At Cheshire Academy, personalized college counseling from year one is key.
In June, 111 students graduated from Cheshire Academy. The list of colleges they went off to was almost as long as their procession, including nearly 80 institutions from Ivies to “Big 10s” to international business heavyweights like Hult International Business School and IEU—Madrid.
When Cheshire Academy says it strives to find the ‘right-fit’ college for each student, it’s not just an enticing marketing slogan. College Counseling is one of the signature pillars of a Cheshire education, beginning in each student’s first year and continuing through graduation and beyond.
“We don’t start with a list of colleges. We start with the student,” said Madeleine Bergstrom P’29, CA’s director of College Counseling since 2015. “Our process is about understanding who each student is, what they hope to accomplish, and what environment will help them thrive.”
While any student can find a list of top colleges and universities in a quick Google search, Cheshires’s dedicated professionals help students discover institutions that truly fit their academic interests, learning style, personality, and goals.
When Cheshire Academy says it strives to find the ‘right-fit’ college for each student, it’s not just an enticing marketing slogan. College Counseling is one of the signature pillars of a Cheshire education, beginning in each student’s first year and continuing through graduation and beyond.
“The right match isn’t about prestige,” Bergstrom said. “It’s about finding the college where a student will be challenged, supported, and successful.”
Like most students, Nia Jackson ’26 came to campus not knowing much about the college application process.
“However, I did not feel worried or nervous because one of the first things the college counselors told us was, ‘There is a school right for you, and we just help you find it,’” Nia said.
Cheshire Academy college counselors work closely with each student and their family throughout the entire process. While many independent schools focus on admissions outcomes, the Academy takes the time to do the ‘matchmaking’ that better predicts long-term success.
Students explore a broad range of colleges and then narrow their list through conversations with their counselor and college reps who regularly visit Cheshire, campus tours, virtual sessions, research, and reflection.
They also have the advantage of Cheshire Academy’s annual College Fair, an established event that drew representatives from more than 135 colleges and post-graduate programs in spring 2026. For the first time ever, Cheshire Academy invited students from nearby Hamden Hall to attend, providing access to what has become one of the largest college fairs in Connecticut.
The Academy’s college counselors encourage their advisees to evaluate each college on more than its annual rankings. They look at academic programs, campus culture, location, size, financial fit, and extracurricular opportunities and meet with their advisors to build a list tailored to their goals. Most apply to 10 to 12 schools, including reach, target, and likely options.
College counselors meet regularly with admission representatives, attend professional conferences and maintain relationships across higher education to stay current with admission trends.
“Cheshire Academy’s college counselors bring years of admissions and college counseling experience, providing students with informed guidance and support throughout every stage of the college search and application process,” Bergstrom said. “We don’t have individual specialties, and that’s by design. We are all well versed in supporting all types of students – athletes, artists, actors, musicians, all of it.”
See Cheshire Academy’s Class of 2026 Matriculation List
Students here often build strong relationships with their college counselors. Nia said she relied on Bergstrom to give her honest, important advice.
“She was always available to revise my essays, help me determine my list of schools, and just give me so much support throughout the process,” Nia said. “And when I say always, I mean always. I could message at 11 p.m. or 5 a.m. and she would respond. She always knew what to say even if it was something I didn’t particularly want to hear, but needed to understand.”
Matias Candelo-Diaz ’26 said his college counselor, Laura Dempsey, helped him “in more ways than I can count.
“Through what feels like an infinite number of impromptu office run-ins, she helped me organize my application and show me what might be my best college fit from her knowledge,” Matias said. “She always checked in and was extremely thoughtful about how I felt about anything. My experience was nothing short of phenomenal.”
He heads to Connecticut College in the fall.
“When visiting my different options, what stuck out to me the most about Conn was the people I interacted with,” said the former cross–country runner and campus podcast host. “My feelings towards these people is evident in what I learned at CA about being a good community member, which I carried over when picking my school.”
Each year, seniors gather on May 1 to commemorate the traditional day to announce their college decision for the coming fall. Celebrate the Yes Day means proudly wearing hats, sweatshirts, and other merch from the next step on their journey.
By May 1, every 2026 senior and PG had at least one college option, with some having many to choose from, as they finalized plans for the fall. The long matriculation list showcased the wide variety of interests, educational goals, aspirations, and the true diversity of CA students.
Members of the Class of 2026 committed to such varied schools as Northeastern University, the US Air Force Academy, Georgia Institute of Technology, and UCLA. Many members of the Class of 2026 were recruited for athletics and committed to playing for college teams throughout the academic year.
Nia, a soccer tri-captain and prefect who earned a prestigious Yale School of Medicine summer internship in 2025, ultimately chose to attend the University of Connecticut, where she was accepted into a the Special Program in Medicine (SPiM), a BS/MD program that gives her a conditional acceptance to the university’s medical school. She earned a scholarship to attend and is in the honors program.
Nia said she was impressed to see how UCONN wanted to invest in her as both a student and a person, a positive attribute she said mirrored her Cheshire Academy experience.
“Besides the fact that UConn and Cheshire Academy have the same spirit colors,” Nia said, “I found a lot of similarities in the schools which is ultimately why this was the right decision for me.”
Bergstrom was pleased with Nia’s journey.
“We are always excited to see where our students choose to go after a long, thoughtful, application process,” she said. “We feel a little sad to see them go because we love getting to know them.
“But we’re mostly incredibly proud and thrilled at the myriad options our students have.”
Downloadable Guides
Explore our informational fact sheets to learn more about college counseling at Cheshire Academy.
