Eleven generations and 378 years later, his field-weary descendants - arthritic from picking fruits and vegetables and battered by competition from supermarkets and pick-it-yourself farms - are selling their spread, which is among the oldest continuously operated family farms in America.
"We've been here for 40 years, doing what we love to do," said Lucy Tuttle, 65, who runs the 134-acre farm with brother Will. "But we're not able to work to our full capacity any longer, unfortunately."
Tuttle added that she and her brother and their sister have done their best "to lovingly discourage" their children from becoming generation No. 12. "We would be saddling them with a considerable amount of debt," she said.
According to eyewitness accounts, John Tuttle was shipwrecked off the Maine coast before arriving at his land grant, which boasted a mature stand of white pine trees. He cut them down and farmed around the stumps, starting what would become 250 years' worth of subsistence farming by Tuttles.
Throughout, change has been a constant on the farm, which grows sweet corn, cucumbers, squash, tomatoes, and blueberries, raspberries and strawberries.
Lucy Tuttle's grandfather, William Penn Tuttle, built the original 20-acre parcel to about 200 acres, growing more produce than the family needed and selling it in nearby towns - first on a horse and buggy.
Her father, Hugh Tuttle, who was profiled in 1971 by Life magazine as the last of a dying breed, developed irrigation ponds on the farm and was well-known in New Hampshire for his interest in soil and water conservation work before his death in 2002.
Lucy and Will Tuttle, who grew up in a 1780 farmhouse built by family members, didn't spend their whole lives on the farm.
She lived in Paris for seven years, teaching English. He went to work for an auto dealer in Boston, then worked at Campbell Soup Co. as a sales representative.
She remembers her father contemplating selling the farm.
"I think he felt discouraged," Lucy Tuttle said. "All of a sudden, the three of us came flocking back with our energy."
When they took over, Tuttle and her brother made changes, turning the farm into a year-round business instead of a seasonal one. They built a a new farm stand to replace the family's old red barn - now used for storage - and diversified the product offerings to include gourmet cheeses, baked goods, plants and other products.
"They changed their business model with the times in order to stay profitable and stay in business," said Lorraine Merrill, New Hampshire's agriculture commissioner. "It's much more than a farm stand."
But the growth of supermarket chains, the emergence of the local food movement - New Hampshire has more than 80 farmers markets - and the grueling routine took a toll.
"Eleven generations is unique," said Chuck Hassebrook, executive director of the Center for Rural Affairs in Lyons, Neb., a nonprofit policy analysis and advocacy group. "What's not so unique is that farms being operated as family farms for generations are being sold, or at least the family no longer is operating the farm."
Competition from large farms has become much more intense, whether in the Midwest - where it tends to be for land - or in New England, where it's likely to be for markets.
"That's put a lot of pressure on family-size operations," he said.
Too, the local food movement has had an impact, with consumers growing their own vegetables.
'People are getting more interested in canning, they're getting more interested in freezing food," said Juli Brussell, agricultural resources program leader for the University of New Hampshire's cooperative extension.
For years, the Tuttle farm has been referred to as the nation's oldest continually operating family farm, but it's unclear whether that's true.
News articles dating to the 1930s confirm its age, and the Tuttles said they've never been challenged over the distinction. In 1989, the U.S. Department of Agriculture said the nation's oldest farm was the Tuttle Farm, but it made no mention of the Shirley Plantation in Charles City, Va., which was founded in 1613 and was in business in 1638.
The Shirley Plantation calls itself the oldest family-owned business in North America, also for eleven generations.
Julian Charity, visitor services supervisor there, said there have been questions about whether the plantation or the Tuttle farm is older, but the plantation never challenged the Tuttle Farm over the designation.
"A couple of words can change the complete definition of a title," he said.
On Tuesday, the Tuttle Farm went on the market. Asking price: $3.35 million.
Under a deed restriction that came with its 2006 designation as conservation land, it can't be developed into strip malls or condos.
"The farm is operating until we find a buyer who loves this land almost as much as we do," said Will Tuttle, 63.
Longtime customer Linda Struble, 63, of Dover, loves the farm's corn and cried when she heard the Tuttles were selling.
She'd like to see it stay as it is. "I can't imagine anything else with it. It would be even more heartbreaking than it is now," she said.
But Lucy Tuttle says that if her ancestors could see her now, they'd be amazed.
Her sister, Becky, jokes that if John Tuttle were around today, he'd say, "What's the matter with you? Have you got no ambition? Pick up and go. I did."