Here on Cape Cod, there’s no shortage of quintessential Mom and Pop businesses, as the very essence of this unique and vibrant area offers a favorable environment for entrepreneurs to thrive. Ours is a supportive community that values local talent, and along with the annual surge in tourism, this creates a strong base for entrepreneurs to burgeon. The individuals chosen on the following pages represent the best of Cape Cod’s entrepreneurial spirit as they are passionate, resilient and steadfast in their intent to bring positive change through leadership and growth to this special place we call home. 

Anne Holden

It is immediately apparent to anyone who meets Anne Holden that her energy, enthusiasm and zest for life is infectious in the best way possible. The Duxbury-based photographer has forged a unique path in her artistic journey that elevates the ordinary into the extraordinary. A passion project on Instagram that she called Duxbury Women focused on the high percentage of innovative female entrepreneurs in the small seaside community. “I was completely struck by how many hard-working creative women there are in our local community,” she explains. “I know how important good photography is for small businesses to have. I decided to do what I could to provide affordable images, that could help with their success for these women that had put so much into their dreams.” As momentum in her burgeoning photography business grew, Shipyard Photography, the seclusion brought on by the pandemic found Holden taking porch photos of individuals and families who wanted to share and save a moment from such an oddly monumental period.

Like many during the introspective time of 2020, Holden contemplated everything she wanted to explore in her creative discovery. One of those interests included an understanding of the long-established craft of basket weaving in the iconic Nantucket-style. While attending a conference for her photography pursuits, Holden happened upon an artist weaving Nantucket bracelets. “I was immediately drawn to her, I mean mesmerized,” Holden recalls. “When I got home, I searched to see if I could find a class and lo and behold, there was one offered in Duxbury in just a couple of weeks. I mean it was just meant to be.”

Holden’s pursuit of new artistic and creative expression has been a true path of discovery as she has enrolled in various art classes through the years, but she says her exploration of basket weaving has provided her with a deep connection that she cannot ignore. “I come at it from a sculptural and artistic approach. I use different materials because I think I am looking for unexpected color variation.” She shares, “My designs are different than most Nantucket basket weavers—the styles I have in my head are really exciting, I feel as though I want to translate everything I see into a woven piece.” 

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Joan Peters

In the quaint and quiet village of Osterville, in a small bespoke studio on Main Street, Joan Peters has been meticulously creating unique toile patterns that always enter the design scene as a true original, and more often than not are found to be a strong influence in someone else’s “native” design. This icon of design has not only been creating toile scenes evocative of several popular destinations, but she is actually a board artist, in other words, she draws her designs by hand, without the aid of any mechanical device like a computer program. 

“In the beginning the Cape Cod Toiles really made a splash,” Peters recalls. “French scenes in traditional toiles were always loved and most interior designers used them in countless projects. But I decided the Cape and Islands had scenes and images that in many ways—at least if you were from here or loved coming here—would be meaningful to you if they were in your home.”

As the decades have ticked past, Peters who has also enjoyed  a robust career as an interior designer, has grown her collection of toiles to an even dozen. The destination-influenced designs depict recognizable scenes from Nantucket, Martha’s Vineyard, Boston and now Washington, D.C. 

Peters’ designs, in an array of colors,  have been produced on sumptuous fabrics including cotton and sateens, as well as on rolls of high-quality wall coverings—all produced in the U.S.A. Her designs have been ordered by professionals and homeowners across the country and as far away as Australia. “I don’t know what the connection is for the person in Australia—I would love to know—but it was a big order so it must have some meaning for them,” she shares. 

At a time when women were a rare breed when it came to creating and building a business on their own, Peters found herself a single mother living on Cape Cod. Trained as a graphic artist she knew she had to rely on the talents she had and figure the rest out. “It wasn’t easy, it was a lot of hard work, that sometimes never seemed to end. But I was lucky in that I was able to make a living doing something I truly loved. And I think my designs have always been different and unique, so in that way I have contributed something beautiful to the homes that enjoy my designs,” she reflects.

