The April 15 Chieftain ran a photo of the Pie and Coffee Shop in the Out of the Past column, and asked for more information from anyone knowing more about this place. Carolyn Maasdam, of Enterprise, responded with the following information:
All about the Pie and Coffee Shop
The Pie and Coffee shop was built and opened in the early 1950s by Ned Boyce on the site where the Wilderness Inn is today in Enterprise. They served hot, freshly baked pie and coffee. It was a place where the cops hung out for pie and coffee.
They expanded it to a summer drive-in. You’d find as many as eight cars lined up waiting for service. They had car hops who would come out and take your order and then bring it back on a tray that you could set on your window.
In 1955 and 1956, they added an addition and put in the first soft ice cream machine in Wallowa County. The machine was 5 feet tall, 6 feet long and 4 feet wide and took up most of the room in the addition. You poured a mix called Mello-Freze into the machine and out would come ice cream. On the first warm days of the year it was hard to keep up with demand. There would be a line that snaked around the corner.
I worked there in the summer of 1960, and the ice cream machine and room was all mine. We made sundaes, parfaits and banana splits, too. They had little tables by then so you could eat there.
Hamburgers were 35 cents. To be a car hop you had to be 18, and I was only 17, so most of that summer I made ice-cream and washed dishes. But it was lots of fun.