Stepping into Jack Gilbert’s black studio barn on Dorset West Road, surrounded by oil paintings of landscapes, sunsets, and seasonal changes from the grays of winter to the warm colors of spring, feels like walking through Vermont itself. This makes sense, given Jack’s deep roots in Dorset. 

“My great-grandfather came here in the 1850s. This road used to be called ‘Gilbertsville’ because there were about 17 family households here,” he recalls. As a kid, Jack milked cows and baled hay at Junior Nicolas’ dairy farm. “Every summer we’d bring in hundreds of bales for the 150 sheep.” He also pruned apple orchards on his grandfather’s farm, where apple production was a thriving business in the 1940s and 1950s, alongside a large chicken coop that supplied eggs commercially.

Jack left Dorset for a time, earning a BFA (1976) and an MFA (1982) at Rutgers University before pursuing a successful career as an artist in New York City, helping make ends meet by doing front-of-house work in high-end restaurants. However, Vermont was always in his heart, and Jack and his family returned to Dorset in 1993 after his first son, Bill, was born. Dorset offered a simpler life where his sons (a few years later, his second son, Cody, was born) could play outside with close friends, neighbors, and family. 

Figuring out how to make a living in Vermont, Jack briefly worked for upscale furniture makers while toying with the idea of opening a restaurant of his own. He recounts,“The restaurant world 30 years ago was very different. There were no Thai places; no ramen shops; Mexican cuisine was slowly growing nationally.” Given his experience in high-end restaurants in New York City and having worked as the general manager at Rosa Mexicano, regional Mexican cuisine was a logical choice. 

Canderleros opened in 1995, offering what was, for the time, adventurous Mexican cuisine; however, balancing his background in high-end dining with local tastes was a lesson in adaptability. Over the years, Canderleros gradually evolved into a more relaxed, welcoming, and community-friendly restaurant, renamed Gringo Jack’s in 2009. Coincidently, that laid-back vibe is in harmony with Jack’s calm, matter-of-fact demeanor - unlike the intensity of restaurant kitchens where he cut his teeth. “I used to work in high-pressure restaurants in New York. If you’ve seen The Bear, it’s like that—I watch it and get PTSD,” Jack says.

Over the years, Jack has done nearly every job in restaurants, starting with dishwashing as a teenager at the Sirloin Saloon to working as the chef/owner for 10 years at Gringo Jacks. Currently, Jack is the “guiding force” behind Gringo Jacks and goes in most days to oversee daily operations.

In the early mornings, Jack spends time in his studio before the restaurant gets busy. There, he often works from photos or small sketches; he describes his painting process as a collaboration with the work itself. He explains, “I know when a painting is done when it stops asking me to change it. When I can look at it and feel like it’s arrived.You can overwork a painting. You can pass by several great versions and end up ruining it. I’m not trying to replicate an image. I’m making a painting.”

Jack remains connected to the landscape he describes as incredible. That connection to - and his deep observation of - the land comes through clearly in his work. On the wall of his studio is an arresting painting of a forsythia in full bloom. “Forsythia bushes don't really look that yellow,” he says, “but they make you feel like they are that yellow”. That kind of awareness comes from truly knowing a place - not just how it appears, but how it feels to be in it. In Jack’s case, that place is Dorset. 

Jack Gilbert 

802-345-0836