Do you know of a classmate or other 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 info@winchesteralumni.org.
Connect with past alumni spotlights at the Winchester Alumni Database.
Faculty/Staff
2010s
Danny Taliaferro, Class of 2010 – Danny Taliaferro, a member of Winchester High School’s class of 2010 has stayed local since graduating, building a business in wedding and event planning. He recently shared his thoughts on how his Winchester High School experience helped build resilience and put him on the path to where he is today. More
Marisa DeRosa, Class of 2012 – Marisa DeRosa is a local artist, nanny, and volleyball coach. Since graduating from Winchester High School in 2012, she has pursued her passion to work with kids as well as finding the time to start her own business: MD Designs. More…
James Anderson, Class of 2011 – James Anderson’s passion for running in high school has turned into his profession today. After graduating from Winchester High School, class of 2011, he continued his record-setting running career at University of New Hampshire. Once his collegiate track days were over, he has continued in the sport both personally running for a great cause (Team Rusty Rolls) and professionally as a college track coach. More…
Karen Li, Class of 2013 – Just a few weeks ago, Karen Li returned to Winchester High School to serve as the keynote speaker at the Sachems Lead summer leadership workshop for WHS Students on Aug. 21. Karen discussed her experiences while at WHS and beyond, which have helped shape the person she is today. More…
Jack Johansen, Class of 2016 – Jack Johansen knew early on that he wanted a hands-on career that would allow him to help people. He just didn’t know exactly what that was. As a junior at Winchester High School, he heard about the possibility of becoming an Emergency Medical Technician (EMT). He could save people’s lives by offering medical help. His path seemed clearer; he now had a direction. More
Lydia Mullan, Class of 2013 – A passion for sailing and writing led Winchester High School graduate Lydia Mullan, Class of 2013, to a dream job as associate editor with Sail Magazine, based in Salem, Massachusetts. More…
2000s
Emma Spencer, Class of 2008 – Emma Spencer, a 2008 Winchester High School alumna, counts running cross country and track among her happy memories of WHS. 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. . 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…
Bobby Bilicki, Class of 2001 – Bobby Bilicki took the lessons he learned from playing with some of Winchester’s legendary athletic coaches and applied them to his professional life. Now a successful accounts manager, he gives the same advice to current Winchester High School students that his coaches gave to him: Find your passion, work hard, and keep a positive attitude. More
JJ Bingel, Class of 2009 – JJ Bingel has taken lessons learned from Spanish and history classes at Winchester High School with him to Washington DC, Uruguay, and Argentina. JJ’s intellectual curiosity will next take him to Italy and eventually graduate school somewhere in Europe. More
David Seaver, Class of 2006 – A bike trip across country led David Seaver to find a second career and home in Colorado. More…
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…
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: nbc.com/ap-bio. The season premiere is Thursday, March 7, at 8:30 p.m. More…
Kaitlin Cey, Class of 2008 – Kaitlin McHugh Cey lives in Saskatoon, Saskatchewan Canada with her husband and three kids. We just welcomed our baby girl December 19 and other than trying to survive the cold Saskatchewan winters we are trying to survive three kids under the age of 3! More
David Peritz, Class of 2002 – An AP physics class taught Winchester High School graduate David Peritz, Class of 2002, the value of understanding scientific principles. Now, a cardiologist at Dartmouth Hitchcock Medical Center, Peritz has taken that lesson to heart. More
1990s
Arup De, Class of 1991 – I am an anesthesiologist, living in Delmar, New York. I take care of adults and children for elective and emergency or unanticipated operations or procedures that require moderate to deep sedation, regional anesthesia (like spinal or epidural anesthesia as well as nerve blocks for orthopedic anesthesia) or general anesthesia. I am also the president of the faculty practice and associate dean for clinical affairs of the Albany Medical Center. More…
Deanna (Della Cioppa) Colon, Class of 1991 Deanna (Della Cioppa) Colon graduated with the WHS Class of 1991 and is currently living in Simi Valley, California, where she cooks up talent and perseverance. More…
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…
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. More…
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 …
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. More….
Pete Gustin, Class of 1995 – Award-Winning Voice Actor in San Diego, CA
Chris Rucker, Class of 1993 – Marketing & Communications for Boston Cannons in Massachusetts
Kristine Leavitt Mullaney, Class of 1996 – Founder Residential Interior Design in Massachusetts
Stephanie Ciano, Class of 1991 – Founder Fromage Imports working Globally
1980s
Jeremy Curtin, Class of 1989 – Jeremy Curtin is our first alumni spotlight living overseas. Jeremy’s advice to current Winchester High School students is to take a chance, which has served him well since moving from the United States in 2003. Jeremy has worked and lived all over Europe. Now, he and his wife are raising their twin boys in Ireland. More…
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. More…
