Welcome to Route 20: America’s longest road stretches from Boston to Oregon (2024)

Some of Boston’s most significant landmarks flash their lights around Kenmore Square. There’s the conspicuous double-walled Citgo sign, its thousands of LEDs gleaming across a 60-by-60-foot surface. About 1,200 feet away, the Red Sox ply their trade under massive light stanchions. Nearby bars serving Sam Adams and vendors hawking hot dogs make America’s oldest ballpark and its noisy corridors impossible to miss.

But a smaller landmark often gets overlooked by herds of tourists and even many locals milling through one of Boston's busiest intersections. To some, it appears to be just another traffic sign, but to others, it's a historical marker — or perhaps a dare to pick up and hit the open road.

It’s a green sign that tells onlookers that, from where they stand, it’s 3,365 miles from Boston to Newport, Oregon.

The sign marks one end of Route 20, the longest contiguous road cutting across America, which essentially runs from coast to coast. From Oregon, the highway passes through Idaho, Montana, Wyoming, Nebraska, Iowa, Illinois, Indiana, Iowa, Ohio, Pennsylvania and New York before ending in Massachusetts.

Former MassDOT Highway Administrator Thomas Tinlin was part of the team that installed the road sign on Commonwealth Avenue back in December 2016. Elected officials in Oregon had reached out to ask if Boston would like to put up a traffic sign to match one just like it on the other coast.

After a contentious presidential election season, Tinlin loved the idea that a Massachusetts highway marker and its twin in Newport, Oregon, could serve as a reminder that “no matter where you live, you’re part of one country.”

“There were a lot of things that were dividing the country, and here we are with this cool road, that joined us all together,” Tinlin said. “... If I get on Route 20 in Kenmore Square, my next stop, if I wanted it to be, could be Newport, Oregon.”

Oregon state Rep. David Gomberg said he pushed for the marker in Newport after seeing a similar one in his hometown of Sacramento that establishes the last stop on Route 50 west, more than 3,000 miles away from its other end in Ocean City, Maryland.

“The three most photographed spots in Newport, Oregon, are the lighthouse, the bridge across Yaquina Bay and a sign that says this is the way to Boston,” Gomberg said.

Once Newport installed its own Route 20 sign, Mayor Dean Sawyer, who was a city councilor at the time, asked Tinlin if Boston wanted to put one up, too. The former highway administrator said he jumped at the opportunity.

“It’s easy to forget that what we do matters,” Tinlin said. “And what we do — whether it's roads or tunnels or bridges or mass transit or planes — whatever it is, it's really all about keeping people connected to one another.

“When you realize that I can take this road and travel through multiple states and see multiple things, in a way I just feel like the country gets smaller," he added. "And we start to realize that our little piece of the world is just a piece of a much, much larger puzzle.”

On a recent afternoon, lifelong Massachusetts resident Brittany Erazo was walking through Kenmore Square and noticed the Route 20 sign for the first time. She pulled out her phone and snapped a picture of it.

“I didn’t know about this,” she said. “You learn something new every day.”

Boston University sophom*ore Ivan Solzhenitsyn had also never taken note of the sign before.

“Oh my god — seriously? I didn’t know,” Solzhenitsyn said. “So Route 20 starts here and goes all the way to Newport? Wow, that’s an interesting fact. I’m really glad that I learned about it.”

Solzhenitsyn has never driven on Route 20, but he has taken other routes to cross America, taking off in Vermont and reaching San Francisco. He said he likes road trips, seeing new sights and making memories with pals.

“It’s bonding with a friend, and seeing the beautiful country,” he said.

Nancy Steinberg lives in Newport, Oregon, but grew up in Waltham. She said she lived in the Beaver State for years before realizing the Route 20 in her West Coast home was the same stretch of road she grew up driving in her hometown.

“I have always, for 20 years, seen it as a thread that connects me to my roots and to my parents who are still there [in Massachusetts],” Steinberg said. “For me personally, it bridges this great country where I grew up and lived on one side of it and now live on the other. And it makes it seem just a tiny bit smaller when I'm missing home.”

It’s this drive to connect communities that inspired Bryan Farr to start the Historic U.S. Route 20 Association in 2012, two years after his first road trip along the highway. Farr said many people know about the hugely popular Route 66; why not the lesser known Route 20?

“Route 66 and Route 20 were created on the same exact day,” Farr said. “So when you look at it that way, they're the same age, and the same things can be seen … that's what we're trying to do, is just draw the attention that there are other roads out there that are just as significant as Route 66.”

Part of the mission of Farr’s association, which has about 400 members across the U.S., is to get communities along the route to somehow mark the roadway.

Farr said several residents and community groups have put up unofficial signs for the road in their own towns and cities. Signs are located in Massachusetts municipalities like Marlborough, Sudbury, Northborough and Chester — a tiny town in Hampden County where Farr lived for years.

New Yorker Michael Czarnecki honors Route 20 with poetry. He first drove the entire length of the route in 1996. Since then, he’s repeatedly written about his adventures on the highway. He now drives Route 20 to read his poems about Route 20. He remembered one conversation he had in Iowa during one of those trips.

There "was a woman, she was probably 40 years old or so,” Czarnecki said. “She goes, ‘Your reading really inspired me to start traveling and exploring Route 20.’ And then she said, ‘On a motorcycle — and this time not on the back.’ Which I thought was so cool.”

Tinlin, the former highway administrator, said he hasn’t driven all of Route 20. But he might consider it for a future family trip.

“Maybe that's the next trip? … Maybe we do the Griswolds, we load up, and it'll be like Chevy Chase, ‘[National Lampoon’s] Vacation’ and just go hit it,” he said. “I'll put on my ’80s music track and hit the road. Drive my kids crazy.”

If Tinlin does hit the road, maybe it will be to mark a birthday. Route 20 will turn 100 years old in 2026.

This segment aired on September 22, 2023.