As her charming and whimsical designs depict, it’s a Joan Peters’ world and we are lucky enough to be living in it. 

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Sandra Moffitt

Sandra Moffitt always knew she was a creative at heart. “I always wanted to be an artist, but you know, I grew up in a time when it was sort of frowned upon. There wasn’t a lot of encouragement that you could make a living while creating art. I am happy to say I proved that idea wrong, and I am also happy that we have now evolved to being able to see just how viable a creative career can be,” she observes.

Even with that confirmation, Moffitt still found herself doing other things in her early twenties until she finally took a surface pattern design class. She says finding this outlet for her creativity opened up a whole world that she felt was just waiting for her to arrive. “I was living in California at the time and it was like a light went off,” she recalls. “I knew then that it was what I wanted to do. For the first time I could see how I could be an artist and make a living.”

Moffitt found work designing for several world-class textile and wallcovering purveyors, yet when she realized her first commissioned order, she knew she had made the right decision. “I spent a lot of time interpreting other people’s designs and freelancing for companies that were producing wallpaper, so in a way, it was a great learning opportunity for me,” she explains. “But when I had the opportunity to make something entirely my own, it was a very different experience. And I am still so proud of that design.” The design she refers to is Singing Beach and the Duxbury resident says it embodies everything she loves about living in New England. 

“The design is all shells. It was very laborious to do, with a huge repeat and is complicated to print. But I just think it turned out really well. It showcases my detailed rendering skills, mastery of printing techniques, and my love of color!” the designer explains, who, like Joan Peters, created the pattern on a board using only her creative mind, pens and paints. Speaking of Joan Peters, Moffit has met her and counts her among the many important influences that has guided her career. “When I first set out to design my wallpaper collection, a colleague mentioned there was someone I should meet on the Cape, and that was Joan,” she recalls. “She is just amazing, the career she has built and the body of work she has created, I can only hope to have some of the same success.”

Moffitt’s designs are available to the trade at the Boston Design Center at Studio 534 and her wallpapers can be viewed at sydneymead.com. 

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Andrew & Megan Nugnes 

Cape Cod natives and former teachers, Andrew and Megan Nugnes, purchased the reputable company HAMCO Flagpoles and Flags in 2020, and have been growing ever since. History, tradition, high-quality products and service are the cornerstones of their business. A member of NIFDA (National Independent Flag Dealers Association), they uphold an oath to represent only dealers, manufacturers, distributors, suppliers and supporters of American-made flags; and additionally, they primarily deal with New England based companies. “The gold ball finials that sit atop the pole are from Connecticut, the line is made in Rhode Island and the fiberglass poles are handcrafted in New Hampshire,” states Megan Nugnes proudly. 

The Nugnes family wants to help you fly your colors in grand style and their unmatched customer service ensures this. A site visit and evaluation, with a subsequent digital rendering for your consideration are all part of the thorough and personal process; the owners adding, “All of our flagpoles have a written guarantee for the lifetime of the pole.” What puts HAMCO in a class of their own and differentiates them from other dealers in the country is a specialized tripod system that securely installs the poles. This endeavor has become a labor of love for the couple and stirred emotions they couldn’t have imagined. Megan remarks, “Clients send us pictures of beautiful sunsets or sunrises and special family events with our poles in the image. We just love what we do.”  Find HAMCO Flagpole and Flags online at hamcoflagpoles.com and see a gallery of their impressive projects or to schedule your consultation.  

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Kristina Manter & Brendan Stearns 

It’s a little bit like a Hallmark movie script how Kristina Manter met Brendan Stearns. The opening scene would be at a popular local watering hole, (The Chatham Squire, natch) where a summer girl, whose jobs were at an embroidery shop and a screen printer, meets a local boy whose design business was just taking off. He asks her to model his latest hat creation and while she agrees, she adds that she can help him expand his business as she has extensive experience in screen printing, embroidery, and sales. A week after that fateful meeting, she had Cape Shark participating in its first pop-up shop and they’ve been leaving their mark on Cape Cod ever since.

