Jess M. Gray served first as a stage driver for Hugh Jackson, and soon thereafter saved enough money to buy his own stage, freight wagon & team so he could subcontract the services from Jackson. Jess started out as a stage driver at age 16, first taking the run from The Dalles to Shaniko. After acquiring his own stage and team to pull it, he took over the run between The Dalles and Canyon City in the fall and winter, operating his own freight line from Shaniko to central Oregon in summer. Toward the end of the stagecoach era, Gray's fall and winter run (Jackson's contract) took him from the Umatilla house down through 8-mile, Boyd, Nansene, Chicken Springs, Keen, Shearar's Bridge, Flanagan, Bakeoven and finally to Shaniko. From Shaniko, G.M. Cornett took the run to Antelope, Burnt Ranch, Ashwood, and finally to Mitchell. Another contractor took it from there to Canyon City.

The Dalles to Shaniko stagecoach run was 58 miles. In good weather, that run could be made by one driver with a single team of hard-working horses. It was a long, dusty trail in summer. In fall and winter, the trail alternated between muddy and slick with snow or ice, but it was always cold. Jess Gray related to family members how he had to bundle up in sheep skin clothing, and even at that the chill would settle into his bones, permeating his entire body and numbing his limbs. That was simply a way of life for Jess (and many others whose work took them outdoors) back then.

Because of the cold weather and often nasty conditions under which they drove, Jess and the other veteran stage drivers learned many tricks that enabled them to minimize their exposure to the elements. One of these was the way they picked up and delivered the smaller freight parcels that were transferred at individual ranches.

In the final years of the winter runs, pouches were tied to the gates of each ranch, for transfer of documents or freight. The pouches resembled socks (and probably were substituted by socks from time to time) and were therefore referred to as "socks." 

Gray said, "At times our passenger list contained some pretty hard looking men, but I was never held up or molested. On the freighting runs to Prineville, Burns, Silver Lake, Bend or Lakeview, I generally hauled merchandise, farm supplies, machinery, lumber, nails, liquor and clothing. No runs were made for any particular outfit or business concern. On the return trips we brought back wool, hides, wheat, meat and other farm products. 

"It was hard work, always away from home, exposed to all types of weather, muddy and boggy roads, snow, ice or dust, breakdowns, sick horses, broken harnesses, wagons or equipment; wagons sliding off the road; dry camps without water, sleeping out under the start; poor food or none at all; run-away teams which would break up the wagons and scatter the merchandise. It was a hard life even when conditions were at their best. Most of the drivers were hard drinkers of bad liquor and lived short lives." Jess was the last of the pioneer stage coach and freight wagon drivers alive in this area by the 1940s.

Though he was "never held up or molested" on his stage or freight runs, Jess did encounter some of the worst of the worst "bad" men of his time, shortly after the stage runs ceased entirely in 1914. That story can be found under the title, "Life with Pancho Villa," which will be posted to this section of the site soon.