Martha’s Vineyard trivia nights

Ralph Stewart

Trivia is the Island’s winter sport of choice: Tuesday at The Newes and Wednesday at The Wharf in Edgartown, and Thursday at the Portuguese-American Club in Oak Bluffs.

Three different venues, three different crowds. Same game. The fans, more than 150 a week combined, love it. Fun is the motivator.

Main Street in Edgartown can be a lonely place at 8 o’clock at night in January. The summer shops are dark. Parking spots, so prized in August, yawn endlessly ahead.

Not on Wednesday night. During Trivia Night at The Wharf, the front bar is speckled with a few patrons sipping Buds and watching the Celts, diners linger here and there in the main dining room. But walk into the back bar and you are enveloped in a blast of energy and noise.

On a recent Wednesday night in January, Dan Cassidy, garbed in his beloved Chicago Bears football shirt, was warming up a crowd of 80 trivia players with a personally mixed playlist of rockin’ tunes. His mom, Pam Cassidy, “my lovely assistant” as Mr. Cassidy invariably introduces her, is inputting team names on a score sheet displayed on a big screen above the stage where she and Mr. Cassidy are perched at the entrance to the back dining room.

Mr. Cassidy plans the weekly events, often matching music and 40 to 50 questions around a theme. He’s used Michael Jackson, the ’80s, Country and Western, and is dressed appropriately on theme night. “We use the Stump! trivia service. They send the questions and I review them for categories and a theme if we have one that week. I try to organize the music playlist around the theme, music I think everyone will enjoy.

“I saw this in Boston once and researched it. I talked to Will [Coogan], The Wharf owner, two years ago and we got going. It’s a fun thing to do, a chance to socialize in winter and everyone can do it. For the regulars, it’s a planned night out. It doesn’t matter if they win or lose. It’s about socializing,” he said. First place team gets a $50 Wharf gift certificate and second place receives a $25 certificate.

Every booth and every table was filled with teams for the Stump! trivia quiz. Up to six players a team, no charge to play. More can be on a team, but only teams up to six are eligible to win. Teams change and morph every week.

On this particular Wednesday, the packed house looked like a typical August night. “Except that you might look into the room in August and recognize one face. Everyone in here tonight knows each other. It’s a community event,” says Jeff Voorhees, restaurant manager.

Mr. Voorhees likes what he sees, not just because he’s got business. “This room would be dark if it weren’t for trivia,” he acknowledges, but he likes the energy and the fun. “People are enjoying themselves, having a night out with their friends and neighbors. Not always easy these days,” he says.

The Wharf’s take will be a fraction of an August night when tables turn two or three times with much larger tabs. Some trivia players order dinner but most will spend three or so hours with a couple of drinks and maybe an appetizer.

Late-arriving teams often overflow into the main dining room. On those nights, Mr. Cassidy, an Oak Bluffs police officer, has to turn and repeat the questions to the far room. Mr. Cassidy is a big draw. “We had trivia on Thursday night last year because that was Dan’s night off. This year he has Wednesday off,” says Mr. Voorhees.

Host Ray Whitaker, of WMVY radio, runs 1, 2, 3…to Knowledge weekly at The Newes, starting at 7 pm. Mr. Whitaker researches and writes his own questions, which sometimes involve sound clips from songs and movies, for the weekly themed trivia nights.

According to Mr. Whitaker, “It’s like hanging out in someone’s living room for an informal game of trivia.” There’s no cover charge.

The Portuguese-American (P-A) Club has trivia on Thursday, host Gary Buckley explained on the following night. “It’s not a competition thing. We had it on Wednesday night last year but switching to Thursday to accommodate was no big thing,” he said. “It’s something for people to do and a fundraiser for our Benevolent Committee,” said Melissa Randall, his co-host.

Jeannie Holenko, a teacher at the Oak Bluffs School, has been to both The Wharf and the P-A Club trivia nights. “The two nights are different. Here at the P-A the games are more rapid fire than at The Wharf but I enjoy both of them,” she says.

Mr. Buckley and Ms. Randall fire out 10 rounds of questions, each round containing 10 questions, not including bonus questions, packed into two and one half hours. Like The Wharf and The Newes, the crowd is multi-generational, from 20-somethings to youthful grandparents. At The Wharf, teams field fewer questions because the crowd is busy hooting at Mr. Cassidy’s Bears jersey and listening to the music between questions.

The P-A game charges $5 a head. Teams can have an unlimited number of players, and the winners share 50-50 with the club. The winning team often receives $100 or more. Runners-up get tee shirts, key chains, “whatever we have in the basement,” Mr. Buckley grins.

Often the winnings are donated back to the club. Cheryl King, a P-A club director, said “A couple of weeks before Christmas, we were talking about how The Red Stocking Fund needed money during trivia and the winning team just donated the whole pot, $125, to Red Stocking,” she said.

“People know the proceeds go to our charitable committee. Trivia’s been a good membership tool. People come to play and join the club,” Mr. Buckley said as he prepared to fire up a final set of questions to the several dozen players on Thursday.

The night before, Mr. Cassidy was having trouble getting his final set of real questions asked because he was being belted with jeers, wadded napkins, and paper balls for asking this bogus question: “Which NFL team went 18 and 0 and lost to a New York team in the Super Bowl?”

It was the only question of the night for which everyone in the room had the sadly correct answer.