Combining his long-time love of sharks with ambition and creativity, Stearns had been learning and growing his business, Cape Shark, by himself until Manter, a helper by nature, enthusiastically jumped in. They discovered a kindred spirit of creativity working alongside each other and growing the business, but it wasn’t just the spark of innovation between them—as any star-crossed Hallmark couple would, the two began dating. 

They signed the lease to open their first store just days before COVID struck, leaving the young entrepreneurs wondering how they would keep their business afloat with the doors closed. Manter recalls, “We ended up cutting up a lot of our inventory and I taught Brendan how to sew and we hand-sewed masks. We donated a lot of them to hospitals, police, and fire departments and we sold some so we could make the rent until we got word from the governor that we could open in July.” 

Today, Cape Shark has expanded by leaps and bounds, with 35 stores that carry their brand and a new brick and mortar shop in Chatham on Main Street. Their apparel is not just trendy but eco-friendly; “We’re the only Cape company to use water-based ink,” Stearns explains, “Most screen printers use plastisol ink, which is essentially PVC (polyvinyl chloride) but our ink has zero plastics which means when our products are in the dryer, they aren’t emitting any plastic, just water vapor.” Concurrently, Manter manages her own brand, Cape Cod Blonde, with a unique line of apparel and accessories. As for upcoming plans, the couple, who thrives off the love and support they receive from their customers, family and friends, are excited for Cape Shark to take an even bigger bite out of the busy season ahead—and oh yes, a September wedding is planned too. Visit them at 1223 Main Street in Chatham, capesharkapparel.com, and capecodblonde.com.  

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Lisa Strock O’Connell 

With a background in biology and botany, Lisa Strock O’Connell certainly has a green thumb. She puts it to work on her North Falmouth micro-farm growing flowers, microgreens and even raising hens for fresh eggs with her daughter, Zoe. 

She has always been an avid gardener, but the entrepreneurship began, perhaps ironically, organically. After O’Connell posted photos of her flowers in painted mason jars, she started receiving requests from friends and neighbors. She continues to use social media, mainly Facebook and Instagram, to communicate the flower truck’s whereabouts and pop-ups.

O’Connell cultivates about an acre of land for perennial and annual flowers and grows all her microgreens in her basement. “The people who are dedicated to coming to Falmouth Farmers Market push me to try to produce and get together as much product as I can. It’s been an amazing supportive community,” O’Connell says. 

She is currently working on force-growing tulips in the basement to have a year-round stock, a testament to her determined spirit. O’Connell also sells “grow your own microgreen” kits. “Everybody can grow microgreens right on your kitchen counter, and its especially fun for kids,” she says. Microgreens are able to grow in just two weeks, a great green project for impatient young gardeners!

You can find Lisa and the Cape Cod Flower Truck on Instagram @capecodflowertruck.  

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Briana Silvio 

After resigning from her corporate job in February 2020 and the onset of the pandemic in March, Briana Silvio found herself in a scary, isolating position. Searching for a way to both find financial security and reintroduce joy in her community amidst a pandemic, Silvio considered balloons. 

“I saw the need in the community for people to feel happy,” she says. Silvio decided to fill large gift bags with balloons and deliver them to friends’ doorsteps. Soon after, people reached out to buy the Bags of Sunshine, as she coined the surprises. “It just kind of like went off like wildfire,” Silvio recalls.

Now, Silvio serves corporate clients and the event industry across Cape Cod and into the Boston area. Capitalizing on the robust wedding industry, Silvio is able to bring creative balloon installations to many celebrations. Elevated Impressions also offers rentals like large, light-up marquee letters. 

