Sisemore Bridge was located on the Deschutes River at the site of Farewell Bend, near the present Old Mill District in Bend. It was built by John Sisemore in December 1904. He was born in Kentucky on Dec. 14, 1835. Sisemore came west to Utah in 1853 and then on to Northern California, where he prospected for gold. He managed to make some money from his placer mine but also spent most of it. The prospector's health began to deteriorate, so he left the mines in 1857 with a reported $32,000 in gold dust. He moved to the Willamette Valley in Oregon and bought some cattle, which he drove south to the mines and sold for a huge profit. Sisemore decided to go into the livestock business. He ranged his cattle in several locations in Eastern Oregon but made his general headquarters in Jackson County. A severe winter resulted in much of his cattle herd being decimated.
In 1886 Sisemore bought the ranch of John Y. Todd at Farewell Bend and also patented a homestead claim along the Deschutes River. He had married Mary Pelton, but they ultimately divorced. He later married Susan Brewster on Nov. 27, 1908. She was in ill health and soon died. John built a wooden bridge across the Deschutes River at his ranch site. The bridge was 385 feet long and cost him $385. He completed planking the bridge just before Christmas in 1904. The Prineville Review reported on the bridge on December 2, 1909:
County Judge Ellis phoned over from Bend Sunday morning to sheriff Elkins that every bridge spanning the Deschutes River between Lava Butte and Laidlaw had gone out from the effects of the flood and the accompanying busting of log booms. The Ryan Bridge, Dutch John Bridge, Sisemore Bridge, Drake Bridge, Riley Bridge and Laidlaw Bridge are affected, the last named being the only one left upon which travel may yet be accommodated, though even that is in a precarious condition. Of the six the Sisemore and Laidlaw are county structures. Below Laidlaw Bridge the bridges are intact. A report late last week had the Cline Falls Bridge going over the falls, but the stage driver crossed it Monday morning and said it was standing there as it always had. Lower Bridge and Tetherow Bridge likewise are not in any stress. The water rose from two to three feet according to the rivers width and sticks of timber breaking loose from booms were responsible for practically all of the damage done. Deschutes bridges are built low as no floods are ever expected in the river, eight inches being the usual freshet rise; and thus, they fell easy victim to the flow. The Drake dam at Bend was also a sufferer. This was in partially finished condition, and the flood swept it out of existence, demolishing all the work done. It will require many a dollar to repair the damage. Not in the time of the oldest inhabitant has the Deschutes been known to go on a rampage before, that is above the mouth of the Crooked River and below the lava flows. Here-to-fore the flow has been practically the same throughout the year between those two places and the freshet of spring was marked solely by the amount of coarse sand seemingly held in suspension in the water. A rise of seven or eight inches hardly noticeable, is about the usual, while once in ten or twelve years would rise as high as twelve inches and once in history was it eighteen inches at the Staats place above Bend. The Sisemore Bridge, which was many years ago presented to the County [Crook] by John Sisemore with the condition that the county keep up repairs, will undoubtedly be replaced by the county in the near future, when it is, it will probably be a steel structure, as more lasting. It cost Sisemore $1.00 a foot. He served as road master for Crook County in this area.
Sisemore sold his ranch in 1905 for $6,500 and then bought property in the newly developing town of Bend. His health began to fail in his later years. He died in Grants Pass, Oregon on Dec. 16, 1910.
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