Pull out of the parking lot at Nye Beach in Newport, Oregon. Hang a left on Olive Street, with the Pacific Ocean behind you. Drive a few blocks, stop at the traffic light, and then merge onto Route 20.
In just over 65 hours, you’ll arrive under the Citgo sign in Kenmore Square.
Between Oregon and Boston, Route 20 winds through twelve states and stretches across 3,365 miles, making this unassuming road the longest highway in the United States.
The road predates the nation’s interstate highway system by decades, and it is less well known than romanticized, singsong companions like Route 66, but it still connects the two coasts and weaves together an expansive piece of America.
“Most people just think 20 goes to Worcester, and that’s it,” said Bryan Farr, president of the Historic Route 20 Association.
“You’re following one continuous roadway across the country.”
The number is often discarded in favor of older names like Commonwealth Avenue in Allston, or Main Street in Watertown, or Boston Post Road in parts of the MetroWest.
Yet for history buffs who don’t mind stoplights, the route could be a Bostonian’s best road trip prospect.
Springing west from Kenmore Square, Route 20 weaves past the rolling hills and hippie B&Bs of Western Massachusetts, the shuttered factories of the Rust Belt, the tract houses of the Chicagoland suburbs, and the plains of the Upper Midwest.
It eventually curves through Yellowstone National Park and Oregon’s tall forests before settling in the city of Newport, a few feet from the Pacific coast.
This trip is not for the faint of heart.
Route 20 follows unseparated local roads rather than interstate highways for most of its length, so it is tough to imagine a less efficient way to traverse the country.
But the full route takes travelers through small towns, national parks and historic landmarks along the way.
“It’s definitely a worthy trip. You get an experience from the highway,” said Farr, a Western Mass resident who has traversed Route 20 twice. “You’re seeing the history of the country, just on one road.”
Route 20 has carried parts of American history on its own. In Massachusetts, the route traces its origins to a Native American path that was first created before colonists arrived.
That pathway later became a key colonialera connector between New York and New England, and both General Henry Knox and George Washington used the route to travel to and from Boston during the Revolutionary War.
By the 1920s, Massachusetts had upgraded this east-west path into a full-blown highway, and as the automobile gained popularity, the federal government eyed a national highway network.
Federal officials cobbled together existing roads from Massachusetts to the Pacific and in 1925, named this collection of roadways Route 20. Bostonians now had a direct route across the country.
Eventually, postwar freeways like I-90 emerged as more efficient long-distance roads, and Route 20 lost its luster. But Farr views the route’s stop signs and low speed limits as a feature, not a bug. He hopes more road trippers will use Route 20 to see a vast slice of America barely visible from interstates. “When you’re forced to slow down a little bit and take your time on a highway, it broadens your perspective,” he said. “It’s connecting communities across the country.”