Despite its growth, the business’s mission remains the same from the outset: to encourage people to celebrate life. “The community is always going to be the driving force,” Silvio says. With the community in mind, Elevated Impressions only uses 100% biodegradable balloons and never lets an inflated balloon leave the studio without a string and weight to avoid any fly-aways. 

Silvio is excited to look ahead at more business opportunities. Elevated Impressions already has the most summer bookings in the business’s history and Silvio is headed to teach a class at a major balloon manufacturer’s convention in June. 

Inquire for an event at elevatedimpressions.com. 

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Seth & Megan Burdick 

For those who have had the opportunity to meet Seth and Megan Burdick, even just once, the couple’s lasting impression of their enthusiastic embrace for their community is a take-away as nourishing as the myriad of products they sell in their markets. The Burdicks who purchased the beloved Cotuit Fresh Market in 2019, have established their place in the heart of their community through their dedication and hard work in a very old-fashioned business of providing sustenance for their customers. Cotuit Fresh Market is one of those throw-back establishments, where the wooden floors all slant a bit, creak with an accumulated history of generations of patrons and every bit of space is occupied by products and homemade products that harken from another time. 

“It’s not just us,” Megan affirms with her indelible smile. “Our team is as invested in the business as we are. Every single person strives to make sure the customers have what they need and are satisfied with what we offer.” Megan’s observation is confirmed by the ever-present line of hungry patrons at the daily counter, morning-to-night. The take-away entrees and sides fill a refrigerated case ready to make a busy day—whether due to a full slate of beach activities, or a long commute from off-Cape—end on a delicious high note.

In April of 2024, the Burdicks have expanded their business of caring for their community as they opened their new location, Mashpee Fresh Market in the heart of Mashpee Commons. This new store is brighter, and slicker, yet still exudes the caring and thoughtful vibe the Burdicks bring to everything they do. Seth says, he always knew there was a second location in their future. “Well, I didn’t know where or exactly how, I just knew we could do it,” he explains. “We opened a summer market at the Popponesset Marketplace and although it was smaller, it still required every aspect of opening a new store. That store was so successful, I knew we could do it here in Mashpee, it just became a matter of scale.”

The thoughtful curation at the Mashpee Fresh Market is immediately evident in the quality and unique nature of the products and the way in which they are displayed. The store is clearly born of a different century than it’s Cotuit ancestor, and the vibe is a bit different as well with a bustling crowd fresh out of the bespoke shops, yet the genetic make-up is undeniable: the Burdick’s have applied their unique mix of attentive consideration and commitment to the shopping experience of every customer that comes through the door. The staff once again is friendly and helpful and usually either Seth or Megan are checking in personally with the customers to gauge their reaction as well as their feedback.

“Every product in this store was a conscious decision, and not without a fair amount of research,” Megan adds. “And we have given a lot of consideration to the shelves and end displays so things don’t get lost or overlooked.” In addition to the note-worthy products and brands Mashpee Fresh Market offers, the freshly made sandwiches, salads and take-away items they have become known for in Cotuit are all in attendance and very much in demand. 

In an effort to create a neighborhood hub—a destination as in simpler times where people gather, connect and re-stock, the Burdicks have reproduced their recipe for a good-old-fashioned mercantile that feeds the body, mind and soul of their neighbors.  

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Gabriel Beaton 

By definition, an entrepreneur takes greater than normal risk, and certainly opening an art gallery on Cape Cod in December of 2021 would be considered risky, but Artnova Gallery owner Gabriel Beaton was undaunted. Through unfortunate circumstances, the previous gallery that occupied the space was slated to close so Beaton decided to take a leap of faith. He says, “I knew that if I had the mind to do it, now would be the time.”

