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We are officially in leaf peeping peak, here in New England and come Columbus Day weekend you’ll start to see buses full of leaf peepers traveling the scenic roads of New England throughout the month of October. With that being said traditional leaf peeping spots like Woodstock in Vermont, White Mountains Range in New Hampshire and Historic Route 7A near Manchester Vermont; might become harder to get to and definitely will become more crowded so in today’s post, I’m sharing our 5 Best Leaf Peeping Picnic Spots in Massachusetts!

For some reason, leaf peepers will often start in Litchfield County CT and skip over a chunk of Massachusetts in hopes of catching the magnificent leaves in Vermont and New Hampshire. Year after year I see Massachusetts get left off of almost every leaf peeping guide, and to be honest I really don’t know why. Between New England’s quintessential historic towns and the marvelous city of Boston, Massachusetts has just as much to offer as it’s fellow New England states. So let’s get right to it!

5 Best Leaf Peeping Picnic Spots in Massachusetts:

Deerfield, MA: This town is picturesque come fall and is, in fact, the backdrop to many of our most iconic fall photos. From the historic homes to the giant historic maple trees, this town is filled with brilliant colors of orange, red and yellow. With plenty of parking and Yankee Candle factory not too far away, this town is the perfect place to throw down a plaid blanket and enjoy an afternoon lunch. 

Salem, MA: Put a little thrill into traditional leaf peeping with a stop at Salem, MA. This spooky seaside town will definitely be on the busier side, as tourists come from far and wide for the towns famous haunting attractions come October. Salem, home to the infamous Salem Witch Trials back in 1692, will sure to give you a spook and a scare if you dare to visit. 

Beacon Hill, MA: If you’re heading to Boston and don’t have time to leaf peep outside of this historic city, don’t fret because one of my favorite leaf-peeping picnic spots is just within the city. Grab a blanket and camera and head to the cobblestoned streets of Beacon Hill, here you’ll be sure to find several stunning alleyways covered in yellow crisp leaves. Once you’re all leafed out, just head to Tatte’s Bakery to snag a sandwich and walk just 5 minutes across the street until you hit The Boston Public Garden. Here you’ll be able to picnic with plenty of space and more gorgeous views of the city.  

Lenox, MA:  You haven’t seen a true fall in New England until you’ve visited the Berkshires. I recommend visiting the Berkshires by car, and would highly recommend driving up either Route 7 or Route 41. Both of these routes will lead you to Lenox, MA and many other historic towns worth exploring. Along the way, you’ll be sure to pass several family-owned delis, snag a sandwich; next at your leisure just stop at any designated scenic photo parking spots for your picnic with a few. 

Sturbridge Village, MA:  Located in Worcester County, Massachusetts, Sturbridge Village is the ideal leaf-peeping spot for couples traveling with kids. Break up your leaf peeping road trip with a stop at the largest outdoor history museum in the Northeast. With hands-on activities and get to see what life was like for New Englanders in the 17th century. While there is plenty of places to picnic inside Old Sturbridge Village, I also highly recommend eating at the historic Publick House just a few miles away. It’s one of my favorite restaurants in all of New England. 

That wraps up our 5 best leaf peeping picnic spots in Massachusetts. With that being said, I’d love to hear from you all what your favorite fall picnic food is? Mine is Louis Jadot wine and apple crumb donuts, can you blame me! 

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