Get ready for the ultimate Berkshire road trip


Hitting the road is a perfect way to explore new or familiar territory and the most important factor is the company in the vehicle as it is a perfect opportunity to meet up with family or friends. With winter just around the corner it’s highly recommended that a long and productive drive should be on your agenda and there are some scenic destinations to be found right here in the beautiful Berkshires. Let’s see where in our area you can experience an amazing trip in our backyard:


According to Triple A, they have voted this 70+ mile road one of the BEST places to explore the countryside here in the Berkshires while driving through historic towns, lush forests, state parks and water views. Highlights of this trip include a stop at the village of Shelburne Falls and a bird’s eye view of the Deerfield River.


Jesse Volodyka

Jesse Volodyka.

(Chester Village photo courtesy of Google Maps)

A GREAT alternative to the Mass Pike, this section of Route 20 is “toll-free” and offers a slice of Americana during your 33-mile hike that begins in “Lovely Lee” and ends just outside of Westfield. When heading east I like to do this tour of quaint villages that includes a passage through ‘beautiful’ Becket, Chester, Huntington and Russell before ending in the town of Westfield. This stretch of road is a quiet drive with no traffic lights to interrupt your journey, and has been described as one of the Bay State’s “picturesque back roads,” with plenty of stops to pique your curiosity, including the Jacob’s Pillow Dance Festival and the Chester-Blandford State Forest.


Wikimedia Commons

Wikimedia Commons

This 65-mile Route 2 journey begins just outside of North Adams, where you’ll encounter Berkshire County’s “hairpin bend,” which offers scenic vistas of Mount Greylock (the state’s highest peak), Mount Prospect, and Mount Williams features with mandatory stops at Old Greenfield Village, Tannery Falls, Whitcomb Summit and Barton Cove Recreation Area in the hamlet of Gill. Your final stop on this delightful drive takes you to the town of Greenfield.

Jesse Volodyka

Jesse Volodyka

(Greenfield photo courtesy of Google Maps)

BOTTOM LINE: You can still do the ultimate day trip before the arrival of old winter which is NOT that far away, but we are technically in the fall through the end of December!

APPEARANCE: Stunning vintage photos capture the beauty of America’s national parks

Today, these parks are located across the country in 25 states and the US Virgin Islands. The land surrounding them was either purchased or donated, although much of it was occupied by Native Americans thousands of years before the founding of the United States. These areas are protected and revered as educational resources about nature and places of exploration.

Keep scrolling for 50 vintage photos that showcase the beauty of America’s national parks.


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