By Carli Scolforo • Photographs by Eric Limon

As the young movers and shakers arrive on a blustery spring day and greet each other at Cantina, a cozy-chic restaurant off the beaten path in New Marlborough, the same question is asked over and over: “How have we not met before today?” Each participant comes from a different background, but their stories share an important similarity: they’ve left metropolitan areas for an idyllic Berkshires lifestyle—and brought their city-sized ambitions with them.

They couldn’t have come soon enough. While our cultural institutions—performing arts venues, museums, and Gilded Age mansions—are timeless, our population is aging. Recent census data puts the county’s median age at 48.4, and that number has been steadily climbing for over a decade. But if you’ve felt a fresh wave of energy lately, you may have this group of entrepreneurial millennials and Gen Zers to thank. We gathered 10 of these up-and-comers to talk about why they—people who could live anywhere—chose the Berkshires, what they love about the area, and the challenges they face.

Next Gen Leaders

KEVIN KELLY
Founder/CEO, After Hours Hospitality
After cutting his teeth in restaurants around Boston, Kevin returned home to the Berkshires to pioneer a new idea: a restaurant without a home. “I started with trying to open a restaurant,” said Kevin, “and decided that I wanted something nomadic.” After Hours has quickly gained a large following of foodies who excitedly await Kevin’s next pop-up at a partnering local business, where he takes over the space after the store or cafe has closed.
afterhoursgb.com

SADIE MCCLELLAND
Sales, Marketing & Design, TW McClelland & Daughters
Public relations, social media, product design—for Sadie, working in the family fine-jewelry business means doing a bit of everything. Returning home for this next chapter in her career, she feels aligned with local values. “We do slow, creative metal work that ends in really beautiful handmade jewelry that is all very nature-inspired. There’s no better place to be doing it than here.”
twmcclelland.com

ALAN PAUL
Artistic Director, Barrington Stage Company
Now in his third year at Barrington Stage, Alan has brought both major talent and fresh works, drawing from his experience in NYC and D.C. “Outside of New York or Chicago, you won’t find anywhere else with four big theaters, and Tanglewood, and all the museums,” he said of his Berkshire experience. “People come here to fill their entire summer with culture.” His season features plays on politics, history—and LeBron James and Joan Rivers.
barringtonstageco.org

A.J. ENCHILL
Executive Director, Berkshire Black Economic Council
“I love the Berkshires because it’s a place where I get to be creative. It’s a special community with really, really deep bonds,” said A.J. After returning home, he rallied local allies to support Black businesses, artists, and artisans. “We celebrate the richness of this community, and it creates this feeling of safety.” The BBEC now provides everything from hands-on technical assistance, to advocacy for public policy changes, and more.
berkshirebec.org

PETER CHAPIN
Owner, Mill River General Store & Cantina
When Cantina 226 in New Marlborough went up for sale, Peter saw the perfect chance to build on his background in agriculture and food service. “I love being in the Berkshires because I think it’s a great place to have food businesses, to start a business, and to have an audience for what you’re trying to accomplish,” he said. His love of the land and desire to support local farms and businesses have shaped his vision for Cantina’s reopening.
cantina229.com

MADELINE AUSTIN
Mill River General Store & Cantina
Prior to her current venture with her partner, Peter Chapin, Madeline feels she got the best of both worlds: growing up in the city and spending much of her professional life in rural areas. “I love this community. I really thrive around, and am inspired by, the creative energy in this area,” she said. Her passion for sustainable agriculture informs every aspect of her running the General Store, including the value of a hardworking team.
themillrivergeneralstore.com

JAMAL STOCKTON
President & CEO, 213 Ventures Corporation
Jamal returned to the Berkshires to raise a family, and brought his business acumen with him via his investment group: “We buy and build businesses, and one of the first was Tunnel City Coffee,” he said. Beyond great coffee, the purchase is just one part of 213 Ventures’ mission: using corporate experience to help local ventures grow. With a finance and engineering background, Jamal is passionate about helping underrepresented groups achieve financial freedom.
tunnelcitycoffee.com

