is now run by Ken and his nephew Corey. Ken and Corey, along with their staff, continue to attract a strong following of casual diners who enjoy a homey atmosphere and good food, and continue to offer their famous fish fry and Pinesburgers every day.