How Do You Spell Success?

The Wellesley Education Foundation’s Annual Spelling Bee Provides Fun and Funds

Cheryl Fenton writer

As fall takes hold of New England and the leaves begin to turn, there’s a buzz around town. Beyond vacation plans and holiday get-togethers for the calendar, the talk in Wellesley centers on a single night in November. It’s a great time. Or shall we say it’s s-u-p-e-r-l-a-t-i-v-e.

It’s time for the much-anticipated Wellesley Spelling Bee, an annual fundraiser sponsored by and benefiting the Wellesley Education Foundation (WEF). On the first Thursday of November, the Wellesley High School cafeteria is alive with excitement, peppered only by moments of silence as collective breaths are held and championships are decided over one word.

“It’s the best family event in town,” says Sandy Joseph, former three-time co-chair of the Bee. “It’s a community builder for sure.”

But this is not your kid’s spelling bee. It’s yours. Children sit on the sidelines as local businesses, alumni groups and community organizations gather together to match spelling skills. The youngest spellers are sponsored high school student teams, eager to beat out the older crowd, a feat performed in 2005 and 2006.

“A lot of children come to cheer on either their mother or father or their favorite teacher,” continues Joseph. “It gets kind of raucous, which is awesome.” Happy to go from Queen Bee to Worker Bee, Joseph now assists with a few of the event tasks.

For $450 (the tax-deductible fee to register a team), Wellesley coworkers, neighbors or fellow college alums test their skills in teams of three against fellow spellers, with the hope of bringing home a coveted trophy and winning a place in Bee history. If spelling isn’t their cup of “t,” sponsoring a team or making a donation is a welcomed option. Every team is matched with a generous $75 donation from both Babson and Wellesley Colleges.

In the Bee-ginning
The first Bee took place in November 1990, the brainchild of Ken Rossano, a WEF boardmember who had participated in a Bee sponsored by the Boston Adult Literacy Fund. To ensure a smooth run of the inaugural event, Rossano served as honorary chair.

As part of the Bee’s intrigue, they recruited a local celebrity as Master of Ceremonies. With five boys who went through Wellesley public schools, Mike Dowling, principal sports reporter for WCVB-TV’s NewsCenter 5, had a vested interest. He jumped on board and has been emceeing ever since.

“The first thing they brought up to me was that it was a fundraiser for Wellesley public education, so I thought that was a good idea,” he remembers. “I thought we could really have some fun with this.”

Everyone credits Dowling with the event’s light-heartedness, as he quips with contestants and adds ad lib humor to the evening. It’s this humor and popularity that has created another “face” beyond his high profile day job.

“I was stopped at the grocery store years ago, and someone looked at me and said, ‘I recognize you,’” Dowling remembers. “I said, ‘Well, I work at Channel 5.’ They said, ‘No, you host the Wellesley Bee, don’t you?’”

In our tried and true Red Sox Nation, there was even a time where sportscaster and Bee emcee worlds could have collided for Dowling, but thanks to a little teamwork it wasn’t a problem. “Last year we almost ran into a conflict with the seventh game of the World Series,” says Dowling. “So I told all the Red Sox players to take care of business in four games. They cooperated. Wasn’t that nice of them?”

Some might say the Bee is a sport itself. Excited, anxious spellers-to-be await turns at bat. A timekeeper clocks every second of play, while teams look to refs for close calls. Fans cheer victory in a standing-room-only venue.

“It’s completely packed,” says Illissa Povich, this year’s Queen Bee, sharing her crown with Bee co-chairs Robin Keeler and Michelle Arbeely. “That’s one of the cool things about the Bee. Little kids come and love it. Older Wellesley residents come and love it. It’s an intergenerational event.”

Within a world of yellow and black balloons and decorations, spellers and spectators alike munch on treats and sip cold drinks, all donated by charitable businesses and WEF members—sub sandwiches, Dunkin’ Donuts donuts, popcorn, coffee, tea, soda.

“People even bring in their leftover Halloween candy,” says Joseph. “It’s all on a back table, so anyone can go up and graze.”

There’s also a mascot, an addition made in 1995 when chairwoman Vickye Kivett and her Bee committee decided to bring the Wellesley Bee to life. Literally.

“I stitched together a costume that could be worn at the Spelling Bee,” says Kivett. “Based on the model of sports teams that have life-sized mascots in costume, I asked someone to be the Wellesley Bee. She had a wonderful time livening up the 6th Annual Bee.” The bee still buzzes around every year.

The Bee—From A to Z
The night begins promptly at 7:00 pm with approximately 50 teams, each made up of three members, participating in the Spelling Bee. There are seven first rounds, with seven teams in a round. The Chairs try to organize teams with common themes, such as a round of PTOs from each of the schools, real estate agents or law firms, along with an all-student round.

Even if you’re not competing, you might find yourself putting on your thinking cap. “Some of the teams change at the last minute, so there might be fill-ins from the audience,” says Joseph. “They might bring them up cold turkey, for instance if there’s a BC alum in the audience. People are very willing to help, if someone can’t make it last minute.”

The Bee runs in typical fashion, with the emcee reading off words, with definitions, if needed. Members consult with each other and have 25 seconds to write their decision on a white board, holding it up for the three judges (historically the superintendent and administrators) to view. And there’s no question when time is up. The Keeper of the Gong lets loose a gigantic gong, signaling pens down.

Throughout the round, words progress from easy (“tornado,” “punctual”) to moderately hard (“diminutive,” “scabbard”) to I-give-up difficult (“trypanosomiasis,” “mucilaginous”). But spellers aren’t left to navigate these waters blindly. A few weeks before, each is given a booklet of possible words, called the “paideia” (a Greek word that sent this writer scrambling for spell check).Words are culled beforehand by a committee and are given to Dowling to rack the brains of the contestants.