SÖREN SMEDVIG
Musician, Music Producer/Engineer
A talented trumpet player, DJ, producer, and audio engineer, Sören is in high demand in the Berkshire music scene. Since completing his studies at Berklee College of Music in Boston, he’s helped produce three albums. This summer, he is set to DJ at prominent local galas and will soon open his own studio, Windswept Sound. “I’ve found such incredible, interesting people hidden around the whole county,” he said. “I’ve been discovering that ever since I’ve moved back.”
sorensmedvig.univer.se

ABIGAIL FENTON
Abigail Fenton Photography
Abigail has a passion for capturing memories that has taken her around the world—from Savannah, Georgia, to Hong Kong, France, and a sailboat in the South Pacific—all leading back to the place she grew up.
Her work preserves celebratory moments like weddings, launches, album releases, and many more.
“I view myself as a visual storyteller,” she said. “I love that I have access to places like Manhattan and Boston while always coming back to this peaceful area.”
abigailfenton.com

ANNE THERESE GENNARI
Speaker & Author, “The Climate Optimist Handbook”
Anne Therese, originally from Sweden, moved to the Berkshires from New York with her husband and brought her fresh take on climate communication.
“My mission is to help people shift the narrative of climate change and get excited about the future,” she said. “I feel like there is a big climate community here, and people feel very connected to nature in different ways.”
Her work includes TEDx Talks, courses, and a book praised by Jane Goodall.
theclimateoptimist.com

THE CONVERSATION

What is the hard work really like of being entrepreneurial in our community?

Kevin: A lot of getting started was just never taking “no” for an answer. Keep trying, and celebrate your failures. It’s pretty hard to do that in the moment, but you get a lot of perspective when you can accept failures and mistakes. It has helped so much with my personal development and fine-tuning of the business. Whether you are a farmer or a chef or a musician, when you work for yourself, the work really never ends. So instead of trying to go against the current, going with it is very meaningful.
Madeline: We’ve also had a lot of failures and we’ve learned from each and every one of them. To find solace when I’m wrapping my head around whatever failure is at hand, I look to the uninterrupted skyline and find a lot of peace in that. Sense of place is something I think about a lot.
A.J.: To start our business directory, I would get in my car, drive down to Great Barrington and literally knock on an entrepreneur’s glass to see if they were there. I’d get their contact information by going to Facebook or their website—borderline stalkerish. But now we have about 168 different entrepreneurs and businesses that are able to connect with each other.
Peter: You need to be a little bit delusionally positive and optimistic to start a business. When we started the farm, we had a business with zero customers, so I needed to literally go in the back door of all these restaurants and try and make some deals. That’s not easy to do and it doesn’t always work, but you have to be maniacal about what you want to do.
Abigail: As a young person, when you’re starting out, you have to do that “Berkshire shuffle.” I was working in event planning and working as an assistant, and that’s how I met people and got into venues. In our community, you really have to get out there.
Jamal: When you’re starting businesses, you’re going to get gobbled up with costs. We’re thinking broadly about the systemic problems that the community faces, that our merchants face, and how to fix those things.

Does the sense of community here help you as an entrepreneur?

A.J.: If there’s one thing that we do well, it’s working with one another, because we don’t get the same funding as our counterparts in the eastern part of the state. We rely on one another, and that’s what makes this small business-based economy really special. It’s also a green economy that celebrates the outdoors. And we do believe artists don’t have to be starving artists! They can actually have a real quality of life and have a business.
Abigail: When I moved back to the Berkshires and slowed down my pace of life, I noticed that things just flowed. I met people that wanted to hire and work with me. I’m even able to work with people who I knew as a kid and who now experience me as an adult.
Anne Therese: You can walk into a tiny coffee shop with five people, and suddenly you meet the one person who you were supposed to meet all these years. I would go to events in New York City with hundreds of people and never meet that person. I think it’s forced me to slow down and listen to where my soul is calling me, and just exist more in the everyday moment.
A.J.: That’s something that happens here in the Berkshires. You can get seen and your career can take a new trajectory just because of a new relationship. And that doesn’t happen everywhere.
Sören: There’s an incredible recording studio in Housatonic that a longtime friend owns. When I moved back here, I asked if he needed help. In New York, it’s so saturated and competitive to get into the music industry. Here, I can get past that barrier of entry and work with the high-profile artists who choose to live here to get away from the craziness of the city.
Kevin: We partner with local businesses and operate out of existing spaces during the hours that they’re closed, whether it’s a restaurant, cafe, or museum. We collaborate over competing.

