The Chatham Squire Celebrates 50 Years

The Chatham Squire, a town institution, celebrates five decades of merrymaking, good food and memorable times.

Written by Lisa Cavanaugh

In the summer of 1968, a 12-year-old Chatham boy tired of mowing lawns went to the back door of a newly opened restaurant on Main Street to ask for a job. The cook, who just happened to be the brother of one of the owners, asked him a couple of questions. The boy told one lie, claiming to be 14, and one truth: His name was Mike Wade. “Well, I’m Mike,” said the cook, “and we have another Mike here already. So you can be ‘Pork Chop’ and you can start right away.”

The nickname stuck as Wade became one of the very first employees of the Chatham Squire, a town institution celebrating 50 years of food, drink and communal merriment. “I can’t imagine what the over/under odds would have been then of two young guys from Boston making it all the way till now,” says Wade, referring to Richard Costello and George Payne, the founders and co-owners of the Squire (as it is colloquially known). But make it they have, providing a half-century of good food and fun for everyone from the locals of Chatham to visitors from around the world.

George Payne and Richard Costello | Photo by Michael and Suz Karchmer

“We worked together at the Branding Iron in Boston,” says Costello, who started in the restaurant business as a cook. “George was a professional bartender who knew what he was doing.” Payne’s grandmother lived in Orleans and he had always liked Chatham, so when the opportunity came up to lease what was then The New Yorker Restaurant, Payne and Costello, just 27 and 26 respectively, decided to go into business together. They officially opened The Chatham Squire in the section of the building that is currently the dining room. “We tossed a bunch of names around and that one stuck,” says Payne.

The young partners had a lot of work to do. They pulled up the linoleum floors and upgraded the kitchen. They didn’t have much money for improvements, but they had a lot of friends, from Boston and the Cape, who volunteered to help. And the regular clientele, intrigued by the new ownership, continued to come in for dinner and drinks. “George made their drinks just as they liked them,” says Costello. “We brought in musicians and we were having a wonderful time.”

That first summer was a success, and by September word of just how well they were doing had reached their landlord—through a citation from the Chatham Police. “We had people living upstairs in what is now the office,” says Costello. “The day after Labor Day the landlord, who I’m meeting for the first time mind you, arrives with a police report about a big celebration the night before. Our names aren’t on it, although we’re the only ones supposed to be living upstairs. Basically, he gave us the choice to get out or buy the place.”

Buoyed by youth, confidence and support from friends in the banking business, Costello and Payne financed the purchase of the entire building, eventually taking over the adjacent retail stores to open the tavern side of the Squire. On opening day in the spring of 1968, there were at least 100 people lined up on the sidewalk waiting to come in, recalls Costello. “It was mind boggling to be a part of it.”


Although they initially only had an April through November liquor license, they soon operated year-round, despite everyone thinking they were crazy to stay open in the winter. “In those days, if you walked outside the day after Labor Day, you could wait 10 minutes, no exaggeration, for a car to go by,” says Payne.

“And it was a good chance you’d know who was driving the car!” laughs Costello.

They made serving delicious food, especially seafood, a priority, and created a niche for themselves among the establishments on Main Street. The friendly atmosphere appealed to everyone. “The two front tables would be full of local people playing cribbage all winter,” says Costello, “and the fishermen were our saving grace in the early days.”

The key to their longevity has been rooted in that homey sense of belonging, for both customer and employee. Wade, who started as a dishwasher, worked summers through high school and college and ended up managing the bar before leaving to become a successful magazine publisher. He credits his experience at the Squire for his work ethic. “It is thanks to the lessons I learned there that I was able to succeed,” he says.

Costello explains their simple but effective approach: Customers are welcomed and thanked, and the staff can be themselves. “We want our employees to be able to laugh out loud and have a good time,” he says, “as long as they take care of the customers.”

As the Squire grew in popularity, so did the crowds. It became a regular sight to see lines of people outside on a weekend night, as eager patrons vied for spots at the bar. Sarah Varney Muto, who, along with her brother, worked for many years at the Squire, recalls the electric atmosphere. “It was so much fun, but you had to keep up with the pace of the bar while maintaining your sanity.”

While the Squire is renowned for its customers’ boisterous merrymaking with live bands and dancing, it was even more raucous in years past. Costello and Payne give particular kudos to former longtime bartender Amy Tagliaferri for her skill in managing a room full of partiers. “She was the best,” says Payne. “Amy could handle the whole place without batting an eye.”

Tagliaferri, who now works for The Cape Cod Chronicle, has fond memories of a former era when a lot went on behind the scenes. “Back then, there was a Wild West feel at times, but management always had our back,” says Tagliaferri. She points out that Costello and Payne have long supported the staff with full benefits and perks like health club memberships. “They are always working for their employees,”
she says.

Early ‘80s

Dozens of staff members stay for decades, sometimes leaving for years only to return for Round 2 of life at the Squire. Wade retired from publishing in 2004 and now tends bar occasionally, having returned to the Cape when his sister Wendy, who happened to be Costello’s wife, fell ill with cancer. Wendy, who succumbed to the disease a decade ago, met her future husband by giving her younger brother a ride to work on her bike.

“I met my own wife here, too,” says Wade, echoing a love story that has been repeated time and again at the Squire. The same is true for Payne, whose wife was a chef at the restaurant, and whose two sons worked there as well. Chris Matheson, who is the current bar manager, also met his wife on the job. “Lots of Squire employees fell in love and got married,” says Matheson, who started there in 1992. “It is part of what makes this place special.”

The owners are proud of the connection their staff and customers have with their business. From the hundreds who come to snap photos of the iconic license plates that adorn the walls (“They are all given to us and people come back to find their plate,” says Payne) to the brides who want to end their wedding celebration with drinks at the bar, the clientele have been joining the employees in one big, happy Squire family for 50 years. “Everyone comes back,” says Costello, “and when they come back, everyone feels young again, everyone feels Cape Cod again, everyone feels Squire again.”