The Winchendon School
Winchendon, MA
The Winchendon School Fall Family Weekend 2026
Date and time
Friday, October 2nd, 2026 –
Sunday, October 4th, 2026
Organizer
Friday Activities
Family BBQ on the Quad, 11:50-1:00
Join us on the Quad for a Welcome Family BBQ on Friday at 11:50 to kick off the start of the weekend! Come meet new…
Campus Tours on Friday Afternoon
See The Winchendon School through your student’s eyes! Join a tour of campus led by a Green Key Ambassador and get a…
Dinner and Live Music, 5:30-6:30
Enjoy Sage Dining’s finest in Faculty Hall, our beautiful dining hall! We’re thrilled to welcome longtime trustee, dear…
Cocktails and Dessert at Homewood, 6:30-8:30
Join Katherine and Sean Duncan at their home on campus for dessert and cocktails after dinner on Friday. This event is…
Saturday Activities
Brunch in the Dining Hall, 10:30-12:00
Start your Saturday with brunch in the Dining Hall, offering a hot buffet and grab-and-go options to fuel your day of…
Clam Bake on the Quad, 5:30-6:30
Gather on the Quad for a classic New England clam bake. Enjoy great food, good company, and a beautiful fall evening on…
Family Trivia Night, 7:00-9:00
Put your family’s knowledge to the test at a lively night of trivia hosted by Keri Tremblay of Central MA Productions…
Sunday Activities
All Weekend Long!
Family Fun Run Gold Sponsor
Present award(s) to winner(s) after the Run
Exclusive signage throughout the weekend, throughout all parts of…
Family Fun Run Silver Sponsor
Prominent signage at race
Full page ad placement in the Fall Famiily Weekend program
Recognition in all pre- and…
Family Fun Run Bronze Sponsor
Prominent signage at race
Full page ad placement in the Fall Famiily Weekend program
Recognition in all pre- and…
Family Fun Run Friend of TWS Sponsor
Prominent signage at race
Half page ad placement in the Fall Famiily Weekend program
Recognition in all pre- and…
Campaign ended Friday, October 2nd, 2026, 8:59 am EDT
Who is invited to Fall Family Weekend?
Fall Family Weekend is an opportunity for parents, guardians, grandparents, siblings, and other family members to visit campus, spend time with their student, and experience life at The Winchendon School.
Do I need to register?
Yes. Please register everyone who will be attending, including your Winchendon student. Registration helps us plan appropriately for meals, activities, and other weekend events.
Is there a cost to attend?
There is no cost to attend Fall Family Weekend.
How do I schedule conferences with my student's teachers?
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 to 2:00 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!
Where should I stay?
Families are welcome to stay at one of the hotels in the surrounding area. You can find recommendations at winchendon.org/visitors-guide. We recommend making reservations early, as availability can be limited during busy fall weekends.
Can my student stay off campus with us?
Yes. If your student will be staying off campus with your family during the weekend, please follow the usual weekend sign out procedures and communicate your plans with the appropriate residential life staff.
Can my student leave campus with family during the day?
Yes. Families may spend time off campus with their students during designated free periods. Please make sure your student follows the school’s sign out procedures before leaving campus.
What should I wear?
Fall Family Weekend is casual and comfortable. We recommend dressing for the weather and bringing layers. Some activities may take place outdoors, so comfortable shoes are a good idea.