While many of you have started your own ventures, others are following in family footsteps or bringing a fresh perspective to legacy institutions. What has that been like?

Alan: I feel responsible to have a successful business that operates locally. That means having good shows that fill the theater, popular concerts. But I also think that we serve a broader purpose: it’s our responsibility to put on new plays and new musicals, and to take a chance on writers you haven’t heard of. It’s so easy to do revivals of plays that are comfortable for other people, but the thing that really makes a difference are works that talk about difficult subjects, that get a conversation going, that go into something political, that challenge the form itself. It’s scary to do that because you’re taking a risk on a show that might be powerful but might not make money. I find myself sticking my neck out more than I thought. But I also find it’s fun to have the courage to do it.
Sadie: I got a degree in fine arts—I wanted and needed to make a living, and have work that is meaningful and artistic. My father has been a jeweler for 50 years, and had a business that I was very interested in joining. It’s been really fantastic to be in an artistic job, and wear so many hats under the umbrella of a family business. Having a really small business, and having a low overhead, results in endless creative possibilities.

What is something about the Berkshires environment that resonates with you?

Anne Therese: We are in a good place here and I think it’s going to become even more thriving in years to come. Climate optimism is rooted in grounded awareness, understanding, and resiliency. Instead of just trying to minimize our negative footprint, how can we step in and maximize our positive footprint? *
Madeline: I’m incredibly passionate about sustainable agriculture, particularly animal husbandry, as well as increasing accessibility. I truly believe that access to good and real food should be a core, basic civil right. That’s what led me here.
Peter: Typically, when people start a farm, it’s in the Midwest, or California, or Arizona. There are a lot of unique challenges to the Berkshires, like the cold weather. But that gives us an opportunity to focus on trying to extend the growing season in either direction as long as possible. It’s a unique but interesting challenge as a farmer, and it’s a chance to prove that, anywhere, you can grow your own food.
Sören: In the city you’re supposed to have this thriving social life. But, during COVID, I was locked in an apartment with one window—that was not doable for me. The main reason I moved back was to reconnect with nature, and have space and fresh air to breathe. I think people are starting to become more in touch with that side of themselves. Forgetting a little bit of the hustle and just breathing, you know, just being free. That’s what I identify with.
Sadie: To be doing something artistic in a place like this, it’s an endless well of inspiration. And it’s also an area that has been so historically significant for visual artists. You’re walking in the footsteps of so many people who have been making artistic work around here.
Alan: People are up for a challenge. They’re deep thinking. They are not stuck in their ways. They’re ready to be a part of something.

“That’s something that happens here in the Berkshires. You can get seen and your career can take a new trajectory just because of a new relationship.”
— A.J. ENCHILL

What’s shifting in how younger generations think about work, life, and fulfillment?

Jamal: The boomer model of working your entire life just to get to a point where you have enough money to retire as the health problems kick in—the younger generations are saying, “that doesn’t work for us.” They’re going up the corporate ladder and looking around; they’re not happy. That is a big awakening. They crave something else, crave freedom, and think, “how do I get out of this environment so that I can do what I need to be doing for myself?”
Abigail: I realized that people are spending their lives working in New York City, Boston or LA so they can afford a house to retire in and live here, and own that little business they always dreamed of. So I thought, “Let’s skip the middle step. Let’s jump right in, start living that life and making those connections now and then, in 30 years, we’ll already be here. We’ll just relax, and enjoy.”

How can a new wave of young changemakers improve life in the Berkshires?

