Alumni Spotlights

Do you know of a classmate or fellow Alumnus who has found success in their personal or professional endeavors since graduation? Have you released a new album, joined a sports team, starred in a play, or authored the next great American novel? We will continue spotlighting graduates across the decades. Please let us know and share your story.  Email us at

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 David Seaver, Class of 2006
A bike trip across country led David Seaver to find a second career and home in Colorado.  More…



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Andrew Rotondi, Class of 1997
A move to New York City ultimately turned out to be a life changing experience for Andrew Rotondi. Living with his brother and friend in NYC, Andrew started to pursue his passion of writing, acting, and producing films. Two years ago, Andrew moved back into the area to Medford, where he continues to write and sell real estate. His experiences at Winchester High School and in the community have helped shape him as a person but also professionally in his writing. More…


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Catherine Arnott Smith, Class of 1977
Catherine Arnott Smith, Class of 1977, is a professor at the University of Wisconsin-Madison, where she has been since 2006. Catherine lives with her husband, Mark, a professional musician, and son, Simon, in the small city of Stoughton, 20 minutes from Madison and perfect for a combo of car and bike commute to her office. More…

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Summer Holcomb Rothwell, Class of 2002
Winchester High School graduate Summer Holcomb Rothwell has always been about the pursuit of happiness, even if it took non-traditional ways to get there. After graduating from WHS in 2002, Summer went halfway around the world to get her undergraduate degree at the University of Hawaii at Manoa. Before focusing on her family and her two sons, Summer worked in business and fashion. More…


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Elizabeth Doherty, Class of 1985
Elizabeth Doherty’s passion to help others fueled her career change from working in an actuarial consulting firm to her current position as a pediatrician.
Doherty grew up in Winchester and now both resides and works in her hometown. While her time in college lead her into the business world for a number of years, she was determined to follow her heart into medicine. More…
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Tim Nolan, Class of 1996
After graduating from Winchester High School in 1996, Tim Nolan has stayed connected to his Winchester roots and immersed himself in the community that he has since moved back to. Nolan is the middle child of seven siblings, some of whom also still call Winchester home. His parents have 11 grandchildren in Winchester, which include Nolan and his wife’s three children: Winnie (6), Dennis (5) and Marty (1.5). He owns his own wealth management and financial planning practice called the Nolan Group. When he is not helping clients and their families work on wealth preservation, he and his wife are active in the community.


Jeff Vanderkruik, Class of 2003
Jeff Vanderkruik, a Winchester High School class of 2003 graduate, has been pursuing his passion for writing and telling jokes since his days at Winchester High School. After graduating from Tufts University, Vanderkruik made his way to New York City where he eventually worked on Saturday Night Live. From NYC and SNL, Vanderkruik went out west to Los Angeles where he is currently living and writing on the NBC sitcom, “A.P. Bio.′ Check out ‘A.P. Bio’ Thursdays on NBC or through the show’s website: The season premiere is Thursday, March 7, at 8:30 p.m.
Lauren (Pallotta) Stumberg – Class of 1999
Since 2012, Lauren (Pallotta) Stumberg has been living and working as an artist in Atlanta, Georgia. The 1999 graduate of Winchester High School has artwork, including a 90×90 mural, all over Atlanta. Lauren works as a designer, muralist, illustrator, and creative consultant. She also started Think Greatly as a platform to help organize female-driven projects. Once a stranger to the local art scene, Lauren has continued working on her craft and was named the 2017 City of Atlanta “Emerging Artist Award.” Lauren’s most proud moment also came in 2017 when she became a mother. Whenever Lauren is back in town, she makes sure that D’Agastino’s is her first stop. More …
 John Williams – Class of 2001
John Williams is a professional artist living in Winchester who creates complex collage portraits and landscapes using small pieces of cut magazine paper. John’s portraits include figures throughout history, depicting the character of the subject and a mini-history lesson of their times. He enjoys creating landscapes and floral images for fun. Williams, Winchester High School class of 2001, has done a number of solo exhibits in Florida, Washington, DC, Provincetown, and other New England venues. More…
Peter MacDonnell – Class of 1978
Born and raised in Winchester, Peter MacDonnell, class of 1978, is chief of the Winchester Police Department. Although he lives in Reading with his wife, he still considers Winchester home and remains passionate about the Winchester community. His oldest son serves in the US Marine Corp, and his youngest is a sophomore in college studying electrical engineering. They are his greatest pride. More…
Meghan Doyle Wilkinson – Class of 2005
Meghan Doyle Wilkinson is in the process of launching her women’s clothing brand, Tallulah & Poppy. Meghan is living in Acton, MA with her husband Drew, 17-month-old daughter Ella, and dog Sadie. She is finding ways to balance her move to a new home, being a new mom, and working on the February launch of her clothing brand. More…


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 Erik Johnson, Class of 1982
For the past 25 years, Erik has been the Migrant Farmworker Law Unit Director at Idaho Legal Aid Services in Nampa, Idaho.  Erik recently settled a case in federal court for a Basque ranch hand who was owed a huge sum of wages going back 8.5 years in a peonage type situation.  The terms of the settlement are confidential, but he shared that the worker did receive all he was owed and a bit more in damages. It was a complex case involving multiple causes of action, and took a year and a half to litigate.   More…..
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 Justin Serpone – Class of 1997
Justin Serpone is in his 12th season as head men’s soccer coach at Amherst College. Additionally, he is the director of Amherst LEADS, a leadership development program at Amherst College. He currently lives in Hadley, Massachusetts with his wife Angela and their three children (Lily, Tyson, and Annabelle). He is in the process of completing his fifth and sixth graduate degrees.  Justin has been back to Winchester High School a number of times over the years to work with Sachems Lead, the Amherst LEADS inspired program at WHS. Amherst LEADS has held events at WHS as well as having their staff run the annual Sachems Lead summer workshop to help develop WHS student leaders over the last four years. More….