Love Story Down
on the Farm

Jim & Annie, farm apprentices in Maine in the mid '80's

Back farming some 30 years later.

Sam and Elizabeth Smith, owners of Caretaker Farm, were heading off to Sri Lanka to lead a group of Williams College students on a Winter Study trip and they needed someone to look after their place. They hired Jim, a student at Williams at the time to care for their 1820’s era farmhouse and tend to the animals. Sam and Elizabeth’s daughter, Annie, happened to be home from college for a few days after her parents left for their trip. A romance blossomed between the young caretaker and the farmer’s daughter which would lead to a life together. They traveled to the West Coast to complete their undergraduate education, returned to Massachusetts for their Masters degrees, and ultimately came back to Caretaker Farm to raise their two children, Dylan and Sierra. In 2000, they bought a house on 10 acres in Lanesboro, MA and started a garden that would become Red Shirt Farm some 10 years later. 

Jim loves what he does


Jim has wanted to farm since he graduated high school but life kept getting in the way. He started out as a Pre-Med student at Williams College but left for a year to study small-scale sustainable agriculture at Sterling Institute in Vermont learning to work with draft horses and raise sheep. Jim returned to Williams with a new focus on environmental studies but the lure of farming was too strong and he left for good to apprentice on small farms around New England. He worked on an apple orchard in New Hampshire, a maple sugaring operation in Vermont, and a horse-powered farm in Maine before enrolling in the New Alchemy Institute in Falmouth, Massachusetts to study alternative renewable energy systems, sustainable agriculture and bioshelter technologies with some of the preeminent scientists in those fields. Jim and Annie then headed west to Olympia, Washington to complete their undergraduate degrees at The Evergreen State College. Jim helped run the student organic farm and double-majored in Ecological Agriculture and Education. The latter led him back to the East Coast to complete a Masters in Education at UMass Amherst and then into the public school classroom. With two young children, the steady income of a teacher’s salary won out over the more precarious prospects of starting a farm enterprise. 26 years of teaching, coaching and administration passed quickly. All the while Jim was reading, attending workshops and planning. With the kids out of college and on their own and the mortgage on a 10-acre property paid off, Jim decided to finally start his own farm. Red Shirt Farm.

Annie makes things happen

Annie makes things happen


As the daughter of farmers, Sam and Elizabeth Smith, Annie grew up working on Caretaker Farm in Williamstown MA, a 30-acre organic vegetable operation and one of the first CSA’s in New England. Annie also managed production and sales for a small market gardening operation in Maine for a season during the summer of 1984. Annie presently manages many of the administrative responsibilities on the farm and oversees the CSA distribution in addition to working full-time off the farm as a nurse at the Berkshire Medical Center.

Jansen's in charge

Jansen's in charge

Jansen, Super Farm Dog

Jansen is an English Shepherd who came to us from a breeder in Ancram, NY. He’s named for the Roeliff Jansen Kill, a tributary of the Hudson which flows right near his birthplace. The name was unique and fit him, so we kept it. English Shepherds were among the most common farm dogs in the 19th and early 20th centuries. Prized for their versatility, they are highly intelligent and serve as herding dogs, livestock guardians, farm watch dogs, hunting dogs, and pest eradicators. Now three years old, Jansen is showing aptitudes for all of these tasks while also being a real lover of people and animals. We think we’ll keep him.