Robbie Robles traces his culinary roots to his grandmother (Amá), who has French roots, and his mother, who was born in Guadalajara, Mexico, and grew up in California with six sisters and one brother. “There’s an amazing culinary tradition there, with incredible French, Lebanese, and other influences,” he explains. “Chef Enrique Olivera’s Pujol in Mexico City is consistently ranked one of the top restaurants in the world… You’ve never tasted anything like French Mexican bread.”
Robles remembers, “Growing up, I was always working with my mom in the kitchen, making something out of nothing.” His mom was 17 and living in Santa Monica when he was born. They moved to Sheffield when Robles was nine, after his mother met—and fell in love with—her sister’s brother-in-law on a visit to the Berkshires.
Between the six sisters, there were many keepers of recipes. “If you wanted to make chili con carne, you asked one aunt; if you were making chilaquiles, you asked another,” he says. Spending time steeped in cooking and family traditions contributed to his conviction that food was a very special thing. “Everything I learned, I learned at the table—stories, recipes, community,” Robles acknowledges. That realization formed the underpinning for everything he’s created in his restaurants.
Passion and persistence at an early age
During middle and high school (at Mount Everett and then Monument Mountain as a senior), Robles was into wrestling and a star on the varsity team. He placed second in western Massachusetts in eighth grade and came in first as a freshman, pinning all opponents in less than two minutes and remaining undefeated.
He also took up acting, playing lead roles in “Much Ado About Nothing” and “Hamlet” in the annual Shakespeare Fall Festival, a collaboration with local schools. When he was 16, he got an agent and picked up parts on “Law & Order” as an extra. At 17, he was promised the lead role in a new Beastie Boys movie, “Of Toys and Kings,” but the movie wasn’t fully funded and never made it to the theaters.
Turning his attention to other ventures, Robles started in the restaurant industry, working at The New Boston Inn in Sandisfield, recognized as one of the oldest inns in the Berkshires (established in 1737). He learned early on to keep a deck of cards in his pocket and pull it out to perform magic tricks to entertain guests who were waiting for an order.
A life-changing role
At 21, Robles became a father—a role that changed his world. “My son made me realize I needed to get serious and inspired me to keep going in this business,” he says, adding, “He is my world and is a big reason why I am where I am now.”
Dave Renner at The Marketplace Café in Sheffield took Robles under his wing for many years. “Dave trained with Daniel Boulud, the French chef, and opened up a lot of hands-on learning for me under his guidance,” he says gratefully. Renner’s vision and expert team brought fast-casual style dining to the Berkshires, and gave Robles an invaluable introduction to marketing and running a business. The Marketplace now has four locations (the original in Sheffield, one in Pittsfield, and two in Great Barrington). “As general manager, I learned how to take a sandwich, break it down in terms of food costs, and write it up in the manual so we could guarantee consistency every time we made it. I also practiced Anthony Boudain’s ‘economy of space,’ paying attention to what containers we used, how stations were set up, and other details to ensure the best workflow.”
Robles’s goal is always to view things from the customer’s perspective so things run smoothly—and relies on careful, consistent, hands-on training to ensure that employees follow suit. “I’ve been running with that for a very long time,” he shares, “and it’s paid off.” He also likes bringing new technology into his spaces to help make the customer experience more efficient. “So much more goes into training people now,” he admits, noting the importance of paying attention to food allergies, providing gluten-free alternatives, and scrutinizing quality and where you source your food.
When COVID hit, Robles never stopped working. “I didn’t miss a day. I was working 24/7, overseeing three operations with Marketplace. At that time, we were mostly selling prepared foods. I had to adapt quickly, and built out my own POS system through Square so we could offer online ordering,” he recalls. But far from being a negative experience, he looks back on that period proudly as a time of “high management and building great teams.” He also started posting videos on his own Instagram feed, conducting livestream interviews with people from Barrington Roasters, Harney & Sons, and the local health department (among others). “We even had our own jingle,” he smiles.

