There’s a certain magic in the New England air when autumn arrives. The mornings are crisp, the leaves turn to fire, and every town seems to come alive with the spirit of the season. For me, there’s no better way to savor fall than by exploring the best New England fall festivals—each one a celebration of color, flavor, and community. Whether you’re a leaf-peeper, foodie, or just looking for a little small-town charm, these festivals are the heart and soul of autumn in the Northeast.
Why New England Fall Festivals Are So Special
New Englanders know how to do fall right. Maybe it’s the centuries-old traditions, or maybe it’s just the way the landscape glows in October. Either way, these festivals offer more than just pumpkin spice and apple cider (though you’ll find plenty of both!). They’re a chance to gather with friends, support local makers, and make memories that last long after the last leaf has fallen.
The Big E – West Springfield, Massachusetts
If you want to experience the granddaddy of all New England fall festivals, The Big E is it. Officially known as the Eastern States Exposition, this multi-state fair brings together the best of all six New England states. Think: giant cream puffs, craft barns, parades, live music, and a midway that lights up the night. Don’t miss the Avenue of States for a taste of local flavors and traditions from across the region.
When: Mid-September to early October
Best for: Families, foodies, and anyone who loves a little bit of everything.
Vermont Pumpkin Chuckin’ Festival – Stowe, Vermont
Nothing says fall in New England quite like pumpkins—except maybe launching them through the air with homemade trebuchets! The Vermont Pumpkin Chuckin’ Festival is quirky, fun, and pure autumn joy. Along with the main event, you’ll find live music, local food vendors, and a festive, family-friendly atmosphere.
When: Late September
Best for: Kids (and grown-ups) who love a good laugh and a little friendly competition.
Fryeburg Fair – Fryeburg, Maine
For a taste of classic country fair fun, head north to the Fryeburg Fair. This beloved Maine tradition features agricultural exhibits, blue-ribbon baking contests, a bustling midway, and the famous Woodsmen’s Field Day. It’s a perfect blend of rural charm and lively entertainment, with the White Mountains as your backdrop.
When: Early October
Best for: Animal lovers, families, and anyone craving an authentic New England fair experience.
Apple Harvest Festival – Southington, Connecticut
If you’re an apple lover, this one’s for you. The Southington Apple Harvest Festival is all about celebrating the season’s sweetest fruit. Enjoy apple fritters, pies, cider, and even an apple-pie-eating contest. There’s also live entertainment, a craft fair, and a spectacular fireworks show to close out the festivities.
When: Late September to early October
Best for: Foodies, families, and anyone who believes fall isn’t complete without apples.
Woodstock Harvest Festival – Woodstock, Vermont
Woodstock is the quintessential Vermont village, and its Harvest Festival is the perfect place to soak up small-town autumn charm. Wander through the Billings Farm & Museum, sample homemade jams and cheeses, watch traditional craft demonstrations, and take a horse-drawn wagon ride through rolling hills ablaze with color.
When: Early October
Best for: History buffs, families, and those seeking a slower, more nostalgic pace.
Salem Haunted Happenings – Salem, Massachusetts
For a fall festival with a twist, head to Salem’s Haunted Happenings —home of the infamous witch trials and now the epicenter of Halloween fun. Throughout October, Salem transforms into a spooky wonderland with parades, ghost tours, costume balls, and street fairs. It’s a little quirky, a little eerie, and absolutely unforgettable.
When: All October
Best for: Halloween fans, history lovers, and anyone looking for a little autumn mischief.
Tips for Making the Most of New England Fall Festivals
- Arrive early: Parking fills up fast, especially on peak weekends.
- Dress in layers: Fall weather can be unpredictable—bring a cozy sweater and a rain jacket just in case.
- Bring cash: Many local vendors and farm stands are cash-only.
- Take your time: Savor the flavors, chat with local artisans, and soak in the scenery.
Savor the Season
Whether you’re sipping hot cider under a canopy of maples or cheering on a pumpkin as it soars through the sky, New England’s fall festivals are a celebration of everything that makes this season special. So grab your favorite flannel, hit the road, and let the spirit of autumn carry you from one charming town to the next. These are the moments—and the memories—that make fall in New England truly unforgettable.