The Winchendon School Fall Family Weekend 2026

Begin your Fall Family Weekend by checking in, picking up your name badge and welcome materials in Ford Hall Lobby anytime after 9:30. Be sure not to miss the opportunity to buy raffle tickets from members of our student government for a 50/50 drawing and other fun prizes!

Families are invited to join us as we officially kick off Family Weekend with a special all school community meeting. Come together with students, faculty, and families to celebrate the start of a wonderful weekend on campus. Space is limited since the entire school gathers for this event, so make sure to get there on time. Feel free to sit anywhere there is an open seat!

Stick around after Community Meeting and join Head of School Sean Duncan for a conversation about The Winchendon School at 100. Hear about Winchendon’s history, where we are today, and the vision for our next century. If your student has a G Block free, they are welcome to stay with you.

Nothing says fall like a BBQ! Join us on campus for good food and a laid back afternoon with the Winchendon community.

We use pickAtime to schedule parent and family conferences. Faculty will be available for conferences from 12:30 to 5:00 on Friday and 9:00 AM to 2:00 PM on Saturday.

To schedule your conferences, please visit pickAtime through the WIS Resource Board. You will be able to view each faculty member’s available times and select the appointments that work best for your family.

Please note that some faculty members will have athletic or co curricular commitments during these times, so their schedules may not show them as available for the entire conference period. We appreciate your understanding that our hardworking faculty and staff wear many hats, and we are grateful for their flexibility in making time to connect with families throughout the weekend!

Take a student-led tour of campus with one of our Green Key Ambassadors. Tours generally take about 30 minutes and are available all afternoon with sign-ups encouraged to ensure space. Tours will depart at 1:00, 2:00, 3:00, and 4:00.

Enjoy dinner in Faculty Hall with fellow families and members of the Winchendon community. The evening will feature live music from The Autumn Sunset Trio.

Immediately following dinner, parents and guardians are invited to Homewood for an adults only evening of cocktails, dessert, and conversation. Please note that current students are not invited; there will be programming for them on campus.

Begin your Fall Family Weekend by checking in, picking up your name badge and welcome materials in Ford Hall Lobby anytime after 8:30. Be sure not to miss the opportunity to buy raffle tickets from members of our student government for a 50/50 drawing and other fun prizes!

We use pickAtime to schedule parent and family conferences. Faculty will be available for conferences from 12:30 to 5:00 on Friday and 9:00 AM to 2:00 PM on Saturday.

To schedule your conferences, please visit pickAtime through the WIS Resource Board. You will be able to view each faculty member’s available times and select the appointments that work best for your family.

Please note that some faculty members will have athletic or co curricular commitments during these times, so their schedules may not show them as available for the entire conference period. We appreciate your understanding that our hardworking faculty and staff wear many hats, and we are grateful for their flexibility in making time to connect with families throughout the weekend!

Start your Saturday with brunch in the Dining Hall, offering a hot buffet and grab-and-go options to fuel your day of family festivities.

Whether college feels like it is years away or just around the corner, this is a self-guided fair designed to help families understand what lies ahead, ask questions, and begin thinking about the college search. Drop in when you’re free and move through the stations at your own pace.

Representatives from six colleges will be on hand to share insights and answer questions, giving families a chance to learn more about the admissions process directly from college professionals. We will also welcome Ben Sapovitz, founder of Studiously AI, who helped us launch Winchendon Connect, our new internal alumni network that allows both current students and alumni to connect, exchange ideas, and pursue career opportunities and mentorship from Winchendon alumni.

No matter where your student is in the process, come learn, listen, and start the conversation. There is no pressure to have all the answers. This is simply a chance to get familiar with the process and take the first step together.

Gather on the Quad for a classic New England clam bake. Enjoy great food, good company, and a beautiful fall evening on campus.

Put your family’s knowledge to the test at a lively night of trivia hosted by Keri Tremblay of Central MA Productions. Grab your team, bring your competitive spirit, and get ready to compete for special, exclusive prizes!

Start your Sunday with a casual two mile family fun run/walk around campus. All ages and abilities are welcome, so come get moving and enjoy some time together outdoors. Everyone who finishes gets a free t-shirt!

Join us for Sunday Brunch, featuring Chef Justin’s delicious omelette bar!

Join us as we celebrate the newest members of The Winchendon School’s National Honor Society. This special ceremony recognizes students who have demonstrated excellence in scholarship, leadership, service, and character, and celebrates their commitment to making a positive impact in our community.

Families of students being inducted will receive a separate invitation and additional details from Kayley Irvine ([email protected]).

Join us for a double header as the Girls’ 16U and 19U Hockey Teams take on the Northwest Generals. Bring your pom-poms and cheer them on:

16U Puck Drop at 3:20
19U Puck Drop at 4:50