He scraped together what he needed to secure the location and began to put together a list of artists he admired and whose work he already knew. “December was our first month of business,” he recalls, “which is unusual as most places will close or use the colder months to prepare for the summer. It just happened that the timing was unusual, but I decided to open even though I hadn’t even fully fleshed out the entire concept yet. Looking back, I see that it was kind of perfect. It gave me that down time to prepare.” The vibrant Main Street of Chatham that you find in the Cape’s busy season is contrary to what you will find in the dismal months of January, February or March, but Beaton maximized the desolate time to redo the floors, paint and construct new walls and create display space. The true grand opening at Artnova took place on Memorial Day and Beaton has been living the dream since.

Perhaps the spark that lit his entrepreneurial spirit was ignited as far back as his first job in high school where he worked at a small, local coffee shop owned by a young couple who were bringing their dream to life in his hometown of Portland, Maine. He muses, “After working there a few months they made me the assistant manager. They ran their business successfully and I watched how they did it. The single, biggest, most important thing was that I felt so honored that they trusted me—I was determined to do a good job for them. Since then I’ve thankfully had a handful of people in my life who have shown me that all this is possible—that I can make a dream into reality by just putting one foot in front of the other.” 

Beaton’s path to success has been anything but linear, weaving in and out of a variety of creative roles over the years; but he acknowledges that this is ultimately his recipe for success and the environment in which he thrives, ruminating, “It’s said that if you aren’t building your dream, you’re building somebody else’s.” 

Beaton’s authenticity and passion for what he does exudes from him and occupies every facet of how he operates Artnova Gallery. “Whatever iteration of this entrepreneurial path that I’ve been on, the constant for me is that I feel so authentic and genuinely passionate about what I’m doing. There’s nothing more personal to me than getting to show the world the artwork that is created by my family and friends. I think if someone is considering going out on their own that would be my advice—just make sure whatever you are doing gives you those butterfly feelings.”  

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Donna Devine 

Originally from the Cape, Donna Devine ventured away due to high living costs, spending years in Cincinnati and Boston before returning home. Her move back was fueled by a simple question posed by a magnet on her corporate desk: “What would you attempt to do if you knew you could not fail?” Her answer? To afford to move back to the Cape, not just to return, but to thrive.

Back on the Cape, Devine made moves to secure the future she desired. After responding to a Facebook advertisement selling a Magic Mirror photobooth, Devine became the proud owner of her new business, Magic Mirror Cape Cod. Magic Mirror provides photo booths for corporate clients, weddings and private events. It is also debuting a new model, drop-off booths, which tend to be much more affordable.

Utilizing the Entrepreneurship for All Business Accelerator program, Devine grew both her business capacities and professional network. She received two program grants which enabled Devine to purchase her second and third photo booths. At the same time, met with multiple town officials and event coordinators, which developed her relationships and got her name into the community.

Today, Magic Mirror is involved in many community-oriented events, like the Barnstable League of Women Voters. “I also work with a lot of nonprofits and offer them a discount. That’s really elevated my business,” Devine says.

She is proud of what she has accomplished and grateful for the support she has received. Devine is thrilled to be back home on the Cape, where she is living her dream and making a difference in her community.

You can contact Magic Mirror at 844-678-9846, magicmirrorcapecod.com,  or on Instagram @magicmirrorcapecod.  

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Jessica Georges

Jessica Georges might not be a Cape native, but she has embraced the lifestyle with exceeding vigor. Captivated by the Cape’s environment and natural beauty, Georges was inspired to create Green Road Refill, a low and zero waste store stocked with over 40 varieties of natural soaps, detergents, cleaners and more! 

Georges found support for her business in the Entrepreneurship for All program, a training and business accelerator program open to any applicant. Green Road Refill began as the Sally Sud Shed, a mobile low-waste refill shop that Georges toted around the Cape to farmers markets and community events. “There’s a lot of people that choose to live on the Cape because of the bounty in nature. People value the environment and want to support it,” Georges says. Finding success and support in the community, Georges debuted the Brewster brick-and-mortar location in 2021, exhibiting her commitment to making conscious consumption attainable for locals. 

