January 27, 2023

I have to admit that road trips are a constant in my life. When driving upstate, central and west New York, I avoid The Thruway at EVERYONE cost as “DUTY FREE” The road section brings some substance to the ride and again a slice of Americana awaits me as the journey takes me through farmlands and quaint villages that truly embody the simple life.

The street I am referring to is US Route 20 which spans over 3,300 miles from Boston, Massachusetts to Newport, Oregon. It is considered the “LONGEST” road through the continental United States. I highly recommend an upcoming excursion, but you don’t have to go that far as this famous stretch of road runs right here in the Berkshires and ends in the Bay State capital.

Here are three “must stop” places if you embark on a piece of that 153 mile journey here in our backyard:

Naumkeag Facebook

Naumkeag Facebook

One of your obligatory stops in the Berkshires is the village of Stockbridge, home of Naumkeag, a historic Gilded Age mansion that is an architectural masterpiece and the flora is absolutely stunning. Sit on top of a hill for a breathtaking view as this stop is on the National Register of Historic Places. The locale really offers a nice way to appreciate South County’s rich history and beauty. It’s a slight detour off Route 20 as you head south on Route 7 to Prospect Hill Road. Log on to the Naumkeag website for more details.

19th century illustration

Getty Images

Forget riding The Mass Pike (save money for starters) and continue on “toll-free” Route 20 as you travel east about 77 miles, where you can travel back in time on the popular route Old Sturbridge Village. This museum really takes you back in time as you experience life in New England in the 1830’s. Many of these buildings originally date from the 19th century, including mills, residences, a schoolhouse, meeting house, bank, farm and more. You will be taught by costumed interpreters who will also present demonstrations and re-enactments as this period of history is kept in fashion. They are open all year round. To schedule your recommended visit, log in to the site here.

Boston, Massachusetts, USA skyline over Boston Common.

Sean Pavone

Last stop: The 72-mile hike to bean city (via Route 20), where you can learn about some of the city’s historic sites, including the Old North Church, one of many fascinating Revolutionary War sites that still stand. Visit Bunker Hill and Granary Cemetery, where historical figures such as Paul Revere and Samuel Adams are buried. While in Boston, grab a big bowl of clam chowder and dine at the variety of restaurants, and for sports enthusiasts, the Red Sox, Celtics, and Bruins await (just bring some extra spending money, you’ll get the view of the Atlantic is also magical.

BOTTOM LINE: East OR West, a drive down this legendary road is “unforgettable in nature”. Don’t forget to take some unforgettable photos during this once-in-a-lifetime trip. I’m sure you’ll thank me!

LOOK: State-by-state Route 66’s most whimsical and beautiful attractions

Stacker has compiled a state-by-state list of 50 attractions to see along the driveway, drawing on information from historic sites, news, Roadside America and the National Park Service. Read on to find out where travelers can have fun on Route 66.

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