There are two ways to fall in love with fall in Massachusetts. One is heading out west to the Berkshires and leaf peeping along the 63-mile Mohawk Trail, New England’s original scenic drive (and arguably Massachusetts’s most picturesque). The two-lane highway follows a Native American trade route as it passes through 50,000 acres of preservations and forests including the Mohawk Trail State Forest, where bears and bobcats have been known to cross the road. For a good hike, detour up to North Adams to climb Mount Greylock, the state’s highest peak at 3,489 feet.
The second option is sticking to the Bay State’s capital, Boston, and taking in autumn at easy-to-reach and easier-to-photograph spots while eating your way through the season. Get your fix of fall bliss strolling the Public Garden, the Charles River Esplanade, up the iconic Acorn Street in Beacon Hill, or through the Arnold Arboretum. Better yet, consider taking a ride out to the trails around Walden Pond or Middlesex Fells Reservation–both just minutes outside the city proper–and blow up your Instagram feed with shots of the foliage reflecting off the water. Pack in as many steps as possible, since you’ll also be feasting on the seasonal harvest at Boston’s best restaurants.
Where to stay
Take in the best of the northern Berkshires from the Williams Inn–an adorable, refined property just minutes from MASS MoCA, the Clark Institute, and gorgeous New England forest as far as the eye can see. Craving something a little more Scandinavian-inspired, contemporary and vibey? Check out the hip Tourists.
In Boston, get the foliage experience from the comfort of one of the city’s best hotels: The Newbury, which overlooks the splendid Public Gardens. Time your stay right for mid- to late-October, book a park-facing room, and you’ll be able to take in all the colors from the comfort and privacy of your bed.
Where to eat
Not every dinner needs to be a chef-driven, fancy affair. Embrace the motor lodge, grassroots history of this part of Massachusetts with a bite at Jack’s Hot Dog Stand, which first opened its doors in 1917. You can still get a plain hot dog for an impressive $1.95. That leaves you with plenty of gas money for a long, winding road trip while taking in that Berkshires foliage. Speaking of essential snacks in the region, no road trip here is complete without picking up a bag of apple cider doughnuts from the family-owned Bartlett’s Orchard in Richmond.
On the other end of the Bay State dining spectrum, why not indulge in a little fine dining over in Boston? The food at iconic local favorite Bistro du Midi is just as classic and spectacular as the views over the Public Garden. Be sure to splurge on chef Robert Sisca’s Ora King Salmon Crudo, which comes dressed with morels, pear, jalapeño, and a rosé gratiné. C’est superbe.