While the mobility of Sally Sud Shed is largely limited to the seasonal months, Georges is excited to begin partnering with other local businesses and set up permanent pop-ups across the Cape where customers can refill their sustainable products. Additionally, Georges has partnered with her friend Tarraza Millard to provide beautiful refillable soy candles in store.

Georges is clear—the community has made Green Road Refill a success. The like-minded, eco-conscious Cape Codders and supportive small business owners have allowed the refill store to open, expand and ignite a more environmental Cape. 

You can visit Green Road Refill at 2655 Main St, Brewster, MA 02631 where you’ll find over 10 local makers in the shop, with offerings that range from jewelry to bath and body and self-care. Find the Sally Sud Shed on Instagram @greenroadrefill or their website greenroadrefill.com.  

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Erika & Peter Orlandella 

Since it was first purchased and dubbed Cape Cod Winery in 2013, by Erika and Peter Orlandella, the iconic spot in East Falmouth has grown to become a staple for locals and a box to check on many visitors’ bucket lists. 

“The community really picked up on what we were trying to do,” shares the duo. “They allow us to think ‘outside of the wine box.’” Focusing not only on good quality wine, they wanted to concentrate on the experience itself as a whole. “We want people to come to the winery and leave feeling great,” Erika says. “Putting people in a good mood is really our entire concept.” Featuring large farmhouse tables, shaded areas, live music, local bites, and a fun family-friendly atmosphere, the winery is truly the quintessential hangout spot. 

Last summer they even opened their own food truck to add more consistency and variety in their food offerings named the Mermaid Kitchen—a nod to their iconic mermaid logo. “We kind of really ran with the mermaid thing,” laughs Erika. “Because our Mermaid Water Rosé is really what put us on the map.” 

So what’s next for Cape Cod Winery? In 2024, they’re partnering with even more local talent. “We’re going to start hosting comedy shows, farm to table wine pairings in partnership with local chefs, sip and paints, even country line dancing and a murder mystery night this summer!” enthuses Erika. “You can still come in and enjoy a glass of wine, but now you’ll also be able to buy tickets for even bigger events, most of which, just like our annual tree lighting, benefit local nonprofit Tommy’s Place.”

A family business through and through, for the Orlandellas, their winery is all about the community coming in and enjoying the company of their friends and family. They note, “We wouldn’t be able to do it if the community didn’t come out and support it.”

Located at 4 Oxbow Road in East Falmouth. Learn more at capecodwinery.com.  

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Sarah & Taylor Powell 

What happens when two entrepreneurs meet and fall in love while following their dreams on the Cape? They combine their passions to create a welcoming spot for Cape Codders and visitors alike to “Drink Like a Local.”

Taylor Powell initially opened Perks Coffee Shop in 2010. “That was before me,” smiles Sarah Powell. In 2012, there was more than just good coffee brewing at Perks, as they both found themselves working and falling in love in Harwich Port. “Back then, there wasn’t much happening in Harwich,” laughs Sarah. With a liquor license for beer and wine, and Taylor’s idea of incorporating live music, the duo organically started to grow their business into Perks Coffee Shop & Beer Garden. “My uncle helped us build the back bar, we built the stage, and then we realized we could get a seasonal full liquor license. I think it was always Taylor’s dream in the back of his mind, but together we were able to create that fun environment and fill a need for the town.”

Along with coffee, beer and spirits, Perks offers elevated bar food. “My husband designed the menu off of what he loves and all of the dishes on the menu he created.” And the iconic “merch” you may see people rocking, “That’s all me!” shines Sarah. With her background in fashion, Sarah was excited to collaborate with local artist Peter James Glen who also did all of the artwork inside the front bar and along the wall outback. Together, they created the Perks logo and “just ran with it.” She shares, “We’ve done really well with it, my friends are always texting me saying they had a Perks hoodie sighting—nothing feels better.”

