The J. H. Stepp family moved to the farm off Pace Road in January, 1967, and J. H. (the family patriarch) gave it the name "Hillcrest Orchard." The farm had been the home place of a distant cousin, Polk Hill, who was known to let visitors to the farm glean and pick up apples at the end of the season. Mama Mann, J.H.'s mother-in-law, continued the business and each year the number of people who showed up to pick their own apples grew.

J.H.'s family had previously operated the J.H. Stepp and Sons Packing House, General Store, and Hardware Store in Dana. By 1972 J.H. was ready for a change, maybe a slower pace, and on trying "pick your own apples." The first year J.H.'s wife, Yvonne, and Mama Mann worked out of a car until an8' x 8' stand was built. By 1975 the current "apple house" was completed. The two sons, Joby and Mike, were working full time in the orchard and also taking care of 200 rented acres. Many apples were still taken to the packing house but the pick your own trade was growing. During the selling season the eldest daughter, Sonya, the two daughters-in-law, and J.H. and Yvonne worked the pick your own trade.

Many apple growers in Henderson County depended on the juice and processing market to sell their apples. But, in the 1990s those markets began to disappear as plants closed or moved out of state due to the importing of foreign apple juice concentrate. Fortunately, Hillcrest Orchard had little dependence on these markets. J.H. stated, "The hardest thing was waiting on people to come and pick, knowing you have nearly fifty acres in apples just hanging there."

As time went by, the farm staff changed. The eldest son, Joby, married and moved to Virginia to farm and Mike, the youngest son took a job off the farm due to several years of low production from frost and freeze. With little or no fruit, the farm could not support all of the families. As time went by, Sonya continued to help at the farm. The business grew with a continued increase in people wanting to pick their own apples. Mike returned to the farm in 2003 and soon other changes were incorporated into the family business. School tours which began in September that year experienced much success and wagon rides were offered on weekends.