Alan: I think the key to future happiness will be when people around our age are deciding to move up here, and craving the things that we crave: a bespoke experience at a restaurant, great jewelry, a wonderful night at the theater. And could we get a couple people to want to work for Uber? It’s such a wonderful place and it’s a secret to a lot of people. It’s not a secret to artists, though. They love getting out of the city, being in the mountains, going to Guido’s, doing the things that are really special to being here. This location is as key to their experience in the fun of the summer as the work itself.
A.J.: There’s so much opportunity that exists within the realm of economic development, but it’s figuring out how to connect what someone’s been working on day in and day out to the community of entrepreneurs. We do that in a number of different ways. The possibilities are really endless.
Peter: I’m thankful for this opportunity to meet everyone here. I didn’t actually know most of the people here before today, which is weird, right? I think that there should be more of this here. I think that would help a lot.

“When I moved back to the Berkshires and slowed down my pace of life, I noticed that things just flowed. ”
— ABIGAIL FENTON

What about the social scene?

Abigail: I grew up here and, initially, I thought I would rely on people I grew up with. To be honest, a lot of them don’t live here anymore. I really needed a new community. I got out there saying, my goal is connecting with people. And Kevin reached out to me one time and was like, ‘I want to talk about business.’ That was a really great way to connect. That intentionality is so inspiring. Plus, there’s Saturday night dancing at Hy’s.
Sören: At Doctor Sax House, a new place in Lenox, they really want to foster a younger crowd. It’s kind of a speakeasy, with a cool vibe. It’s a place to hang out.
Sadie: There’s a slowly but steadily growing opportunity to go out and socialize. Where I live, in Great Barrington, when I go to places like Prairie Whale or Mooncloud or No Comply, I end up running into people that I’ve met once or twice and connect with them.
Peter: When I moved here, Great Barrington was a totally different place than it is now. There was a little bit of a night scene and you would meet people. One thing is that all these businesses need support—Kevin’s business needs support to survive and my business needs support to survive, and I think all of ours do. And so we do have a responsibility to support each other.
A.J.: A lot of us here have a significant other. I think, for young professionals, that’s why some people will say things like, “there’s nothing to do.” What does that really mean? “I can’t find other young professionals who I would date or go out with.” That is an integral part of what will make someone stay in the Berkshires or leave. We need to figure out how to connect awesome young professionals who are in this community and are looking for someone. Because if you have that person, your forever person, you’re like, I’m good.

What is something you would like to see improve here?

A.J.: Transportation is a piece. Child care and its ever-increasing cost is a piece for sure. The housing shortage is really a supply issue in a lot of ways. As a community, we can keep our prices down and maintain the quality of life there if we’re not greedy. We understand the economies of scale and how our dollar goes much further out here. If the nonprofits are the blood of our Berkshire economy, we may as well pay them and compensate them like we do the private sector. Maybe we’ll see more people wanting to stay because they know that they can feed their families by doing something that they love every day.
Peter: Part of the trouble here is sometimes the apartments can be more expensive than in Boston or New York City—and there’s obviously a lot more to do for a young person there, and a lot more economic opportunity in some ways. There’s tons of opportunity here, but it may not always seem that way. I think that kids are leaving as a result of that perception of: “If I want to be rich, I have to go to the city.”
Kevin: Growing up through the school systems here, the narrative is really, “how do we get out?” The people who are just getting into elementary and middle school, they’re the next generation. It has to start with the people who are born here actually wanting to stay. It’s a challenge that I want to take on. I don’t know how, but I want to give those kids the perspective that there’s so much opportunity here.
Jamal: One of the things my group focused on is, how do you create more jobs that are not related to specifically the arts and music scene? We first focused on sustainability: we launched a program with the Williamstown Chamber of Commerce and Williams College focused on reusable goods. We’re thinking about how we take the raw materials from the land, like corn husk, and turn those things into cups because we think that will create jobs.
Alan: I want to see the audience get younger and younger as I get older and older. I just try to program things that I would want to see because, when you’re building a brand or your own business, you can’t fake your own taste. You have to do what you think is right and trust that if you think it’s of quality, then other people will too. B

“Being in a room with entrepreneurs and people facing the same challenges, that is a unique and a really powerful experience. We should do more of that.”
— PETER CHAPIN