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Winchester Foundation for Educational Excellence hosting 23rd Trivia Bee

The BeeLTs from last year’s Trivia Bee dressed up as a combination of a bee and the ingredients of BLTs, bacon, lettuce, and tomato. COURTESY PHOTO/MAGGIE VANDE VREDE

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Winchester’s brightest fifth graders and adults will gather soon to compete in a fierce trivia competition that will raise money for Winchester schools.

The Winchester Foundation for Educational Excellence (WFEE), a nonprofit that provides grants for Winchester’s public schools, will host its 23rd annual trivia bee March 11 at 7 p.m. in Town Hall.

Each adult team pays a $375 registration fee. Usually, the event raises between $16,000 and $18,000.

The money goes toward grants in Winchester Public Schools. Grants have funded experiences and resources for students, including a visit from an archaeologist and new biotech equipment for science classrooms.

The event begins with five teams of three fifth graders – one team from each of the five elementary schools competing in a round of trivia for a trophy, a stuffed bee sitting on a plaque, that will be kept in the winning school for a year.

Last year, the fifth-grade team from Lincoln Elementary School won the fifth-grade Trivia Bee round. COURTESY PHOTO/MAGGIE VANDE VREDE

Then, teams of three adults take to the floor to compete in seven rounds of trivia, with the winners of the first five rounds competing against one another in the remaining rounds. There are usually 56 teams for the adult portion, and the winning team will receive a trophy.

“It’s a really incredible community event that brings together people that would normally never be in the same room,” said Maggie Vande Vrede, the foundation’s executive director.

This year’s emcee will be Britney DeLorme, the head of the children’s services at the Winchester library. DeLorme will create questions for each of the trivia categories including pop culture, geography, history, sports and literature.

Volunteers often dress up as bees, and attendees are encouraged to dress up as well to win the costume contest that runs alongside the event.

In the past participants have dressed up in bee-themed costumes, while others have gotten more creative.

Elana Rudiger, president of the education foundation, recalls a team dressing up as Wednesday Addams of “The Addams Family” a few years ago. Vande Vrede’s favorite was when a team, the BeeLTs from last year’s bee, dressed up as the ingredients of their namesake.

The trivia bee is open to all, drawing in a crowd not just of competitors but also of onlookers, who come to cheer on their favorite teams.

Last year’s winners were Lincoln Elementary’s fifth-grade team and the Parental Prodigies, the Winchester High School Parent and Faculty Association team. Winning the bee is a “great community honor,” Rudiger said.

John McMahan, a second-grade teacher at Lynch Elementary School, has been participating in the trivia bee consistently since he started at the school 10 years ago.

While the elementary school’s faculty team hasn’t won the bee, the fifth-grade team has. McMahan likened the atmosphere in Lynch that year to seeing Tom Brady win the Super Bowl.

“They show off what they know, which is obviously really cool as a teacher,” McMahan said. “But then at the same time, seeing them get so jazzed up for a community event I love.”

Last year, the adult trivia winners were the Parental Prodigies from Winchester High School. COURTESY PHOTO/MAGGIE VANDE VREDE

Though many go for their love of trivia, the fifth-grade trivia round is always beloved by the crowd.

“There’s a lot of pride there and a lot of excitement,” Vande Vrede said. “They always bring a crowd.”

While trivia is competitive, the atmosphere in the town hall during the bee is lighthearted. Attendees quickly overcome their nerves once they sit on the trivia stage.

“No matter how stressed out you are, you realize you’re doing it for fun,” Rudiger said. 

Though the Trivia Bee tests competitors' knowledge, it is also widely loved for the way it builds community within Winchester.

“It’s one of those things that not every town has, but every town should because it's just such a fun way to get the community together,” Rudiger said.

Tavishi Chattopadhyay is a journalism student at Boston University. This story is part of a partnership between Winchester News and the Boston University Department of Journalism.

Winchester News is a non-profit organization supported by our community. If you appreciate having local Winchester news, please donate to support our work, and subscribe to our free weekly newsletter. Copyright 2026 Winchester News Group, Inc. Copying and sharing with written permission only.

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