I have to admit that road trips are a constant in my life. When heading to upstate, central and western New York, I avoid The Thruway at ALL costs as a "TOLL-FREE" stretch of road brings some substance to the ride and in turn, a slice of Americana awaits me as the journey takes me through farmland and quaint villages that truly embody the simple life.

The road I am referring is US Route 20 which encompasses over 3,300 miles from Boston, Massachusetts to Newport, Oregon. It has been deemed as the "LONGEST" road throughout the continental United States. I highly recommended an upcoming excursion, but you don't have to go that far as this famous stretch of road passes through right here in The Berkshires and terminates in The Bay State's capital city.

Here are three "must-stop" locations when you embark on a slice of this 153 mile trip right here in our backyard:


One of your mandatory stop-overs in the Berkshires is in the village of Stockbridge, the home of Naumkeag, a historic Gilded Age mansion which is an architectural masterpiece, and the flora is absolutely breathtaking. Set yourself atop a hill and experience stunning views as this stop has been incorporated into The National Register of Historic Places. The locale truly provides a lovely way to appreciate south county's rich history and beauty. It is a slight detour from route 20 as you head south on route 7 to Prospect Hill road. For more details, log on to Naumkeag's web site.

Illustration from 19th century
Getty Images

Forget about taking The Mass Pike (for starters it will save you money) and continue on the "toll-free" route 20 as you head east for about 77 miles where you can step back in time at the popular Old Sturbridge Village. This museum truly takes you back in time as you experience life in 1830s New England. Many of these buildings are original from the 19h century including mills, homes, a schoolhouse, a meeting house, a bank, a farm, and more. You will be educated by costumed interpreters who also present demonstrations and re-enactments, as this period in history is preserved in high fashion. They are open year round. To plan your recommended visit, log on to their web site by going here.

Boston, Massachusetts, USA skyline over Boston Common.
Sean Pavone

Last stop: The 72 mile trek to Beantown (via route 20) where you can educate yourself on some of the city's historical sites including Old North Church which is one of many fascinating Revolutionary War sites still standing. Check out Bunker Hill and Granary Cemetery where historical notables like Paul Revere and Samuel Adams are buried. While you're in Boston, have a large bowl of clam chowder and dine at their assortment of restaurants and for sports enthusiasts, The Red Sox, Celtics and Bruins have a seat waiting for you (just bring some extra spending cash, you'll need it. The views of the Atlantic ocean are also magical in nature.

BOTTOM LINE: East OR West, a trip through this legendary road is "unforgettable in nature". Don't forget to snap some memorable photos during this once-in-a lifetime journey. You'll thank me for sure!

(Some information obtained in this article, courtesy of www.historicus20.com & www.quirkytraveler.com)

LOOK: Route 66’s quirkiest and most wonderful attractions state by state

Stacker compiled a list of 50 attractions--state by state--to see along the drive, drawing on information from historic sites, news stories, Roadside America, and the National Park Service. Keep reading to discover where travelers can get their kicks on Route 66.


More From WSBS 860AM