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Originally Posted by HungLikeJesus
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Unfortunately, Oregon does not seem to have made it into your linked article.
But in terms of absolute safety and necessity, and in reference to UG's OP about "Libertarian" values,
the Barlow Trail is prized because it was so important to the settling of the Oregon Territory.
It ran from The Dalles around the south side of Mt Hood to Oregon City
The Barlow Road, built by Sam Barlow in 1846 with governmental approval, was entirely paid for by private money ($4,000), labor, and enterprise.
Tolls were about $5 / wagon and often paid with cattle, chickens, etc.
Barlow was licensed to collect tolls for only 2 years.
On a completely personal note, our family drives this same route frequently on picnics and fishing trips to the nearby rivers.
Even today it is almost impossible for us to believe they were able to find their way thru these forests and to build a wagon trail using the tools of their day.
WIKIPEDIA ARTICLE
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Before the opening of the Barlow Road, pioneers traveling by land from the east followed the Oregon Trail to Wascopam Mission (now The Dalles) and floated down the Columbia River to Fort Vancouver, then a perilous and expensive journey. It was also possible to drive livestock over Lolo Pass on the north side of Mount Hood, but that trail was too rugged for vehicles and so unsuitable for wagons.
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