“I was always climbing a tree. Always.”
For Jason Wilcox, the fascination with trees goes back to his earliest memories growing up in Ivoryton. The way they branched out. Their resilience in the changing seasons. How each had a unique character. That they were all so beautiful and so much a part of the landscapes he loved.
During his high school years, Jason decided a good way to make some summer cash was to take care of some trees. He was by no means an arborist yet – heck, he was not even an adult yet – but Jason Wilcox thought he had found his calling. Still not completely sure he could turn the summer job into a career, Jason studied marketing in college, only to confirm “that definitely wasn't what I wanted to do. I wanted to get back outside.”
So, by the next summer, he was resolute on his plan. The year was 1984, and Wilcox Tree Experts was born.


Jason Wilcox is a humble man – to the point that, when asked about the now-lengthy history of his business, Jason simply says, "I started with a pickup truck, and just one thing led to another, and slowly grew to where we are now."
As he finishes his highly-summarized chronology of the company, Jason emphasizes that Wilcox Tree Experts has taken itself to the next level since his son, Hunter, and daughter, Jessi, joined the team.
Hunter came on board in 2022. While at the University of New Hampshire – where he earned a degree in Outdoor Education and Business Management – Hunter explored his own entrepreneurial spirit by running a water taxi on Block Island. Once he was out of college, Hunter expanded his business interest and built a successful sailing charter in Saint Thomas, one of the U.S. Virgin Islands in the Caribbean Sea.
“I learned so much about running a business through that experience,” says Hunter, “but the whole time I had this thing in the back of my mind, that my family's business back here in Connecticut was so well established and had such a great reputation. It felt like something worth continuing.”
Jessi leads the office operations of the company, taking over for her mother in the role which includes everything from bookkeeping to marketing. “ I never thought I would have any part in the business growing up,” Jessi admits, “just because I didn't see myself being an arborist. But observing my dad and getting the inside scoop of the business was interesting to me.” So, while working for a nonprofit organization in Utah, Jessi decided it was time to explore officially joining the family business.
As a younger generation with business acumen is apt to do, Hunter and Jessi have introduced a more technology-driven approach to running Wilcox Tree Experts.
“When we got involved, [Jessi and I] helped with various things technology-related,” says Hunter. “Some of the implementations that brought the company up to the digital age really came down to organization. Now we have the ability to take on more responsibility.”
The technology and logistical streamlining allows the Wilcox crew to service a sizable footprint from their Old Lyme headquarters – out towards Stonington, up towards East Haddam, over to Branford, and everywhere in between.
“My dad has always been the guy holding it all together,” Hunter remarks, “and I think him being able to rely on my sister and me as people who are dependable and invested has been a dream come true.”


Many people are shocked to hear what goes into a full-service vegetation management business. "It is certainly not," as Jason describes, "a couple of guys with chainsaws," and it requires immense resources – both strategic and financial – to handle the daily pressures.
Jason and Hunter are both licensed Connecticut arborists. To earn a license, individuals must apply to the Department of Energy and Environmental Protection (DEEP) and pass a notoriously difficult process that involves a written test, tree identification exam, and 10-question practical. Preparing for the series of tests usually involves an equally rigorous, multi-month course.
Beyond the expertise and practical experience, tree service businesses also need sophisticated equipment. “We’re constantly updating and keeping everything state-of-the-art,” says Jason, “making it a safe situation for employees and customers.”
In the last few years alone, Wilcox Tree Experts have amassed several million dollars worth of equipment – aerial lifts, cranes, chippers, mini loaders, and a fleet of trucks. “T he amount of capital investment that is required to keep up with the business is substantial,” says Hunter, “so having a good relationship with a reputable bank that can provide quality service is really important.”
Enter the team at Essex Bank.

"I have been with Essex Bank," Jason tries to recall, "since around 1985." In fact, he says, Wilcox Tree Experts became the first commercial loan of now-retired CEO Diane Arnold when she was a young lending officer.
“The aspect I like most about Essex Bank is that they recognize who we are, so they understand how to lend money when we would like to make a move. They always have very competitive rates, and they are family people like us.”
As an operations manager, Jessi appreciates the access she gets to the technologies and teams of the Bank. “ Working along with Essex Bank has been really great. They are always very quick to respond, help out with a question I might have, or if I'm dropping off a deposit at the bank. I see these people on a weekly basis, and that relationship of knowing who you're talking to, and them being there to answer any questions, has been really helpful for me in my role.”
"We use a lot of their online banking to keep track of different loans – what's due, when it's due, and it's an easy way to have everything in one place. They make it very simple."
Jessi Wilcox

Clear Understanding
Jason enjoys the genuine connection between Essex and Wilcox Tree Experts. “The Bank is always there if we need them. When we have a conversation, they know who I am and what I’m talking about. I’m not just a number.”

Accessible People
Jessi relies on the availability and insights of the Essex Bank team. “You can call and actually talk to someone on the phone. You don’t have to click through a bunch of numbers to try to get a hold of an actual person.”

A Stable Relationship
Hunter appreciates that the Bank behaves like a true partner. “There’s a certain level of security that we feel dealing with a bank that knows us. They’ve seen our company grow, and they recognize our needs.”
When asked about the ideal customer, Jason replies in his jovial and understated manner, “I mean, they’re all good.”
Jessi references this genuine point of view as more than just a casual comment. “That’s something I really appreciate about both my dad and my mom. They see the value in the people that are working with them.”
Jason goes further, likening his view of the customer relationship to the reason he enjoys working with Essex Bank. “I think a preferred customer is one that recognizes and appreciates who we are, and that we stand behind what we do.”

Like he has for thousands of mornings since 1984, Jason Wilcox still gets up each day with a smile on his face. He never tires of tending to the tree-lined landscapes throughout the Shoreline and River Valley.
When he heads out for the day, Jason takes the front door, just beyond the open plan living room and kitchen of his home. Above the sink area, there is a large framed print. One might think that spot would be reserved for a family photo (of which there are dozens proudly displayed throughout the house), but in the Wilcox homestead, there can only be one thing – a majestic black and white image of a tree.


With Hunter and Jessi firmly in the family business, Wilcox Tree Experts is proud of its legacy and poised for more success.
“This all started with just my dad,” says Jessi. “Then he had one other guy working with him. Then two. Now, we have three different crews working on any given day. So, the business has grown a lot.”
Growth often leads to quite a bit of change, but what maintains is the family’s work ethic, as well as the respect they have for one another. And, based on his wide-eyed wonder when seeing the equipment, maybe Jessi's baby son, Archie, is a future generation of the business.
“We’re all there to help each other out, even if something might not be part of the job description,” says Jessi. She adds, “and working with my dad, I’ve gotten to see that relationships are a really important part of the business.” Says Hunter, “I always recognized my father as someone who would go the extra mile, and was willing to put in the extra work to provide for his family. I want to do the same.”
Jason adds a final comment – succinct but meaningful.
"Wilcox Tree Experts is kind of a family thing, and we love it."

Essex Bank Products & Services Used By Wilcox Tree Experts
More Information About Wilcox Tree Experts
61 Buttonball Road
Old Lyme, CT 06371
860.434.2103