Breaking away
In May 2021, he opened his own restaurant, Roberto’s Pizza in Sheffield, which quickly became a Berkshire favorite featuring locally sourced ingredients, superior sauce and creativity, and his signature brick oven. “I went to Brooklyn and Staten Island to learn how to make the perfect pizza from the best (Andrew Scudera and Scot Cosentino),” he notes. “The secret ingredients are the base (three-day cold-fermentation dough, knuckle-kneaded) and the heat (700-plus degrees).”
Rather than rest on his success, Robles has been growing his brand ever since. “I work around the clock and am involved in everything from designing to cooking to directing the details,” he states, adding, “We’re always working on developing something cool and new.” Robles is equally meticulous about his branding, describing his logo, designed by world-renowned cartoonist Brett Parson of BlitzCadet fame (who does all of Robles’s artwork), as a “newer age Big Boy.”

Having established a name for himself with Roberto’s, Robles first expanded by adding a catering business, using a portable wood-fired oven. That business quickly grew to at least two catering jobs a week on top of the six days of restaurant hours. Last fall, he broke down the wall between his existing restaurant and the space next door to create The Pub, increasing his seating capacity (with additional picnic tables out back) to over 100.

The push
He is now poised to open a third business—dubbed Robbie’s Community Market—at the former Gorham & Norton package store (275 Main Street in Great Barrington), which opened in 1911 and continued under the Tracy family for three generations. There, he plans to offer sandwiches and pizza for on-site dining and take-out, along with a curated selection of local products.

“I have a great partner going into this project,” he confides, referring to Marc Mallett of Steadfast 413 LLC, who posted: “After a chance encounter in which I expressed our interest in supporting local entrepreneurs, one thing led to another, and we are launching a business with local restaurateur, Robert Robles. Robbie is more than an incredible chef and businessperson, but a truly unique individual who we are very excited to partner with. We are still in stealth mode, but the plan involves showcasing the vibrant Southern Berkshire food culture in downtown Great Barrington.” They officially took over the business and lease on January 1st and immediately began renovation, exposing the original beams under the ceiling tiles and old brick behind the walls.
“As soon as you step into the space, I want you to experience a community market feel,” Robles says. Following Feng Shui principles, a curved counter on the left leads to pizza by the slice and build-your-own focaccia sandwiches, take-and-bake pizza, coffee on the right, and an expansive dining room in the back. “I was involved in every choice,” Robles says, emphasizing “every light, every color, every plug.”

Taking the mat
As a first-generation restaurateur, Robles is passionate about his work and considers himself lucky to do what he does. “Marketplace was a big community builder for me, helping me launch Roberto’s five summers ago,” he acknowledges. “And the timing was right for me to start building more community in Great Barrington.” He plans on getting a pouring license for liquor, starting with a few food vendors, and growing from there. Equinox and High Lawn Farms (both in the Berkshires) and Pastries by Hanna and Ilse Coffee (both in Canaan, Conn.) are a few of the vendors lined up so far to sell their wares at Robbie’s, with more community partners in the works.
Dom at Philip Ghi Sign Company of Canaan, Conn., will be painting the logo on the storefront glass window soon—one of the final exterior touches before opening. Local artist Isha Nelson, who painted the Puerto Rico-inspired plaster walls at his Sheffield restaurant, is again working on the interior space. Eventually, he hopes to add a mural and outside seating in the back.
“This market is very much about creating community spaces where people can gather and enjoy good food. This space is the heart of Great Barrington. The Tracy family kept it running for years, and the location, design, and vision are all focused on ensuring that it continues to be a great gathering place.”

Robles employs roughly 25 people between his various businesses—10 in GB and 15 in Sheffield (between the restaurant and catering). Asked if it ever feels overwhelming, he replies, “You have to put the work in,” he admits, adding, “Anyone trying to do anything in this industry has my respect. We need more people taking chances. It means getting educated about how to run a business, but I’m optimistic about the next generation of smart youth. We’re always evolving.”
Although he’s keeping the interior space under wraps until the doors open (“We’ll keep Bourdain’s quote up for now—things are changing by the hour!”), he promises a soft opening very soon to showcase what’s coming, and expects to ramp up in early summer. “We’re going as local as we can and keeping things to-the-bone simple to start. Check our Instagram for updates,” he urges.

Robles stresses, “It truly takes a village to pull something like this together.” Every move he’s made so far has been supported by a community looking to help him finish the job on time. From getting a bench reupholstered in a day, to carpenters moving quickly to bring his vision to life, to electrician Jeremy Wolfe checking in after a 12-hour day, he feels the love from his people and is reaping—and eager to share—the rewards. “I’m looking forward to seeing everybody in the new space and celebrating together,” he says. “Stay tuned… there’s (always) more to come.”