There’s no time quite like the fall to visit New England. Each state offers its own take on stunning foliage. From the mountainsides bursting with color in Vermont, New Hampshire, and Massachusetts’ Berkshire region to the quaint villages of Connecticut and even a stop in spooky Salem, these are among the best New England fall family road trips.
Quechee, Vermont
Let’s start our New England fall family road trip list in Quechee, Vermont. Quechee itself has the Quechee Gorge Village with shops galore. Get all your moose and bear trinkets, stop in for some Cabot cheese, and pet an alpaca or two. The Quechee Gorge hike is steep but still accessible for kids, with a wide path and gorgeous views, especially in autumn. Nearby Woodstock is always a hit, and in the fall looks like a postcard scene. With plenty of dining and lodging options here, check out Quechee and the rest of the Upper Valley for your next family vacation. The fall envelopes this region with a fireworks display of oranges, reds, and yellows.
The Berkshires, Massachusetts
Get ready to experience the beauty of autumn in the Berkshires! This region is known for its stunning fall foliage and family-friendly hiking trails, making it the perfect destination for a seasonal getaway. In the autumn, this region is all about getting out of doors. Check out the trails at Monument Mountain in Great Barrington, Pleasant Valley Wildlife Sanctuary in Lenox, or even the Ashwilitcook Rail Trail.
The Quiet Corner, Connecticut
The Northeast, or Quiet Corner of Connecticut, includes colonial villages, rugged woodlands, and vast farmland, and is best enjoyed when the autumn colors are alive and dancing. Try Route 169, beginning in Norwich and ending close to the Massachusetts border in Woodstock. In the region, pick a pumpkin or two, munch on a cider donut, and sample a glass of apple cider. Also check out the region’s array of wineries, distilleries, and breweries, many of which have a rural feel. Check out The Last Green Valley and their excellent Walktober series for a list of ongoing events in this region during October.
Salem, Massachusetts
Get ready for a blend of rich history, intriguing mysteries, and plenty of kid-friendly activities. This charming coastal city offers something for everyone, making it a perfect destination for families and history buffs alike. Let’s head to Salem for our next New England fall family road trip destination. Salem is the perfect combination of a picturesque small New England seaside city, with an independent spirit, great architecture, and, of course, many haunted attractions. Whether here to get spooked, immerse yourself in history, or enjoy the seasonal attractions, Salem is a must-visit in the fall.
Jackson, New Hampshire
Located in a valley in the midst of the majestic White Mountains, the village of Jackson is stunning in any season. In the fall, though, in addition to a spectacular site for the eyes, this small town welcomes back its annual Pumpkin People! Figures with pumpkin heads are on display throughout the quaint town of Jackson. It’s fun to walk (or drive) around Jackson, spotting as many as you can. 2025 marks the 41st anniversary of the Pumpkin People. For this year’s event, check out the map here; they anticipate around 60 participants. Past displays have included pumpkin people trick or treating, the Muppets, and commemorating the moon landing. They are on display during the whole month of October. Make sure to take a pic of the landmark covered bridge in town, too!
Whether exploring back roads of eastern Connecticut, hanging with the pumpkin folk in Jackson, New Hampshire, or seeing spooky sites in Salem, New England is chock full of fall fun. For the best New England fall family road trips, make sure to check out these regions; you’ll be “fall”ing for them soon!
For other regional favorites in the autumn, read these articles about Halloween happenings, apple picking, and cider mills.
