College Transitions

Serve as a College Liaison and mentor incoming freshmen from Winchester High School at your current college.

On June 7th, the Class of 2020 graduated from WHS.  As they head off to college, many will find the next year away from home especially daunting.  By becoming a College Transitions Liaison you can support them in their post high school journey while offering a welcoming and friendly face.

Join the program by clicking below.  You’ll need to answer 3 questions and then Save to be included in the list of Mentors.   Or email us your interest at

Sign up today as a college student liaison and help incoming WHS graduates find success!
Sign up today as an incoming Freshman to be paired with a WHS alum at your college.

Regardless of the college you attend or the degree you pursue, you remain a member of the Winchester and WHS community.

Until now there has never been one central place to connect with classmates. In response, a group of Alumni have launched the Winchester Alumni Association to connect our global community and celebrate Sachem success.   To date we have registered more than 1500 members, and are building programming around college transitions, professional networking, class and city gatherings, and the announcement of Sachem news and events.
Don’t forget to upload your resume, too. In 2020, we will begin posting summer job and internship opportunities and supporting professional networking programs. 

 Liaison Expectations

While every collegeliaison will personalize their approach to supporting incoming first year students based on their experiences and personality, the following are some suggested activities designed to create a similar experience for all of our Sachems in their first year at college.  The Alumni Association will strive to connect students /alumni by mid-summer after graduation.
Summer – Liaison will contact the first year student to congratulate them on their WHS graduation and make introductions.  They will share what year they expect to graduate, area of study, and any college team, fraternity/sorority, or club they associate with.  It is most helpful for both students to share contact information and how each best likes to be reached. Some Alumni have sent along t-shirts/car stickers for their colleges, but this is certainly not necessary.
Fall – In the first month after school starts, liaisons will be asked to check in with the new student.  First year students may be curious about class schedules, navigating roommate issues, local services, work study jobs, dining halls, or athletics.  Liaisons will take some time to make sure that they are acclimating to their new school.
Winter – The holiday season brings great cheer, but can also be a significantly stressful time for students.  A call or check in around exams from a liaison can be well-timed. Liaisons should take a moment to note how their freshman is doing socially, academically and emotionally. Anxiety and depression affect an increasing number of adults ages 18-22. A friendly face from home could make a huge difference and raise their spirits.
Spring Hopefully the rising second year student will have found their niche at school and is thriving and looking forward to their summer break.
Reach back and pay it forward!  First year students should help The Alumni Association build this effort by volunteering to serve as a liaison for the next class of incoming WHS graduates!
We thank you for your support of our young alumni and encourage you to share feedback and suggestions for this and all Winchester Alumni Association programs at