While some may find it odd that there’s a bar underneath one of the largest first-year dorms on Pitt’s campus, but according to JB Brunton, a manager at Hemingway’s Cafe, the bar most likely pre-existed the Litchfield Towers above it. 

The Pirates used to play on Forbes Field, located where Posvar now stands. Across the street, Pirates player Frankie Gustine ran a bar called Frankie Gustine’s, which was sold in 1983 and became the well-known bar it is today. 

“He was one of the owners and he worked here, but it was called Frankie Gustine’s,” Brunton said. “And so he would go play and then his kids would be here and like they would work at the bar.”

Wednesday at 6:30 p.m. might not seem like the busiest time a college bar sees, but it is for Hemingway’s. On Wednesdays, the bar hosts a weekly trivia contest, which draws in tons of local Oakland residents. Lily Young, a senior computer science major, said she loves going to Hemingway’s for trivia on Wednesdays.

“My friends love doing trivia, and I like to join when I can,” Young said. “It’s a great time to hang out and catch up with my friends and it’s something fun to do in Oakland on a weeknight.” 

However, Hemingway’s wasn’t always known for its trivia and pitchers. According to Laura Smeltzer, a Dietrich alum from 1996, when she was at Pitt, Hemingway’s was a fancy restaurant operating under the same name. 

“Hemingway’s was a very bougie, upscale, white tablecloth restaurant,” Smeltzer said. “Yeah, I’m sure it’s really hard for you to imagine. I mean it was very, very upscale. In fact, that was where I had my graduation dinner with my family.” 

Since then, the owners of Hemingway’s have switched, Smeltzer said she was very surprised when she first came back and saw Hemingway’s as it looks now.

“I remember I was gonna go to Hemingway’s and get soup and salad because I remembered it was so good, and I walked in there and I’m like, whoa,” Smeltzer said. “Because it had been a couple of years and it must have been when they kind of transitioned over. I thought ‘Oh my gosh, this is not the same. Like this is not the same at all.’”

Bruton has worked at Hemingway’s for about 10 years, but he said one of his most memorable nights was working when Kenny Pickett was drafted. He remembers the energy in the room and described it as the noisiest night he remembers working.

“I think the Steelers had the 20th Pick and somebody else 17 or 18 was kind of in the market for a quarterback and didn’t draft one, and everyone went crazy,” Brunton said. “But then the Steelers were up, and they drafted Kenny and it was like pandemonium in the air. I’ve never heard it louder in here.” 

John Bone, a bartender and bouncer who has worked at Hemingway’s for just over a year, said one of his favorite nights he’s had working at Hemingway’s was last year during Pitt’s run in the March Madness tournament. He remembers working the night of Pitt’s game against Iowa State. 

“It was a very close game that came down to the end, and right when the final buzzer goes off, Pitt wins,” Bruton said. “Everybody just started jumping up and down, and there was just glass shattered everywhere because people just kept dropping their drinks. So it was fun in the moment, and then five minutes later, I had to go and clean up like so much glass everywhere, which was a little annoying, but you know, yeah, I had to do what I had to do.” 

Though many know the bar for its mixed drink pitchers, there are plenty of other drinks to try no matter the occasion. They are open Monday through Wednesday from 4 p.m. to midnight, and Thursday from 4 p.m. to 1 a.m. On Friday and Saturday, they’re open from 11 a.m. to 1 a.m.

All of their pitchers typically cost $9, but some are $5.50 on select days. Their most popular pitcher is the Long Island, which is the Thursday special, and is one of the “strongest” pitchers, according to the owners. Other popular pitchers served include the Pink Whitney, Spiced Rum and Coke, the Olivia Rodrigo, Cathy on Acid and the Kenny-Spritz-ett.

Paige Buenaga, a senior film studies major, said she thinks Hemingway’s has a great location and that she often comes because it’s easy to go after a long day of classes.

“If you’re tired after a long day, you don’t have to walk that far,” Buenaga said. “But it’s also cool, they’re really nice and it’s relaxed. I like it.”