Five major dairy farms populated the half-mile stretch of Upper City Road in Pittsfield where Tom Osborne’s childhood unfolded.

As he matured into young adulthood in the 1960s and 70s, the golden years of New England dairy were quietly waning in his backyard. All but one of those farms — enjoying the upward swing of technological progress in mechanical milking and refrigeration made during earlier decades — have deserted dairy, including the Osborne family, which sold its dairy cows in 1986.

Hours were long, and the work was unforgiving. Returns paled in comparison to those investments: The price of milk fluctuated with little predictability while investment grew costlier, often outweighing revenue. Towards the end of the lifetime of their dairy operation, Osborne remembers his late father, David, straining to eke out a third milking from their cows every day, one more than standard.

Resting on their shoulders was the endurance of a business already more than 200 years old. Now, the farm, founded in 1775, is marking its semiquincentennial, looking very different than how it did in the past.

“Over the years, we’ve had to evolve and not always do what we’ve always done. I think sometimes that’s a hard thing,” Osborne said. “You kind of feel like, ‘Hey, this is what we’ve always done, let’s keep doing what we do and what we know.’ But I think we’ve had to just learn.”

In 1976, the New Hampshire Department of Agriculture, Markets and Food listed 56 legacy farms as enduring within the same family of owners for 200 years. As the nation now marks its semiquincentennial, 250 years since the signing of the Declaration of Independence, only a fraction of those farm enterprises remain, pastoral gems scattered across the state.

To shoulder the caprices of the industry, most have learned to adapt.

In 1938, a hurricane made landfall in Lebanon, tearing through Ascutney View Farm, razing a four-story chicken barn Susan Cole’s father had just built. When the storm subsided, family legend tells that there were chickens stranded in trees.

“Sometimes Mother Nature decides for us,” Cole said Friday morning, representing her family farm, founded in 1771, at the New Hampshire Farm, Forest and Garden Exposition. “You have to be a flexible mind.”

Her father passed away at 102, having worked their 1,100 acres of forested and pasture land his whole life. The 100 dairy cows Cole remembers showing as a child through 4H were gradually sold, and today, the family keeps 60 sheep and taps 2,100 maple trees. Her husband manages the brunt of the manual labor, but without her full-time work in real estate, Cole said the farm would not be viable.

“Having no outside income is not an option,” she said.

Their family’s approach isn’t altogether uncommon. In 2022, farmers in New Hampshire whose primary occupation was one other than farming outnumbered farmers who made their income primarily from their land, according to the U.S. Department of Agriculture. Nearly 60% had an off-farm job that they listed as their main source of income.

For the Osbornes, bifurcating the family business proved to be a more enduring shield against the financial riptides of the industry.

While his brother Paul maintains the farm, Tom Osborne inherited from his father an expanding retail chain, Osborne’s Farm and Garden Centers, with locations in Concord, Hooksett and Belmont.

The year after the family sold its cows, they opened their first Osborne’s Agway Store, selling farm supplies. The farm continued to see changes: Their small horticultural operation has plateaued over the years; land that used to sprout corn has been seeded for hay.

Left to right: Heidi Bundy, Susan Cole and Tom Osborne, all owners of generational farms, speak at a panel at the New Hampshire Farm, Forest and Gardens Expo on Friday. Credit: REBECA PEREIRA / Monitor staff

Osborne cultivates 25,000 hay bales each season and resells more from other producers in his stores, but even the crop’s relative success hasn’t insulated the farm from uncontrollable, unpredictable challenges. The last two summers have yielded the best hay seasons in recent memory — for them and for their neighbors and competitors.

Hiring has rebounded in Osborne’s stores since COVID, but labor challenges still cast a long shadow over farm operations, especially for Heidi Bundy at Tomapo Farm in Lebanon.

Bundy knows the history of their land, inexorably entwined with the history of her family: In the mid 1800s, the family owned hundreds of sheep as wool boomed. They shifted to dairy with a herd of Jersey cows, which were displaced by black-and-white Holsteins by the time she was a child.

In 1970, her father and grandfather, by then equal business partners, reckoning with the decline of dairy, reached an impasse: either stay in or get out. They chose the latter.

During the ten years her grandfather, Howard Townsend, served as the state’s commissioner of agriculture, her father ran the farm himself, logging alone in the woods for months at a time. “We diversified, and we’ll probably continue to have to be diversified,” Bunday said.

That decisive hour came for the Osbornes’ dairy operation two years later. Around 1972, Osborne said, his father questioned whether to throw in the towel on dairy, choosing instead to prolong the inevitable.

“I think my dad, in his later years, regretted taking on more debt to stay afloat,” he said.

Their farms, generational bulwarks, have lived continuous evolutions.

The future approaches with greater uncertainty.

Of Bundy’s five children, she said none feel compelled to take on the farm. She’s promised her parents a place to live out the remainder of their days, and she’s going to “keep on doing what I can do” to ensure that she honors her word.

“If I have to leave the farm, I can do it,” she reflected. “I won’t be happy about it, though.”