Looking Back At Troy Gentry’s Legendary Appearance At A Quincy Tavern

Let’s be honest here: it’s not often than chart-topping musicians come to Quincy. And when they do, more times than not they’ll do their 75-minute set, an encore if you’re lucky, and maybe sign an autograph or two before heading back to the bus/hotel and gearing up for their next stop (likely in some much bigger city on some much bigger stage with some much bigger money attached).

This was not the case with Montgomery Gentry who, in 2012, gave a bar full of Quincy patrons a night they’ll never forget; a night that likely made the news of Troy Gentry’s unexpected passing on Friday that much more heartbreaking for the Gem City.

If you don’t recall, the guys were in town to play the Dot Foods Christmas party at the Oakley-Lindsay Center. As is always the case with these parties, their appearance was strictly invite only and largely hush hush (our old buddy Doc Holliday claims it was the first secret he’d ever kept). After the show, Troy and Eddie set Q-Town social media ablaze when they stopped by the old Holler and Swaller Saloon down on York Street.

I recently caught up with a buddy of mine, Jon Graff, who was manning the taps that evening to see what it was like having two of country music’s biggest stars throwin’ em back with the Quincy masses.

“My boss informed me that they convinced Montgomery Gentry to stop by,” he says. “We were all super excited.”

Jon says that Troy and Eddie were courteous and shared their time with every single person that wanted to shoot the breeze over a drink. He says they praised small towns like Quincy for making their dreams possible, and Troy in particular was amazed at how quickly the bar filled up in practically no time whatsoever.

“Before they even arrived, the building was packed,” Graff says. “In a small town, news travels fast and it was obvious. When they arrived they came in with open arms—it was like they were regular customers coming in the doors.”

“Troy was so humble that he didn't just thank us for our time but he made us all feel at home, as if it was no big deal that a big time band like them were there,” Jon says. “Montgomery Gentry honestly made our small town bar feel like we were big time.”