When a team misspells, it’s out. After each round has a winner, the championship begins. The best of the best compete with difficult words only.

“When you get to the championship round, usually the teams that win are the teams that have really studied,” says Povich. “After the easy words, you’ve never heard of most of the words.”

Povich has seen her share of tough ones (or not so tough ones, as it were). A speller on the Duke alumni team for years and in it strictly for fun and the benefit to WEF, she jokes about their inability to make it past round one. “If Duke knew we were doing this, they would make us stop,” she laughs.

Although the similarities between the Bee and a ballgame seem endless, the Bee itself is not. There might be an extra inning or two, but the game ends promptly at 9:00 pm, as the “pitches” become impossible to return—difficult words that even send an emcee who pronounces professionally searching for a judge’s help.

The Ruth Humphries Bee Trophy is the coveted prize for the winning team to keep for its reigning year. A plaque listing all of the winners hangs in the Wellesley Free Library. But no one walks away empty handed. Every participant receives a mug with the Bee’s name and date.

First winners
“For 17 years, I kept my pens in my Wellesley Bee coffee mug on the customer counter at our shop,” says Dottie Damon, co-owner, with her husband, of the former Linden Printing in Wellesley. She and her fellow teammates Dory Tappan and Mary Wolf correctly spelled “drisheen,” an Irish sausage, to become the Bee’s very first winners in 1990.

“I was very excited to participate in the Bee when it was inaugurated by WEF,” says Wolf, who is presently the secretary to the superintendent of the Wellesley Public Schools. It was only appropriate that a team with such intimate ties to public education as the Wellesley Public Schools Secretaries win an event that was to benefit that very institution.

“As an employee of the schools that were to benefit from the funds raised through this endeavor, I aspired to do well,” remembers Wolf. “It was the school committee that sponsored our team that year. I studied diligently in anticipation.”

Despite distractions, such as Tappan’s upcoming nuptials two days after the Bee, the team’s hard work paid off with the trophy.

Ann Rappaport, Katie Smith-Milway and Pamela Posey claimed the title of 2007 Wellesley Spelling Champs as the Wellesley Green Team. This trio represented a group of Wellesley citizens working toward energy sustainability for the town and particularly for a “green” building design for the upcoming high school project. Donning T-shirts boasting the word SMART (an acronym for Sustainable Management of Appropriate Resources and Technologies), these three women showed up with their spelling caps firmly in place.

“We joked about how embarrassing it would be if our SMART team gave a dumb answer,” laughs Smith-Milway.

But that never happened. Cruising through words such as “machicolation” and “escamotage,” the Green Team proved their abilities were anything but green. It must have been all that coaching from their Table Host that night, who, according to Smith-Milway, was filling the ladies up with popcorn to “carb up” for the match.

Dedicated prep work was the driving force behind the Green Team’s win, as it is with most teams who take home a victory. With kids quizzing them during drives to and from soccer games to a final drill with Rappaport’s husband as the announcer, families and friends came together for success.

Bee success can be measured in many ways, with trophies, plaques, and recognition. The greatest success, however, is the gift to the future of education.

Wellesley Education Foundation
“The Wellesley Education Foundation Spelling Bee is an amazing community event that has been greatly supported by Wellesley organizations and participants over the years,” says Kivett. “Every year, while there is new enthusiasm and participation from the Wellesley community, the spirit of the Bee remains the same.”

That spirit follows WEF’s mission—to enrich, enhance and maintain excellence in the Wellesley public schools. WEF provides grants to educators in the system, supports professional development and new initiatives, and assists programs already in place.

Grants go to the public school educators twice a year and run the gamut from pre-schools to high schools. Wherever the priorities are at the time, WEF’s challenge is to meet the need and even attempt to surpass it. According to the 2007-2008 co-president of the Wellesley Education Foundation, K.C. Kato, this past year saw more than $150,000 in grant money awarded. “It has been a great year for us,” she says.

“The fiscal reality is that education is funded pretty tightly, so there isn’t a lot of funding for new initiatives. And sometimes you also have to be in maintenance mode,” says Kato. This is where WEF steps in. Programs in the past have included a large grant for math professional development at the elementary level, a laptop initiative in the middle school, even a weather station at the high school.

Although it’s not its largest contributor of funds (WEF’s permanent fund is closing in on two million dollars this year, and they’re close to the $500,000 goal from a generous 2006 matching grant), the Bee is the largest event-driven fundraiser, raising an average of $27,000 annually.

“The Bee has been this great community event, and it’s wonderful that because of it, we raise a significant amount of money,” says Kato. “But it’s also just a great family event. We’re so appreciative of all the support.”

It’s this initiative that has created so much excitement and promise around the Bee. There’s something taken away by all involved, both spellers and audience members.

“Studying for the Bee reinforces that words are something we absorb, learn and ultimately can own,” says Posey. “In this day of dwindling readership, kids need to know that language is what helps to keep us civilized and words really do matter. They’re the currency of civilization.”

Povich agrees, adding, “[The Bee] is a really good example for the kids to see the adults up there taking risks, making mistakes, all these things that we ask our kids to do.”

And you might see a few familiar faces returning this year. When asked if they would compete again, last year’s champs answered in true Bee spirit…

Smith-Milway: “Y-E-S.”

Rappaport: “D-E-F-I-N-I-T-E-L-Y.”

Posey: “A-F-F-I-R-M-A-T-I-V-E.”

If you are interested in participating in, volunteering for or donating to the Wellesley Bee, please visit for more information or contact co-chair Robin Keeler at 781.237.3422. Entries should be received by September 30.

Summer 2023