The Longest Highway In America
Parts of U.S. Route 20 existed long before automobiles were invented. Sections of the corridor followed ancient Native American trails that were later transformed into stagecoach and turnpike lines.
Today, Route 20 is still the longest highway in the country, spanning 12 states from Boston to Newport, Oregon, and covering 3,365 miles in the process.
The Metric of Length
Giving a highway a superlative title means the metric must be defined upfront. When saying Route 20 is the longest highway in America, it means the length is measured by total signed route mileage. The metric does not include ferry gaps and overlapping road sections.
If the definition becomes less strict, other United Sates routes would emerge as title earners. For instance, one could measure the longest continuous interstate highway instead or look only at historic roads built before 1964.
The Quest To Build America's Longest Highway

U.S. Route 20 is the result of a grand plan to link Boston to the Pacific Northwest. The highway was established in 1926 when it became part of the U.S. Highway System.
Before the route existed, however, drivers who tried to travel across the country were frustrated by strangely named trails and symbols on telephone poles. They also could not rely on local county maps to get them where they needed to be.
To bring order to the chaos, the Secretary of Agriculture created the Joint Board on Interstate Highways in 1925. This was done in collaboration with the Bureau of Public Roads. The goal was to set up a standardized federal highway system with simple rules.

One of the rules was that transcontinental routes or main east-west routes would be designated even numbers ending in zero.
As such, U.S. Route 20 was created and authorized, according to the U.S. Highway System. Route planners designed the highway to run in a straight line and connect the industrial ports of New England through the Midwest.
They did not intend to build a new road from scratch. Instead, they used stone turnpikes and local roads to create one long highway, but while the system debuted in 1926, the route was still not complete. There was yet to be approval for an extension across the Northern Rockies and Pacific Northwest.

In the absence of that approval, the western terminus of Route 20 stopped at the eastern entrance of Yellowstone National Park.
United States numbered highways are not designated in Yellowstone or any other National Park, so Route 20 does not run through it (technically speaking). The route 'restarts' at the western entrance of the park, and was extended in 1940 to stretch through Idaho and end at a junction with Route 101 in Newport, Oregon.
For some, this means the highway cannot be the longest highway in the country, despite the U.S. Department of Transportation confirming that it is.
Driving Through Twelve States On One Highway

As mentioned, Route 20 passes through twelve states: Massachusetts, New York, Pennsylvania, Ohio, Indiana, Illinois, Iowa, Nebraska, Wyoming, Montana, Idaho, and Oregon.
Part of the highway follows the old Boston Post Road in Massachusetts. This road was used for transporting mail between Boston and New York as far back as the 17th century.
Route 20 also offers the chance to see some spectacular natural wonders along the way, including Lake Erie, the Finger Lakes, the Indiana Dunes National Park, and the Craters of the Moon National Monument. The highway also crosses the Cascades and comes to an end less than one mile from the Pacific Ocean.
How Long Does It Take To Drive U.S. Route 20?

Those who want to drive the entire length of Route 20 should plan for at least two to three weeks on the road. Whether you drive from New England to the Pacific Northwest or vice versa, there is a lot to see and experience as alluded to above.
Many people kick off their journey in Newport, with the western terminus starting near the U.S. Route 101 intersection. From here, the route passes through the Cascades and the Oregon Badlands.

When the highway reaches Idaho, it passes downtown Boise before getting to the Craters of the Moon National Monument and Preserve. Next up is ten miles of the Montana landscape before moving on to Yellowstone.
The road is unnumbered in Yellowstone and becomes Route 20 again at the other end. Nebraska is up next and then Iowa. After passing the Mississippi River, the road heads to Indiana and Ohio. Then it runs along Lake Erie as it passes through Pennsylvania. The Finger Lakes are the next major stop en route to Albany before reaching the eastern terminus in Boston.
Some Of America's Other Longest Highways

America boasts several other long highways too. U.S. Route 6 is actually considered by many to deserve the title of longest highway (because of Route 20's unnumbered section in Yellowstone). Route 6 is 3,205 miles long as it stretches between Provincetown, Massachusetts, and Bishop, California.
Even though it does not officially earn the title of longest highway, it does have the designation of the Grand Army of the Republic Highway. It was even longer before the western end was truncated in 1964, a move that ultimately handed the 'longest highway' title to Route 20.

Route 30 is around 3,112 miles (5,008 kilometers) long and connects Atlantic City, New Jersey, to Astoria, Oregon. A large section of this highway was once part of the historic Lincoln Highway, America's first transcontinental motor road.
Route 30 is also the third-longest U.S. Highway in America after Route 20 and Route 6. Interstate 90 is 3,020 miles (4,860 kilometers) in length and links Seattle, Washington, to Boston, Massachusetts. It is the longest interstate highway in the country and was authorized in 1956.
America's Endless Road
Driving Route 20 can certainly feel like you are on an endless highway, but there is so much to see that time flies by. After all, it is not every day that you can experience natural wonders throughout twelve states and stop in countless small towns all in one road trip.
Route 20 is one of the best ways to experience both new and old America all in one go.