Cheney Financial Group Makes Transition to Next Generation

Three Damariscotta businesses are being passed down to a new generation.

After working at the Cheney Financial Group for over 40 years, Dennis Hilton is making way for his children to lead Newcastle Realty, Cheney Insurance, and Newcastle Vacation Rentals.

The businesses’ new ownership group includes Hilton’s sons Nathan and Chris; daughters-in-law Hannah and Jessica; and longtime employee Joe Ford.

Ralph Cheney and his son-in-law Mac MacKechnie opened Cheney Insurance in 1954. Dennis Hilton’s father, John Hilton, started working at the agency in 1968. As he continued working, John Hilton became the “heir apparent” to the insurance agency, according to a 1998 article from The Lincoln County News archives.

Even though MacKechnie and John Hilton weren’t related, Dennis Hilton said in the 1998 article that the Cheneys and MacKechnies “were part of our family” as the Hiltons took over Cheney Insurance and helped take care of MacKechnie’s
parents.

Dennis Hilton jumped into the family insurance business after graduating high school, helping usher Cheney Insurance into the
computer age during the 1980s. He worked as an insurance agent before quickly climbing the ranks and taking over the insurance agency as well as the realty business.

Over the course of 40 years, Hilton said one of his biggest accomplishments was fostering Cheney Insurance and Newcastle
Realty’s expansion through acquisitions.

“Cheney Realty Co. was one of the smallest real estate companies in the area,” Hilton said. “We bought what was then the largest in our town, and we merged them together … to (create) Newcastle Realty.”

After the acquisition of Newcastle Square Realty, Hilton also built up the existing vacation rental operations into a new venture,
Newcastle Vacation Rentals, in 1998.

As the owner of a multigenerational business, Hilton said he always hoped his kids would take on the three operations.

“I think that’s any parent and business owner’s dream; to have their kids want to take over what the parent has spent their lifetime cultivating and nurturing,” he said.

Over the years, he had accepted the possibility of selling to outside parties, which he said made his sons’ eventual interest in taking over all the more exciting. Chris Hilton said he remembers roaming the halls of Cheney Insurance, then located in the
Damariscotta storefront that is now Newcastle Realty, while he was a kid, watching his grandparents and then his father run operations.

With the extensive family history and the strong operations at all three companies, Nathan Hilton said he and his brother didn’t want to pass up the opportunity to take on the Cheney Financial Group and continue his dad’s work.

“We felt like we wanted … to continue the legacy that the companies have had in the community all these years,” Nathan
Hilton said.

As his sons also manage their own landscaping business, Dennis Hilton said Chief Operating Officer Hannah Hilton and Chief Financial Officer Ford have been “critical components” during the ongoing transition.

Hannah Hilton joined Cheney Insurance as an administrative assistant five years ago. Like her father-in-law, she quickly moved up in the company to her current role.

“Hannah’s the one that took the initiative,” Dennis Hilton said. “She really had a thirst for knowledge.”

As she takes on more of a leading role and manages day-to-day operations, Hannah Hilton said she takes the responsibility of
maintaining the service customers expect seriously.

“We have come to be that reliable, steadfast family-owned business,” Hannah Hilton said. “I want to stay true to what people
here in our community have come to rely on while also continuing to modernize.”

In his role as CFO, Ford said he was brought on to the ownership group to give an “impartial, outside financial focus” to the collective. As he helps the next generation of Hiltons implement their goals, he said he’s focused on aiding intentional growth.

“We’re a fixture in the community,” Ford said. “I think we’re in a good position to grow, and I’m behind the next generation
for that.”

The transition started 18 months ago and remains underway, allowing for a gradual change across the three companies. Dennis Hilton remains a key part of administrative operations even as he prepares to eventually retire.

“We’ve been doing things behind the scenes to get the family more involved,” Hilton said. “It doesn’t just happen overnight; it needs to be a careful, coordinated, planned process.”

Jessica Hilton said in an email both Dennis Hilton and Hannah Hilton have been instrumental to the successful transition, helping to “guide the rest of us as we learn” and start to determine their respective roles.

At present, Hannah Hilton has taken on management of the insurance and rental divisions while Dennis Hilton continues to
lead Newcastle Realty.

“I’m just so proud that my kids are going to make a fifth generation out of this story,” Dennis Hilton said.

It’s been exciting to learn the ins and outs of the family company, Nathan Hilton said, and he looks forward to preserving the traditions and core values associated with the Cheney Financial Group.

“I believe our grandparents would be proud to know these businesses will remain in the family, locally owned and rooted in the community for another generation,” he said.

The Cheney Insurance and Newcastle Vacation Rentals offices are located at 277 Main St. in Damariscotta, and Newcastle
Realty’s offices are at 87 Main St. in Damariscotta and 14 Todd Ave. in Boothbay Harbor.

For more information on Cheney Insurance, call 563-3435 or go to cheneyinsurance.com.

To learn more about Newcastle Realty, go to mynewcastle.com or call 563-1003 to reach the Damariscotta office or 633-4433 to
reach the Boothbay Harbor office.

For more information about Newcastle Vacation Rentals, go to mainecoastcottages.com or call 563-6500.