The Iconic Chatham Squire

The motto of the Chatham Squire, “Where friends get together,” says it all.

Author’s Note: There is no better ending to a summer weekend on Cape Cod than catching a Sunday evening Cape league baseball game at Veteran’s Field in Chatham. Recognized by fans and team volunteers as one of three top fields in the league (the other venues being Cotuit’s Lowell Park and Orleans Eldredge Park), there is always a good vibe under those bright lights. In the distance, behind the Chatham Fire Department, the setting sun signals the rush of the day has long passed, and a bounty of colors swirl in the sky amid a gentle salty, twilight breeze. Unique to Sundays, most day trippers and week-long vacationers have vacated the peninsula as they raced to get over the bridges hours earlier. And as fans settle into their seats after the singing of the national anthem, the “crack” of a first pitch fastball hitting the catcher’s mitt can be heard all the way down the first base line. Play ball!

While this scene was replayed on a recent Sunday evening, it was not until the end of the 7th inning when the real excitement began. Oddly, the excitement did not occur on the playing field. Chatham, like all Cape league teams, does a 50/50 and ‘handful-of-prizes’ raffle at the end of the 7th inning to raise money and keep fair-weather fans in their seats for the tense moments of those last innings. The raffle prizes range from harbor cruise tickets, specialty dessert vouchers, restaurant gift cards, and of course, half the cash collected. A few innings before the drawing, “bogey brother” Dan had to leave the game early and tossed his raffle tickets to us on the off-chance one would be a winner. Not only was one of his tickets called, but the prize was friend-favorite, a $50 gift card to the Chatham Squire (and two tickets on a Hyannis Harbor cruise). There could not be a more appropriate raffle prize, given all of our years of patronage. (Yeah, let’s go with patronage.) The best part of the ordeal was the delivery of the prize; kicked-off with a cryptic text message as soon as the envelope was received, followed by a stop at his house for delivery during a family nightcap on the porch. The astonished look of, “you’re joking,” was as glorious as expected. Later it dawned on me that the Chatham Squire donates this same gift card every home game (22 games per season) for as long as I can remember, which adds up to an $1,100 annual donation just to one organization. It’s also a good example of why a 51-year old restaurant is embedded in the fabric of Chatham’s community.

Indeed, a great 50-year run for Richard and George.

Much has been written about The Chatham Squire, as 2018 marked the legendary establishment’s 50th Anniversary. It also marked the last year of original ownership, as Richard Costello and George Payne, who started the restaurant and tavern in 1968, sold the business to Todd Hearle, a Connecticut businessman who grew up in Chatham. Fortunately, the intent is to change little, if anything, with the general manager and executive staff and many floor staff staying on. While it has only been two months since the change in ownership, I haven’t noticed any changes.

These license plates on the east wall of the tavern also says it all!

Now that the news covering the Squire has subsided, it’s as good a time as any for another long-time fan to chime in. Anyone who claims to know “about Cape Cod” surely has spent some time at this iconic Main Street destination. Whether elbowing your way to the tavern bar, listening to live music/trivia/karaoke from the table tops “upstairs,” enjoying a ‘quiet’ dinner in the dining room or getting rowdy in the back bar on a busy summer Saturday, The Squire has it all.

The collection of nearly 500 license plates from around the country along the tavern walls speaks to the come-as-you-are vibe. That diversity of experience is what makes the restaurant unique – plus the chowder is great, steamers do not disappoint, and I always seem to run into someone I know there. Admittedly, in the height of the summer season, it can be total chaos and you may want to avoid the lines and elbows. But during the day time, weekdays and especially shoulder seasons, its the local pub to have a good meal or drink at a good price. 

A hearty bowl of clam chowder and a cold draft beer are required starters, if you like that kind of thing.

In addition to the Chatham A’s, the Chatham Squire also supports many community events. The Squire’s logo can be found as a sponsor for First Night Chatham, both spring and fall Harbor Run/Walks (as after party host), on a float in the 4th of July Parade, and through many Chatham Chamber of Commerce events. 

Like many others, the Shaw and Healy crews are long time patrons of the Squire – especially in the winter months!

Having spent much of every summer in Chatham since 1983, I’ve put in a good chunk of time at the 487 Main Street property. As a kid, I recall a stern “mind your manners” moment while dining with my parents and grandparents in the main dining room. I remember staring at the ‘swinging door’ that endless hostesses, wait staff and patrons passed through, wondering what was back there.

As it turns out, “food” was behind the swinging door. The swinging door connected the dining room to the kitchen and to the tavern.

As a teenager, I recall catching a bite with my parents and brother in that once buzzing dining room, now nearly deserted, during a winter weekend. Snow was in the forecast, but had not started by the time we were seated. An hour or so later – and oblivious to the wet doormats and howling wind, we walked out into a full blown blizzard! The scene was magical. There were only parked cars on the road, and a handful of brave souls trying to get inside or to their car. the street lights and flood lights of each building illuminated the blanket of freshly fallen snow. As we slowly made our way to the car, wind gusts were swirling snowflakes in every direction on that chilly night.

As an adult, well, there were many nights started, continued, or finished at the Squire. A certain Squire loyalist (not me) also spent an evening of his bachelor party weekend at the Squire and may have been one of the most entertaining nights of my life. 

An old photo of The Chatham Squire from the late 1970s. Photo credit: The Chatham Squire.

Perhaps the most memorable experience at the Squire was the pending joy of standing in a 30-person deep line waiting to get into the tavern. It was the Saturday of Labor Day weekend…in 2002…I had just turned 21 years old. Admittedly – and this may come as no surprise – this was not the first time I’ve been in the Squire tavern. Cheers!

What is your most memorable experience at The Chatham Squire?