CUMMINGTON — The Cummington Fair, a long-standing agricultural tradition dating to 1869, is like a centuries-old clock: It takes a slew of gears to keep it running, and its arrival signals to many in the Hilltowns that summer is drawing to a close.

From board president Albert Judd to longtime volunteer Larry Mason to the fair’s next generation of leaders, the people who keep the Cummington Fair running span decades — and their work rarely stops, even when the fairgrounds sit quiet the rest of the year.

Each year, 60 to 70 volunteers keep the tradition alive, putting in countless hours to maintain the fairgrounds and run the annual event. While the fair itself lasts only four days, the work behind it continues nearly year-round. There is always grass to mow, painting to do, siding to replace, and larger projects to tackle, including updates to the fairgrounds’ electrical infrastructure.

The board of directors is made up entirely of volunteers and meets 11 months of the year to plan, organize, and advertise the fair. Last Saturday morning, a handful of volunteers put up fencing for the popular demolition derby as the fairgrounds prepared for another year.

The fair draws visitors from Boston, Maine, and communities throughout New England, and will begin Aug. 27 and run through Aug. 30. For a detailed schedule and more information, visit https://cummingtonfair.com/.

Albert Judd, president of the Cummington Fair, grabs a piece of wood at the Cummington Fair Grounds last Saturday. The fair kicks off Thursday and runs through Sunday, but some 60 volunteers work to plan and get the site ready year-round. DANIEL JACOBI II / Staff Photo

From the outside, the fairgrounds can look dormant for much of the year. But Albert Judd, the fair’s president and a Goshen resident, said there is always work happening behind the scenes.

“The bee’s nest is working inside,” Judd said.

In some years, the fair spends between $50,000 and $100,000 on maintenance and infrastructure alone, Judd said. That does not include entertainment or the cost of putting on the fair itself, which can run at about $50,000.

The fairgrounds are also used for roughly a dozen events throughout the year, including weddings, anniversary parties, bicycle races and animal events. Those events help generate revenue, but the fair also benefits from investments made by previous generations of organizers, Judd said.

Previous generations put a lump of money into the stock market, providing a constant source of revenue.

“We stand on the shoulders of giants that came before us,” Judd said. “If the foresight wasn’t there from the generations before us, we’d really be hurt.”

But the fair’s financial challenges have grown in recent years, organizers said. State funding that once helped pay premiums for exhibitors — from vegetables and children’s projects to livestock — largely disappeared about 15 or 20 years ago.

The Cummington Fair now pays roughly $40,000 to $45,000 in premiums each year, said Judd.

“That’s just award money for your best zucchini or best show cow or, you know, first place oxen or all that sort of stuff,” Judd said.

The state has provided some grants in recent years, including money following the COVID-19 pandemic and grants for infrastructure improvements. But the bulk of the work remains in the hands of volunteers.

Like all the fair’s volunteers, Judd needs to balance his work life and fair life. His work with the fair is in addition to running his family’s stone quarry in Goshen. Among the business’s recent projects is supplying Goshen stone for a retaining wall at the new, yet-to-open Veterans Home in Holyoke.

Judd said he is usually up around 4:30 or 5 a.m. and often stays up late. But the volunteer work has its own rewards.

John Bird grabs a roll of fencing at the Cummington Fair Grounds last Saturday. DANIEL JACOBI II / Staff Photo

“You gotta enjoy it,” Judd said. “That’s the fun part of just being a group of volunteers. They’re not here because they need a paycheck. They’re here because they enjoy it.”

“It’s a second family,” he added. “It really is.”

The fair is a gathering place for families who have attended for generations. Some return to see their family’s exhibits. Others come to see animals belonging to friends or relatives, ride the rides, eat fair food and see people they might encounter only once a year.

For Larry Mason, who has volunteered for about 30 years, the fair has been a staple of his life since childhood. He was raised on a farm in neighboring Worthington and showed sheep and cattle at the fair as a youth. His daughter later did the same, while his wife served as the fair’s treasurer for several years.

“The fair has just kind of been in our blood for years and years,” Mason said. “There’s a lot of work to keep everything up here because everything needs work.”

Kenneth “Trudge” Howes, chair of the Cummington Select Board, drove a tractor Saturday morning, hauling mesh fencing while a group of volunteers drilled into the ground to install posts.

Trooper, the dog, walks around as John Bird, left, and Kenneth “Trudge” Howes place fencing at the Cummington Fair Grounds, last Saturday. DANIEL JACOBI II / Staff Photo

Howes noted that volunteerism runs deep in local families, including his own, which has participated in the fair for four generations. He added that an influx of younger volunteers has given longtime participants hope that the tradition will continue.

“They just keep me along for advice — my years of knowledge from being here,” Howes said. “But they keep changing everything every year, so I get all screwed up.”

Over his lifetime, Howes has watched the fair grow, adding new events and attractions while attendance has remained relatively steady.

“It puts Cummington on the map,” Howes said.

For Howes, one of the best parts of the fair is the chance to reconnect with people he may not see throughout the rest of the year.

“A lot of people I know that come to the fair, they come once a year and hope to see someone they haven’t seen,” he said. “There’s a lot of familiar faces … but you see people you haven’t seen in a year or two, so you get to talk to people.”

“That’s, to me, what I like about it,” he said.

And then there is the food.

“Everybody eats so healthy until it comes fair time,” Howes said. “It goes right out the window. You eat every greasy thing you can think of.”

Larry Mason, back, places a flower box down at the Cummington Fair Grounds last Saturday. The fair kicks off Thursday and runs through Sunday, but volunteers such as Mason work to plan and get the site ready year-round. DANIEL JACOBI II / Staff Photo

Jared Taylor, an Ashfield resident, represents the up-and-coming generation of fair leadership. The fair became a part of his life when he was just a teenager.

“I came quite a while ago now. I took over for Tom Carter. He was the superintendent of livestock before I was,” Taylor said. “He got me involved in it. I was probably 16.”

Taylor worked with Carter in the livestock area for about five or six years before joining the board. When Carter eventually retired from the board, Taylor took over his position.

For Taylor, the fair has become a fixture of the year.

“It’s a constant. It’s always there. It’s like a part of your summer,” he said. “To me, when Cummington Fair hits, that’s when you know summer’s over.”

The fair’s appeal, he said, comes in large part from the people who make it happen.

“It’s a tradition, and it’s a great group of people,” Taylor said. “Everybody gets along, and everybody works together, and you just get it all done.”

Taylor said much of his work happens around the fair itself, rather than on a strict weekly schedule throughout the summer. He also attends meetings and events organized by the Massachusetts Association of Fairs and Agricultural Societies, where fair organizers share ideas and learn from one another.

“That’s the neat part about the Mass Fair Association,” he said. “You can talk to other fairs and see what they do.”

The gatherings give fair organizers a chance to compare what works, learn from other organizations and share their own experiences.

“It’s kind of neat,” Taylor said. “It’s kind of all fairs communicate with each other.”

Taylor also serves as the fair’s superintendent of livestock, overseeing the animals on the grounds, including the horse and oxen events. The responsibilities of the position have changed over the years, he said, but the work remains manageable because of the people involved.

“We have a good group of people, and everybody works good together,” Taylor said. “Usually, it goes pretty smooth.”

Samuel Gelinas is the hilltown reporter with the Daily Hampshire Gazette, covering the towns of Williamsburg, Cummington, Goshen, Chesterfield, Plainfield, and Worthington, and also the City of Holyoke....