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Three iconic Chatham businesses have passed the torch to a younger generation who vow to carry traditions forward.

New Chatham Squire owner Todd Hearle (center) is pictured with his parents, Ron and Debbie, and his five kids (left to right): John, Reed, Alexa, Dalton and Hudson.
“The Flagship of Chatham,” oil on canvas, by Debbie Hearle
Keeping the Magic Alive

Chatham Squire

When contemplating the next chapter of their iconic Main Street restaurant and tavern, Richard Costello and George Payne, who established Chatham Squire in 1968 and last June celebrated its 50th anniversary, wanted to ensure that its next owner would safeguard the culture of the legendary establishment. Enter investment banker Todd Hearle, who moved to Chatham with his family at age 12, and for whom The Squire holds many fond memories.

“Richard and George were legends to me as a kid,” says Hearle. “My parents own The Hearle Gallery across the street, and when a painting sold, the big treat was to get burgers and fries at the Squire.” Although Todd went away to attend boarding school, college and then to pursue a career in investments, his home base remained in Chatham, where his parents, Debbie and Ron, have lived year-round since 1984. These days, Todd and his five children (ages 5 to 18), split their time between Connecticut and Chatham—with the idea of gradually transitioning toward Chatham. “At the end of the day, it’s where I want to be full time,” says Hearle.

Negotiations for the sale of the Squire began quietly several years ago. Costello and Payne took the time necessary to ensure they found the right person to carry on their legacy. “We feel good about Todd,” says Payne. “He grew up here in Chatham, he’s a family man and he loves the Squire.” Hearle credits Costello and Payne for their careful deliberations and for demonstrating what he describes as intellectual honesty. “I’ve always been convinced in my heart of hearts that the Squire was a truly special place with deep community ties, trust and kindness,” adds Hearle. “I wanted to be part of that, ensuring the legacy of Richard and George.”

As the first pages turn in this new chapter of Squire lore, Hearle reflects on comments people make when they hear that he purchased the business. “Everyone’s asking, ‘What are you going to do?’ and I tell them ‘The Squire is The Squire—it’s like hallowed ground to me,’” Hearle explains. “It’s a je ne sais quoi; you can’t put your finger on what the magic is, but it’s there.” Hearle plans to keep it running much like it has, entrusting the staff, many of whom have worked there for decades, to do what they do best. “This organization has been honed for many years,” says Hearle. “Everybody does their job, just like Belichick—and they do a really fantastic job.”  Chatham Squire, 487 Main St.,, 508-945-0945

Young married couple Robbie Carroll and Paige Piper are the new owners of the Chatham Candy Manor.
Finding Their Sweet Spot

Chatham Candy Manor

While keeping 60-plus years of traditions intact at the iconic and beloved Chatham Candy Manor, new owners and married couple Robbie Carroll and Paige Piper—both graduates of Bentley University—hope to make their own mark on the business, establishing new traditions and broadening its online presence. With the sun setting on their first full summer season at the helm, the entrepreneurial couple is eager to apply their business and marketing expertise to satisfy sweet-toothed patrons both near and far during all the seasons to come. While the shop remains open year-round (closed only on Christmas), seasonal visitors can also get their Candy Manor fix through their recently updated online store. “We really want to communicate with our customers in new ways—not just in the summer, but year-round via the internet,” says Carroll.

When longtime patrons hear the news of the change of ownership, some express concern. “You see the panic in people’s eyes,” says Carroll, “and they say things like, ‘Nothing’s changing, right?’” The couple is quick to allay those fears, assuring customers that Candy Manor’s unique recipes, quality products and customer service will remain as exceptional as ever, as will the staff, most of whom have been with the business for 10 years or more. “We can’t say enough about the staff here,” adds Paige. “They are so integral to Candy Manor’s success in the past and also moving forward.”

Robbie’s respect and nostalgic appreciation of Candy Manor comes from his long association with the much-revered shop. “My mom has worked here for about 40 years, so I grew up sneaking into the back of the Candy Manor at night as a kid,” says Carroll, with a laugh. “Later, when I was in high school and college, I worked here making fudge—it was great.” Piper, while having grown up in Maine, quickly developed an appreciation for the special place that Candy Manor holds in the local community and beyond. “Candy Manor is so established and has such a rich culture,” says Piper. “Being able to be a part of it and also add our touch to it is really cool.”

With the holiday season fast approaching, Carroll and Piper plan to continue long-established traditions at the shop, such as the candy cane-making demonstrations. “People love seeing the whole process of making them right in the shop, with the little song that goes along with it,” says Piper. The couple has also introduced a Candy Manor Advent Calendar, featuring a select hand-dipped chocolate for each day of December leading up to Christmas. “It’s so much fun,” Robbie says with a smile. “It’s something very special and unique.” A sweet spot indeed.

Chatham Candy Manor, 484 Main St.,, 508-945-0825

Yankee Ingenuity founding owner Jon Vaughan and his wife, Sharon Hayes, recently handed over the reins to their niece and longtime employee, Michelle Millett.
An Ingenious Yankee Swap

Yankee Ingenuity

Gift-givers in Chatham need not worry about the transition taking place at Yankee Ingenuity, as founding owner Jon Vaughan and his wife, Sharon Hayes, pass the reins to their niece and longtime employee, Michelle Millett. Vaughan was just 26 years old when he started the business more than 48 years ago, originally focusing on antique restoration and sales. Gradually morphing into the renowned gallery and gift Mecca it is today, Yankee Ingenuity has delighted generations of locals and visitors alike with its eclectic array of unique items, from the whimsical to the ingeniously practical.

Reflecting on the transition of ownership, Hayes, who has worked at Yankee Ingenuity for more than 33 years, explains that the process started well over a year ago. “Michelle has been employed with us for 15 years, and she’s been the manager for 12 of those years, so it was time to do something more formal.” Michelle remembers visiting the store as a child when her aunt came to do the bookkeeping. “I would come in with Sharon after school, and I was just fascinated,” reminisces Millett. “I just remember it being such a magical shop—I never imagined I would work in it one day, much less become an owner of it.”

Asked if the transfer of ownership will usher in any substantial changes at the iconic shop, Millett says, “Nothing’s really changing at all. I have a passion for gift-giving, so I get so happy when I can help someone pick out a nice gift for a good price. For that, we rely on Jon’s rule of thumb for shopping.” Vaughan laughs as he explains his “Ooh, Aah” method for choosing Yankee Ingenuity’s surprisingly affordable merchandise, a method they all swear by: “At trade shows, when an interesting item catches my eye, I say ‘Ooh,’ and then, if it is reasonably priced, ‘Aah.’ If the price is too high, I mutter ‘Oh’ and move on.”

While Michelle provides continuity for customers and staff as she oversees the bulk of the day-to-day operations, Vaughan and Hayes revel in having more time to spend together to enjoy the Cape, as well as pursue their individual interests—his in photography and hers in painting. With the shop soon celebrating its 50th anniversary, Vaughan plans to publish his second book of photography in time to coincide with the milestone. As for the future, Vaughan says, “People should expect a change: They should just expect it to get better,” to which Hayes adds, “It’s going to be great.”

Yankee Ingenuity, 525 Main St.,, 508-945-1288

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