The Oregon Trail
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Because of the dangerous rapids along the central Oregon portion of the Columbia River, and the rugged basalt flows along the Columbia's shores, the Oregon Trail dropped about 17 miles south of the Columbia, following a sandy route through bunchgrass and sagebrush.  The Oregon Trail entered Sherman County at the McDonald crossing of the John Day River, about 10 miles east of Wasco.

A fork in the Oregon Trail occurred just after exiting the canyon of the John Day River.  Most emigrants took a right (west) fork of the Trail to go to The Dalles, but a few took a left (southwest) fork that led the down Grass Valley Canyon to the Deschutes River crossing at the present-day Sherar's Bridge (a sufficient wooden bridge was built in the 1860's), and on to the Barlow Road.

Those traveling the Oregon Trail toward The Dalles headed toward Emigrant Spings for the first watering after the  McDonald crossing.  The Trail traversed Emigrant Canyon, Biglow Canyon, Scott Canyon, China Hollow (about 2 miles north of Wasco), Spanish Hollow (present-day Hwy 97), and then turned north, traveling down Mud Hollow to the Columbia River just west of Biggs.  From there, the Trail followed the Columbia to the Deschutes River crossing (now under the backwaters of The Dalles Dam), where the Trail leaves Sherman County.  The Deschutes crossing was very dangerous...there were many large rocks and a very rapid current.  By by 1864, a toll bridge had been established.