A classic road trip on America's longest highway


An aura of history and romance surrounds famous highways like Route 66. Modernization, as well as the pursuit of convenience and safety, have led to more four- or eight-lane highways crisscrossing the nation, like I-90, I-35 or I-94. Finite stretches of state and county roads may still have that timeless two-lanes-cutting-through-the-countryside appeal, but road trips that follow the cross-country highways of yesteryear mostly take place in people’s imagination, not on the blacktop

However, there is one historic highway where it is still possible to get in touch with the glory days of the American road trip. U.S. Route 20 covers 3,365 miles from Boston, Massachusetts, to Newport, Oregon. It is currently the longest highway in the country. For most of its length, Route 20 runs roughly parallel to I-90, which connects Boston and Seattle (a distance of 3,100 miles).

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