Beautiful Scenic Drives Around Pittsfield, MA

Pittsfield, MA, is the perfect spot for a scenic drive! From backcountry byways to pretty overlooks, the itinerary practically writes itself here. Let's put the keys to a perfect afternoon in your hands with a roundup of the best scenic drives near Pittsfield, MA.

The Mohawk Trail Scenic Byway

Bringing you through the stunning Connecticut River Valley and the Berkshire Mountains for 69 view-filled miles, this well-traveled route has a deep natural history and a close connection to New England culture. While the road is paved today, it was once a Native American footpath. As you cruise the byway, you'll see stretches of the Millers River, Cold River, Deerfield River, and Hoosic River. You'll also pass through the towns of Greenfield, Buckland, North Adams, Athol, Orange, Erving, and more. A highlight of the byway is that it actually brings you right through the quaint downtowns of several "classic" New England towns. If you're planning to get out of the car for some fresh air, choose biking the trails at Thunder Mountain Bike Park or hiking through Mohawk Trail State Forest.

Jacob's Ladder Trail (Route 20)

This 33-mile route is perfect if you love a rural byway that pays off with access to some of the most popular Berkshires landmarks and museums. Bringing you along the idyllic Berkshire foothills, this byway takes you through views of vistas cropping out from dense forest, ragged cliffs, rocky rivers, gorgeous meadows, and picture-perfect small towns oozing with New England charm. If you're looking to work a hike into the day, stop at Chester-Blandford State Forest to explore some trails. In the winter, the forest is a popular spot for snowshoeing and cross-country skiing. Some other notable stops to add to your day include Becket's historic granite quarry, Jacob's Pillow National Historic Landmark District, Edith Wharton's The Mount, and Ventfort Hall, a Gilded Age mansion and museum.

Mount Greylock Scenic Byway

If your goal for finding the best scenic drives near Pittsfield, MA, is arriving at the best view, this 16-mile route is a dream come true! This is your chance to see what the world looks like when you're sitting at the top of the tallest mountain in Massachusetts. Offering more than 70 miles of trails that dip into the Appalachian Trail for 11 miles, Mount Greylock State Reservation offers opportunities to enjoy views from your car or get out to hike for a bit. Visit the Mount Greylock State Reservation Visitor Center, take in the views from Mount Greylock's summit, or simply glide along in your car until you hit the next village. Mount Greylock offers views up to 70 miles out, covering five states!

Don't Skip the Peace and Beauty of a Scenic Berkshires Drive

A long drive to clear your mind and appreciate nature is like nothing else! The best part is that the roads and byways stay lovely here all year long. There's fireworks-like foliage in the fall, flower-filled meadows in the spring and summer, and a snow lover's paradise in the winter! You'll also have plenty of reasons to get out of the car for a bit to explore recreational parks in Pittsfield, offering trails, gardens, playgrounds, splash pads, and more.