Within three years, he owned the land, equipment, and stock free and clear. In 1883, however, his wife became ill, and Benson sold his holdings for six-thousand dollars and moved to Colfax, Washington, seeking a dryer climate. Despite the move, his wife's health continued to deteriorate, and in 1890, she passed away, leaving Benson a widower with three children, Amos, Alice and Caroline. Upon Esther Benson's death, Benson decided to return to St. Helens, Oregon, where he re-entered the timber business.
Simon Benson soon entered into a partnership with Ordway and Weidler, to whom he had been selling logs. The partners purchased a large tract of timber, and built a logging railroad to transport logs from the woods. When the price of logs declined, both of Benson's decided to leave the business and sold their interests to Benson. Benson, always an innovator, experimented with using a donkey engine to yard logs, which practice he soon perfected.
Benson maintained several rough shanties near the falls [Beaver Falls] as headquarters for his crew. The group depended upon two sources of power to harvest the big trees: oxen and the water of Beaver Falls and Beaver Creek. Sometimes that power would fail, and he was finally forced to abandon his first camp because the volume of water was not great enough to carry the felled timber to the mills at Beaver Slough in Inglis.
"His experience while traveling Beaver Creek Road sowed the seeds for his later deep interest in improving Oregon's roads," wrote his daughter, Alice Benson Allen. "During the rainy seasons, travel was often a triumph over mud; wagons needed strong wheels. There was also the constant threat of being thrown from the wagon while going down the rough canyon past Beaver Falls."
As a businessman, Benson was always willing to try new things. For instance, he was the first to abandon oxen teams for locomotives, which reduced his costs by more than half. This gave him the capitol to outbid other operators for homesteaders' timbered property. "It wasn't long," said Benson, "before any homesteader who wanted to sell out would come to me. I always bought."
In addition, specially-constructed, cigar-shaped rafts holding as much as 5 million feet of logs each allowed Benson to cut his shipping costs by as much as $150,000 a year. In 1910, he sold his timber holdings and relocated to Portland, constructing the Benson Hotel and becoming involved in philanthropic work. Among his many projects was the Columbia River Highway.
Even though Benson's initial gift of $10,000 to construct a usable road around the base of notoriously unstable Shellrock Mountain in the Columbia River Gorge was a failure, it still stimulated interest in highway construction.
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Benson later financed a mile of the highway in Hood River County near the Multnomah County line. In 1914, when Hood River County balked at the cost of construction in their vicinity, Benson underwrote a $75,000 county bond measure and pledged to pay any amount in excess of the construction costs.
According to "Oregon Routes of Exploration," published by the Historic Preservation League of Oregon, Samuel Lancaster, while hiking the trail to reach the falls with Simon Benson, remarked, "Wouldn't it be nice if there was a footbridge across the lower waterfall, with a path up to it?" To which Benson replied, "How much would it cost?" Lancaster calculated the cost on the spot, and Benson immediately wrote a check, saying, "Then go ahead and build it."
Erected in in 1914, the Benson Footbridge, named for its benefactor, replaced an earlier log bridge over the chasm.
When work ground to a halt on the lower highway in Beaver Valley, Benson argued passionately for funding, but when it was not forthcoming, he donated $21,000 of his own money to get the ball rolling.
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As late as 1917, the Beaver Creek Bridges had not been completed (the last would not be finished until 1920). Temporary timber spans served to carry road workers back and forth. While traveling over the route with Herbert Nunn, Simeon Benson was greatly disturbed by the difficult Inglis detour.
"The first effort of the commission in finishing the highway," Benson said in 1917, "will be in putting in the bridges across Beaver Creek so that the grade between Delena and Inglis can be used."
Benson backed up his words by donating $21,000 of his own money to get the ball rolling. The impetus was just what the state needed, and an additional $50,000 was quickly budgeted toward macadamizing the Clatskanie-Delena section.
Benson's interest in the Beaver Valley was personal. He had been one of the first to enter it in search of a living. Working for lumberman John Beavis on Tide Creek allowed him to save enough within a year to make a down payment on 160 acres, secure credit, and move his family to Columbia County [in 1880, forming the Benson Timber Company]. In 1888, desperate for money to cover debts related to nursing his sick wife, he turned to the area of meandering Beaver Creek.
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...his initial camp and lumber mill were atop Beaver Falls.
Benson was appointed chairman of the State Highway Commission in 1917.
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He also constructed also constructed the famous Columbia Gorge Hotel in 1921 and personally took rake in hand to help spread the "hot stuff" mixture during the paving of the highway at Rowena [a ceremonial gesture during the dedication festivities there marking the completion of the paving of the highway].