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There’s something about a fall festival in New England that can’t quite be replicated anywhere else. Maybe it’s the crisp air that smells faintly of woodsmoke, or the way the afternoon sun hits a row of pumpkins lined up for judging. It’s the crunch of leaves underfoot as you walk the midway, the call of the carnival barker, the sound of a country band carrying over the crowd.
But in Massachusetts, fall festivals carry more than just the joy of seasonal entertainment — they are threads in the long fabric of local tradition. They tie us to our agricultural past, to our neighbors, to our own childhoods. When you step onto the fairgrounds at Topsfield, West Springfield, or Northampton, you’re not just going to a fair. You’re stepping into a story that’s been told for centuries.
Here are three festivals that define the Bay State’s autumn spirit, beginning with the one that has shaped my own New England life more than any other.
I grew up with the Topsfield Fair as a non-negotiable part of fall. As a kid, it meant Ferris wheels, carnival games on the midway, and the smell of fried dough drifting through the crisp October air. When I moved to Los Angeles in 1996, the Fair became something even more precious — a piece of home I could return to with my two daughters. On our visits back to Massachusetts in early October, seeing family was the main event, but the Topsfield Fair was always on the itinerary.
The Topsfield Fair began in 1818, making it the oldest continuously running agricultural fair in the country. That year, the Essex Agricultural Society, concerned about the decline of farming in the region, hosted a small cattle show. It was a practical affair — a way for farmers to share breeding practices, compare stock, and celebrate the bounty of their fields.
Over the years, that modest gathering blossomed into an annual tradition. By the late 19th century, Topsfield had become a spectacle, attracting tens of thousands of visitors. Steam trains brought crowds from Boston and beyond, and the fairgrounds expanded to include barns, exhibit halls, and the now-famous midway.
Local lore holds that in the early 1900s, farmers would walk their oxen for miles just to compete in pulling contests. The oxen would drag sledges weighed down with granite blocks, cheered on by townsfolk who placed friendly wagers on which team would prove strongest. The ox pulls became legendary, and the event remains a staple today — a living link to the fair’s agrarian roots.
The Giant Pumpkin Weigh-Off is arguably the Fair’s most famous event. Every year, growers bring pumpkins the size of small cars, hoisted carefully onto industrial scales as the crowd looks on. The current world record pumpkin — weighing in at over 2,700 pounds — was grown by a Massachusetts farmer and debuted here.
There’s something both absurd and inspiring about watching a crowd hold its collective breath as a single orange globe dangles from a crane, then erupts into applause when the numbers appear. To me, it captures the spirit of the fair perfectly: community pride, quirky tradition, and a celebration of abundance.
As a kid, I didn’t care much about ox pulls or prize cattle. It was the midway — the neon lights, the smell of popcorn, the rickety rides that felt both terrifying and thrilling. Coming back as an adult, with my wife and my two now-grown daughters, I see it differently. It’s not just about the rides or the food; it’s about continuity. It’s knowing that the same fairgrounds I walked as a child are still welcoming families, generation after generation.
This year’s Topsfield Fair runs October 3–13, but you can always count on it for ten straight days ending on Columbus Day. And in those ten days, a small Essex County town becomes the heart of New England autumn.
If Topsfield is tradition, The Big E is spectacle. I didn’t experience this fair until recently, and I was floored by its sheer size and scope. It’s like all six New England states under one roof — or rather, along one “Avenue of States.”
The Big E began in 1916, conceived as a way to promote agriculture and industry throughout New England. It quickly grew into the largest agricultural fair in the Northeast, with state-specific exhibition houses lining the fairgrounds. To this day, you can stroll down the Avenue of States and “visit” Maine, Vermont, New Hampshire, Connecticut, Rhode Island, and Massachusetts — all in a single afternoon.
Each building is a showcase of local culture. The Vermont house sells maple syrup and cheddar. The Maine building offers lobster rolls. Rhode Island serves clam cakes and chowder. Massachusetts, of course, highlights cranberries and baked beans. It’s a regional smorgasbord unlike anything else in the country.
Over the decades, The Big E has developed its own lore. Politicians have long used it as a campaign stop, and musicians from Johnny Cash to Aerosmith have played its stages. Locals joke that you can measure the seasons by the arrival of The Big E cream puff — a pastry so iconic it now has its own dedicated bakery.
Some say the fairgrounds are haunted, too. The Coliseum, once home to the Springfield Indians hockey team, is rumored to echo with the sound of skates on ice long after the rink was dismantled. Whether you believe in ghosts or not, the mix of history and spectacle makes The Big E feel like more than a fair — it’s a cultural crossroads.
Today, The Big E draws over a million visitors each year. It’s an economic powerhouse for the region and a rare example of states coming together to celebrate their collective identity. In a way, it’s the opposite of Topsfield: where one is intimate and rooted in a single community, the other is sprawling and regional. Yet both capture the same New England essence — pride in place, celebration of tradition, and the joy of coming together in crisp autumn air.
We missed this one in 2025, and I’m still a little bummed. Despite that unfortunate fact, I list it here under my personal ‘top-three’. Just last year, on a warm late summer day, my wife Deborah and I made our way here with one of my best friends and his wife. I was instantly taken by the fair’s walkability — no sprawling miles to cover, just a compact, easy-to-enjoy celebration of agriculture and community. Oh, and food trucks. Lots of food trucks delivering much better than your average fair food.
The Three County Fair has its own claim to fame: founded in 1818, the same year as Topsfield, it also contends for the title of America’s oldest agricultural fair. Held in Northampton, it was originally designed to highlight livestock breeding, crop production, and the latest farming implements. Farmers would travel from Hampshire, Franklin, and Hampden counties to compete for prizes and bragging rights.
Unlike Topsfield, which quickly became known for its massive pumpkin weigh-offs, the Three County Fair retained a more grounded, small-town feel. Even today, the emphasis is on livestock shows, crafts, and local agriculture. Walking through the barns feels like stepping back to a time when farming was the center of life in western Massachusetts.
When I visited, it struck me how much the fair reminded me of the small-town festivals I grew up with — neighborly, unhurried, rooted in place. One moment we were watching horse pulls, the next browsing local crafts, and then grabbing a bite under the shade of the old trees that dot the fairgrounds. It felt less like an event you attend and more like a gathering you belong to.
Fall festivals in Massachusetts are more than events — they’re traditions woven into the fabric of the season. They bridge the gap between the last warm days and the first frost, between summer’s chaos and winter’s quiet.
For me, they’re a reminder that no matter how far life takes you — whether across the country or just to the next town — there are places and moments that remain unchanged, ready to welcome you back.
I grew up with the Topsfield Fair, and each and every year the slogan “America’s Oldest Agricultural Fair” was repeatedly drilled into my head, so I will personally give that nod to Topsfield. That being said, Massachusetts may argue with itself about which fair is truly the “oldest,” or which pumpkin deserves the crown, but what matters is continuity. The glow of lanterns against a darkening sky, the laughter over a plate of fried dough, the smell of hay in the barns — these are the markers of our season, and they’re worth coming home for.
