Iconic Chatham Squire To Be Sold

By: Tim Wood

Topics: Business

The iconic Chatham Squire restaurant and tavern on Main Street is being sold to only its second owner in a half century. TIM WOOD PHOTO

CHATHAM – Perhaps the town's most iconic restaurant, The Chatham Squire, is being sold.

Richard Costello and George Payne, who started the Main Street restaurant and tavern in 1968, are selling the business and real estate to Todd Hearle, a Connecticut businessman who grew up in Chatham.

General Manager Richard Sullivan confirmed the sale Tuesday, stating that it is expected to be completed by Memorial Day. The sale includes both the business and the 489 Main St. property, he said.

“Nothing's changing,” Sullivan said. “Everything is business as usual. Nobody's losing their job.” Staff members were informed of the pending sale Saturday. Sullivan said he will continue as general manager and Bob Davis is staying on as executive chef.

“At this point it runs like clockwork because so many of us have been here for so long,” Sullivan said. “Everybody feels positive and comfortable” about the transition.

“I feel like I've spent my entire career trying to find my way back to Chatham,” Hearle, 46, a credit investor who lives in New Canaan, Conn., said in a telephone interview Tuesday. “When this became an opportunity it really piqued my interest.”

Hearle moved to Chatham with his family, parents Debbie and Ron and brother Michael, when he was 12 years old. He went to junior high school here before attending boarding school and college and launching a career in finance. He and his wife Mia have five children ranging in age from 18 to 5.

Known for its two distinctive sections—the restaurant on the west side and the tavern on the east—The Squire is both a popular dining location for locals and tourists as well as a night spot frequented by a range of patrons from fishermen to college students. The tavern's décor features distinctive license plates from around the country. “No license plates are coming off the wall,” Sullivan commented.

Rumors of the sale of The Squire have been swirling for years. “This one seemed to click with the guys,” said Sullivan. “It had to be the right people, people that understand the fabric of Chatham, what The Squire means.”

Hearle's mother, Debbie, is an artist who operates the Hearle Gallery located across Main Street from The Squire. He visits his family regularly and often stops at The Squire.

“It's one of those spots you want to touch base with when you're in town,” Hearle said. “When you walk in, you feel that it's the nucleus of the community. You don't find that too often these days.”

He said he was looking to take a break from his career and searching for a “special business” to buy.

“The plan is to keep it the same, to preserve the legacy Richard and George created, and to keep the team as a cohesive unit and try to do our best to perpetuate the magic that everyone seems to feel about the place,” he said, adding that he hopes to eventually move to Chatham fulltime.

While The Squire itself is certainly iconic, so too are its founders. Costello and Payne were hands-on owners for many of the restaurant's years, but “50 years-plus is enough,” said Costello, a former selectman. The restaurant brought many people to town and contributed to the community, he said.

“The good parts outweigh the bad,” he commented, adding that he's “looking forward to getting to know the Bahamas,” though he will remain a Chatham resident.

“They've had an awesome run,” Sullivan said of the founders, who he expects to continue to drop by from time to time. “They'll still be poking around,” he said.

According to the liquor license transfer application filed Tuesday, Hearle is the manager and sole owner of OneDrop Holdings LLC, owner of OneDrop Operating LLC, which is purchasing the business, and OneDrop Real Estate LLC, which is buying the real estate. the entity purchasing the business. The financial disclosure section shows the business purchase price as $1.1 million. It does not include a price for the real estate. According to town records, the 7,254-square-foot building, portions of which date from the 1850s, and 16,542-square-foot parcel have an assessed value of $1,749,500.

Selectmen will hold a hearing on the transfer request on May 20 at 6 p.m. at the annex.