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…
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…
Campus Tours on Friday Afternoon
See The Winchendon School through your student’s eyes! Join a guided tour of campus led a Green Key Ambassador and get…
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!
Campaign ends Sunday, October 4th, 2026, 5:59 pm EDT
About
Join us on October 2-4 at The Winchendon School’s Fall Family Weekend!
Come home to Winchendon! Family Weekend is a chance to experience campus life, spend time with your student, meet their teachers and friends, cheer on the Wapiti, and reconnect with the community that makes Winchendon so special.
This year’s Family Weekend is especially meaningful as we celebrate 100 years of Winchendon graduates. From an all school community meeting and a conversation about Winchendon at 100 to family meals, faculty conferences, college counseling, fall athletics, a clam bake, trivia night, and our beloved Green vs. White whiffle ball game, there will be plenty of opportunities to make memories together.
Guests will enjoy a full schedule of festive and meaningful activities throughout the weekend! Be sure to check out the schedule and register for all of our special events here on campus.
The following opportunities will also be available if you’re looking to supplement your schedule even further but do not require registration.
- Centennial Exhibit, Marr Library: Explore the Centennial Exhibit showcasing photos, memorabilia, and stories from Winchendon’s history. Interactive displays and QR codes will allow guests to learn more and contribute to the school’s legacy of giving.
- Golf at the Gardner Municipal Course: Reserve a tee time and enjoy a round of golf with fellow parents and friends. Reach out to [email protected] for more information.
- Mount Monadnock & Mount Wachusett Hikes: Relive Mountain Day, a Winchendon tradition since 1965. Enjoy the natural beauty of New England with self-guided hikes at nearby trails.
- Tennis and Pickleball: Get ready to swing, serve, and socialize! Grab some friends and head over to the Ladeau Tennis Courts. Whether you’re a seasoned player or just looking to have fun on the court, this is a great way to enjoy our campus. Don’t forget your racket!
- School Store: Shop all of your favorite Wapiti Swag all weekend long.
- Fall Festival at Wildwood Farm in Westminser
- Oktoberfest at Wachusett Mountain