Everyone knows the song. It’s been covered by artists ranging from Bing Crosby to Chuck Berry to the Rolling Stones to Depeche Mode to John Mayer.

“Would you get hip to this kindly tip. And take that California trip. Get your kicks on Route 66.”

Soon we may need a new song for an even longer historic highway. Is there anything that rhymes with Route 20? Budding songwriters get to work now, because if one Massachusetts man has his way, Route 20, which begins in Boston and stretches to Oregon, will become just as renowned as the iconic 66.


In July, the Massachusetts House of Representatives approved a bill designating US Route 20 as a historic highway. The bill is currently under review in the Senate. The designation would allow Massachusetts cities, towns, and, most importantly, businesses, to promote the road as a landmark. Get ready for an onslaught of Historic Route 20 T-shirts.

The idea to turn Route 20 into a historic highway came to Chester resident Bryan Farr when he was looking for an alternative route for his artistic eye and adventurous spirit. Farr, 42, a meteorologist-turned-bartender who loves both photography and road trips, wanted to author a road trip coffee table book. However he wasn’t interested in digging around for material along the oversaturated 66, which has already been immortalized in literature, music, TV, film, and enough refrigerator magnets to fill the Grand Canyon. He needed a new artery to tap into.

“I would see all of these exits for Route 20 off the Mass Pike, and then I would think ‘Where does 20 go?’ I looked it up, and it goes all the way across the country. That’s kind of awesome,” he said.

The view along the Keystone Arches Trail in Chester.
The view along the Keystone Arches Trail in Chester.Christopher Muther/Globe staff

In fact, at 3,365 miles, it’s the longest road in the United States. It begins in Kenmore Square and ends within a mile of the Pacific, in Newport, Ore. By way of comparison, Route 66 is just 2,448 miles and travels from Chicago to California. For exact Route 66 directions, please refer to the lyics of the song.


In Route 20, Farr had found his epic road trip, but he also found a cause.

“My Route 20 road trip in 2010 was supposed to be a once-in-a-lifetime thing,” he said. “Go one time and take pictures. I wanted to write the book and move on from that. Then maybe do other roads, or some other photography project, but just get my name out there a little bit.”

Farr spent two weeks on Route 20, taking 1,800 pictures across 12 states. He showed an early prototype of the book to friends, who told him they wanted to know more about the towns in the photos. So Farr began sending e-mails and collecting information about mom-and-pop shops, quirky museums, old monuments, and small towns along the highway. A friend told him he should use all of his newfound knowledge and start an organization to help promote the highway, its uncelebrated past, and its small towns.

“I thought ‘Why not look into it?’ And a few months later we were officially a nonprofit organization,” he said. “The Historic Route 20 Association is now a public charity with a mission to promote travel and tourism.”


Farr’s official title is now president of the Historic US Route 20 Association. It’s become his full-time job and the state recently awarded the organization $75,000 to open a Historic Route 20-Gateway Hill Towns visitor center. He said the group will soon be applying for a historic highway designation in Iowa and has already started the process in New York and Nebraska. After that he said he’ll begin working in Pennsylvania and Ohio.

If you live in the Boston area and eastern Massachusetts, you may find all of this hoopla about Route 20 to be a head-scratcher. Route 20 is the road that Waze tells you to take if there’s an accident on the Mass Pike. After the tony suburbs of Boston, Route 20 can get, to be polite, downright bland. But then the character of the road begins to shift. In Sturbridge and Brimfield there are blooms of black-eyed Susans, Queen Anne’s lace, and tiger lilies lining the road. There are quaint antique stores, and, well, there’s a bar with topless dancers in Palmer. But let’s call it a gentleman’s club and make it sound like a charming throwback.

A festive dinosaur greets passers-by outside an antiques store.
A festive dinosaur greets passers-by outside an antiques store.Christopher Muther/Globe staff

After talking to people about Route 20, I decided to drive it through Massachusetts. There are towns where it’s idyllic. The highway is 153 miles from Boston to the New York border. Sadly I didn’t have time to drive it across the country. I put my Route 20 emphasis on central and western Massachusetts. It winds through an impressive and historic stretch of downtown Springfield (also near the new MGM casino), then past Westfield it becomes truly special.


Have you ever taken the time to drive through Russell, Huntington, and Chester? These are bucolic towns with attractions such as the Huntington Country Store (home of the wrapple!) and the Keystone Arch Bridges Trail in Chester. It then continues to Jacob’s Pillow in Becket and Shaker Hancock Village in Pittsfield. If you’re interested in road tripping Route 20 through Massachusetts, or across the country, Farr has guides on his website (historicus20.com).

According to State Representative Tricia Farley-Bouvier, a Pittsfield Democrat and one of the sponsors of the bipartisan Route 20 bill, the designation would likely be most beneficial to small towns and businesses along 20 in western Massachusetts.

“What I’m understanding is that there’s this whole movement of people who really want to be off the beaten path,” Farley-Bouvier said. “It’s an experience to go off the Pike and kind of meander and learn about these quiet towns. There’s some pretty amazing things on Route 20.”

Farr knows all about amazing things along Route 20. After that initial 2010 plan of a one-time road trip, he drove the route a second time. He’s also made it as far as Wyoming six times, and Iowa 12 times.

“Every town has a story,” he said. “You drive into a small town and you think you’ll be there for an hour, and it ends up being four hours because there’s so much history, or just very talkative, friendly people. But this is what I hope people find on Route 20. It’s not just getting from point A to point B. It’s about hearing the stories of what the country is all about.”


Christopher Muther can be reached at muther@globe.com. Follow him on Twitter @Chris_Mutherand on Instagram @Chris_Muther.