The Winn Homestead began in 1875 when Jesse Z. Winn homesteaded in Umatilla County on the current spot where the 3rd and 4th generations now live. There Jesse farmed with horses, and in 1916 his son, George W. Winn, decided to build the barn that you see in the pictures. It was built in May of that year by 30 men, taking 30 days and $3000 to complete. The bottom half of the barn is divided into a dairy cow side with concrete floor and a horse side with dirt floor. By 1936 the Winn's began farming with tractors and the horses were sold. During the late 20s or early 30s the dairy cows were sold, leaving just beef cattle and crops to be raised. From the 40s to the 80s, George Robert Winn farmed the homestead, raising a variety of crops including potatoes, beans, wheat, barley, dry peas, green peas, spinach seed, lettuce seed, wheat seed and strawberries.

Strawberry production began in the early 1950s with both u-pick and fresh market berries sold on the farm. Over the next half century the family enjoyed teaching over 10,000 youth how to work productively on the farm, picking, sorting, hoeing, irrigating, and selling strawberries. Our customers were always glad to see and purchase our quality fresh berries, and we were happy to see many of them return, year after year. The strawberry tradition continued for over 50 years until deer invaded the area and destroyed more than 50 percent of the crop for 4 years in a row. This event caused Preston and Arlene Winn, 4th generation farmers, to discontinue berry production.

The barn, a centerpiece of the farm, seemed to be a vastly underutilized asset. The barn was and is photographed regularly. Preston and Arlene Winn decided to begin a new venture on the farm with a focus on the barn, and thus launched Winn Homestead Events.

While crops continue to be grown on the farm, it is leased out to others to tend to the daily routine of care for the land. Preston and Arlene have focused their attention on teaching school and now, hosting events in our beautifully landscaped barnyard area.

Our daughter, Kendra - a 5th generation Winn Homesteader, has developed this web site.