Fascination With Facts Fuels Kerry Spencer’s Trivia Mastery

Kerry Spencer grew up in a Brewster family where there was always a “push for knowledge.” Books were Christmas presents, she says, and if you weren’t familiar with a word or topic, you checked a dictionary or encyclopedia.

She read her grandmother’s pop culture and gossip magazines, too. An ‘80s kid, she watched a lot of movies and TV, and she became a regular “Jeopardy” and “Wheel of Fortune” fan. Even today, Spencer says, she has “way too many ‘80s song lyrics in my head.” 

At New York’s Siena College, she earned a history degree. Travel generated interest in geography. And Spencer attributes all of that varied background to fueling her 15-year role as Quizmaster Kerry.

Her paying jobs during that time have involved bartending, serving, and handling social media at the Chatham Squire restaurant and in recent years La Bella Vita Kitchen and Bar in Orleans. But every week, Spencer, 51, has also run a trivia night — first at the Squire, then virtually during the pandemic, now at the Red Nun Bar and Grill in Dennis Port.

She’s proud that the contest regularly brings in 50 to 80 people, sometimes more, and often requires adding servers on a shift. 

 “It has a community feeling to it, and there’s a lot of friendly competition, with banter back and forth,” says Spencer, who posts highlights on her Quizmaster Kerry Instagram. “So many people say this is their social night of the week. There are people who are 21, or in their 80s, and I work hard to make it inclusive for everybody.”

Her quizmaster days began when the Squire planned a trivia game when those were becoming popular at bars, and Spencer and friend Drew Downing offered to host. After honing the best way to ask questions and what participants most enjoyed, Spencer later continued on her own and now estimates she spends at least four hours weekly preparing questions and games.

While studying history, “I was used to doing so much research,” she says, and jokes. “This is just like doing research, but instead of becoming a teacher or lawyer, I became a trivia host.”

She tries to never repeat a game question — checking herself on long Google docs that catalogue what she’s asked. That’s important in part because her games have fans who have followed her September-to-May seasons for the entire 15 years — moving from the Squire to the Red Nun and even online in 2020-21 when large public gatherings were banned or discouraged.

Online pandemic games attracted not only Cape regulars but Spencer’s far-flung friends, siblings, college roommates, and even a Malaysian team who got up at 7 a.m. to play. 

 “I made this little studio in a corner of the room, made a sign, and it looked like a 1980s ‘Wayne’s World’ situation,” she says with a laugh. Some teams would gather on Zoom, then participate through Spencer’s Facebook Live event. “People would message me their answers,” she remembers. “I think it gave people community at that time, and a place to meet up with their friends, even though it was just over Zoom.”

Spencer enjoys facts and information enough that she sometimes tests her own skills by going to other trivia nights locally or while vacationing with friends. For Red Nun Thursday-night games, she offers four main rounds with four questions each about music, movies, TV, sports, history, and geography. Other topics — art, science, business, Cape Cod, National Parks and more — rotate in to try to address various people’s strengths.

Visuals are also important to Spencer, whose creative outlet is Cape photography, which she posts on Instagram as kerrycapecod. Her bonus rounds for trivia games usually involve identifying images — childhood photos of celebrities was a recent challenge. Spencer also adds questions marking events like the Super Bowl, Valentine’s Day and Halloween, then creates themed nights for Christmas and a year-end review. Final 25-point questions can make all the difference in declaring top winners, who are awarded gift certificates ranging from $50 to $20.

Between rounds, Spencer plays music, which changes weekly. “It’s a lively room, not just ‘Here’s your question,’” she says. “I try to keep the music pretty upbeat, so the energy in the room is upbeat.”

Teams of up to eight people with names like “Quizzards,” “Hocus Focus,” and “Cell Phone Cheater” have different goals. “Some people are real trivia enthusiasts and they're there for trivia and want to win,” she says. “But some teams just come out to be with friends, have a laugh, have some beers, and talk about stuff other than what's going on in the world, or their family, or their life, and have camaraderie.”

Camaraderie for her, too. After returning to Brewster in the late ‘90s to care for her grandmother, Spencer’s circle of friends include many people in the Cape’s close-knit restaurant industry. But she also considers some trivia regulars her friends. 

 “You live in these small towns on the Cape, and it’s really a great local community,” says Spencer. “A night like that kind of shows it and makes it shine.”