For the Powells, Perks is more than just a business, “We’re both there 24/7,” confirms Sarah. “We have people that are there in the morning getting coffee, I’ll see them again in the afternoon and then at night having a beer. It has that warm, welcoming ‘good vibes’ family environment. I think when people come to Perks they feel good, they feel at home—plus we have really good coffee,” laughs Sarah, “and a really good alcohol selection—it’s a pretty cool spot and it is something that we created together, the two of us, without any outside help. We love it so much and I think people feel that love.”

Located at 545 MA-28 in Harwich Port. To learn more, visit perkscapecod.com.  

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Kevin Bennett 

For a young boy growing up on Cape Cod and loving everything this special landscape has to offer, the choice of where and how to build a life as an adult can be more challenging than it should be. The challenges for young adults to build a life that is both fulfilling and financially rewarding on the Cape have become all too commonly discussed, and the successes all too rarely realized. 

Kevin Bennett grew up on the Cape, the son of educators in the Barnstable school system; his mother a sixth-grade teacher and his father a high school history teacher. His idyllic childhood was the stuff of a seaside Huck Finn, “I have always loved the outdoors,” Bennett affirms. “I think that is definitely directly related to growing up here.” Bennett’s love for the landscape of the Cape found a natural outlet through his innate gift for photography. With a degree in visual arts, Bennett says he had no idea what he was going to do after college. Longing for a thriving environment where he could still indulge his love of the outdoors, Bennett moved to San Diego where for six years he was a second-grade teacher’s assistant, whose duties included teaching art classes, at a private secondary school. Of course, life has a habit of intervening, and a call from Bennett’s family with news of an unfortunate diagnosis for his father, found the newly 30-year-old assessing whether he was a long-time West Coast or East Coast guy.

A return to the Cape prompted a successful recovery for Bennett’s father—who along with his wife run a comfortable bed-and-breakfast in Hyannis after retiring from the school system—and found Bennett  in a stint substitute teaching in the Barnstable schools and participation in the summer HyArts Artist Shanties to showcase and sell his photography. “I did pretty well, and I found that I ultimately enjoyed it,” Bennett says of the creative endeavor that ultimately led to the fortuitous decision for Bennett to open Bennett Gallery and Framing on Main Street in Hyannis in 2017.

Focused on being a good neighbor and Cape Cod collaborator, Bennett made it a point to introduce himself to the other gallery and frame shop entrepreneurs across the Cape. One of those individuals, Amy Rice who owned Woodruff’s Art Center in Mashpee, became a good friend and valuable professional ally Bennett says. “When we first met she asked if I was interested in some framing equipment she had, and I was. We hit it off pretty quickly and would always be in touch. I would frame things that were out of her scope and she, of course, was so generous in her business advice, since she had been doing it so long.” 

In the summer of 2022, Woodruff stopped into Bennett’s Hyannis gallery to pick-up a piece he had framed for one of her customers. “I asked her how she was and she said, ‘Tired, I’m ready to do some traveling and stop working.’ I told her when she was ready to sell her gallery, give me a call. She said she gave her broker my number the day before,” Bennett recalls with a smile. Bennett acquired the Mashpee gallery in the fall of ’22 and things really began to take off. His Hyannis gallery showcased his photography and a small handful of other local artists’ work. In Mashpee, he inherited an established group of popular and thriving artists whose work was either benefitting from a demonstrated following or enjoying a new introduction into one of the more robust artist collectives on the Upper Cape. And he now has employees to manage. “The management of people was one of the new things I had to learn,” Bennett shares as he has observed that empowering instead of overpowering seems to be an effective approach for his team. 

A year after acquiring Woodruff’s, Bennett heard from the broker again, this time to let him know the venerable art gallery in Orleans, Tree’s Place Gallery was now up for sale. The property also included the valuable Cape Cod Photo, Art & Framing business, which also appealed to Bennett’s business plan. The artists represented by Tree’s have vaulted Bennett as a gallery owner and entrepreneur into a completely different stratosphere, allowing this young man who embraced his youth on the Cape to build a future in the place he is able to call home.