On Saturday evening, January 31, 2026, The Scholarship Foundation of Wakefield, Inc. (TSF) proudly hosted the 34th Annual Trivia Team Challenge (TTC) at the Wakefield Lodge of Elks. Thirty-six teams—including five rookie teams—took part in an evening filled with friendly competition, challenging questions, and camaraderie. In their third year as Trivia Co-Chairs, Tricia Desrocher and Kelley Chapman noted that participants and attendees alike enjoyed a memorable night of teamwork and fun.

As always, the competition was spirited, with both veteran and rookie teams vying for top honors. Claiming first place was Pug Mom Strong, captained by Jack O’Leary and joined by family members Sarah, Mark, and Timothy O’Leary.  Finishing in second place was 4 Leaf Clovers, the 2025 Rookie of the Year Team, continuing their strong performance. Team members included Sheila Eriksen, Barbara Cassidy, Frank Cassidy, and Tim Sweeney.  Rounding out the top three was Eponymous, longtime participants and perennial contenders, who just edged out 2025 third-place team La Casas. The Eponymous team included Lucy Skeldon, Lauren Crews, Dan Crews, and Alex Skeldon.  This year’s Rookie of the Year Team title was claimed by the team of Just Like Matt Murphy’s, which was comprised of Greg Flynn, Steven Tulloch, Carrie Flynn and Lauren Tulloch.

TSF President T.J. White kicked off the evening by welcoming the participants and expressing gratitude for their support of this year’s Trivia Team Challenge, which will help fund awards to Wakefield students in June 2026.  

The evening was moderated by Michael Kilkelly, who along with his wife Susan, was responsible for crafting the questions that made the evening a fun and challenging event.  Teams competed in three 25-question rounds, with the top-scoring teams advancing to the fourth and final round.  Question topics included sports, entertainment, geography, history, literature, pop culture, and picture identification.

Generous event sponsors of this year’s TTC were One-on-One College Consulting, Reading Cooperative Bank, The Savings Bank, and William Blair.  TSF of Wakefield appreciates the support of these organizations and the role they played in the night’s success.

There are many additional individuals without whose hard work and attention to detail an event the size of the Trivia Team Challenge would not be possible.  A special thank-you goes out to our emcee and question team of Michael Kilkelly and Susan Kilkelly; to Linda McManama, Cathy Wensley,  Gayle Wettach, Cathy Donovan and Jean Maio for coordinating the raffle table; to Kathy DeCosta for chairing the snack table with many desserts donated by the TSF directors; to Jo-Anne Bourque, and Kathy Scanlon for handling pizza orders and sales; to Katie Fallon and Theresa Guanci for being our official greeters; and to Frank McLean and Rick Desrocher who took on the role of scorekeepers for the night, and again to Frank for all the heavy lifting and equipment setup prior to the start of the evening.   Lastly, we thank Dave Miller for again this year taking on the very important role managing the digital display of questions and scores throughout the evening.

We are grateful for the enthusiastic high school volunteers who assisted during the evening, under the supervision and guidance of Meg Delory Leahy and Becky Lamarre. The TSF student directors helped in setup and cleanup as well as during the event passing out picture questions, collecting answer sheets, and helping in the drawing of the winning raffle tickets.  The students also posted outstanding updates on Instagram throughout the night.  Thank you to the student directors who assisted us: Katelyn Bergeron, Madelyn Bergeron, Brandon Meahl, Evan Buonopane-Cohen, Savanna Bui.

Co-Chairs Tricia Desrocher and Kelley Chapman also thank TSF Administrators Anne Miller and Jennifer Walter for their work behind the scenes. The preparation before and after the evening is crucial and proved to be “the glue of the event.”  They both ensured that everything from the early planning to the wrap-up was beyond precision. The co-chairs added, “we can’t thank them enough for the over-and-above role they played in this year’s Trivia Team Challenge.”

Following the second round of questions, raffle tickets were drawn and the lucky winners were notified of their prize just prior to the start of the final round. There were many terrific prizes and our thanks go out to those who generously donated or procured a prize including Lisa Erban, Jay Pinette, Jo-Anne Bourque, Gayle Wettach, Katie Fallon, Linda McManama, Rich Bondi, Beth Sullivan, Tricia Desrocher, Jean Maio, Cathy Donovan, Mary Anne Power, Lucy Skeldon, Cathy Wensley, Kathleen DeCosta, Faith Hodgkins, and Kelley Chapman.  Thanks also to T.J. White for the outstanding donation of Bruins tickets. 

The popularity of the event this year was no doubt aided greatly by the publicity offered by local media. Thank you to Jon Pinkney and the Wakefield Daily Item for assistance promoting the event. Appreciation is also extended to Ann Hadley of JC Marketing for taking photos during the night. TSF extends a special thanks to WCAT and Ian McDermott for the use of projection equipment and setup assistance that was vital to providing the visual presentation. 

The 34th Trivia Team Challenge was a tremendous success thanks to everyone involved. The co-chairs wanted to give a big thank you to the Wakefield community and beyond, adding: “the support of events such as Trivia night is a testament to the ongoing support TSF receives from so many. We were grateful to continue this tradition and we look forward to many more nights like this.”