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The 99th Commencement Exercises and Other Celebrations: May 20-22, 2026

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About1Schedule5Attendees297Comments18
About1Schedule5Attendees297Comments18
Register now

Commencement Speaker Announcement! - 13 days ago

Dear Class of 2026,

We are thrilled and honored to welcome Bob Ritchie P ‘05 to be our Commencement Speaker at the 99th Commencement Exercises of The Winchendon School on May 22nd, 2026.

Bob and his wife, Donna, founded the Ritchie Hockey Foundation after the passing of their son, Jason, a Winchendon graduate. The organization leads skill clinics and awards scholarships to deserving student athletes who need financial assistance to participate in, and learn valuable life lessons through, sports. Since its inception in 2009, the Foundation has awarded over 80 scholarships and provided countless local children with free annual baseball and hockey clinics. Each year, the foundation selects one member of the senior class who embodies the values that Jason lived everyday to be the Ritchie Scholar here at Winchendon.

An insurance industry veteran with more than 35 years of experience, Bob Ritchie has built and transformed businesses ranging from startups to large national insurance companies. As the founder of American Integrity Insurance, he is committed to the success and growth of the company along with the stability of the insurance marketplace. Bob has been a driving force in securing meaningful property insurance reform in Florida. His advocacy helped bring about critical legal changes that address a crisis directly impacting insurance availability and rates for all Floridians.

Bob is a graduate of the University of Evansville. He graduated with a BS in Finance with a minor in music. He also serves on the board of Enterprise Florida, Inc. (EFI), the principal economic development organization for Florida.

Posted on Friday, April 3rd, 2026, 9:00 am EDT

About

In the days leading up to our graduation ceremony on Friday, there will be a slate of special events for seniors and postgraduates, including an alumni induction event at the WooSox game on Wednesday, May 20th and Senior Dinner on Thursday, May 21st.

Please read the schedule and registration options carefully and reach out to [email protected] with any questions!

Details

Date and time

Friday, May 22nd, 2026

10:00 am – 12:00 pm EDT

Location
The Winchendon School
172 Ash Street
Winchendon, MA 01475
View map

Details

Date and time

Friday, May 22nd, 2026

10:00 am – 12:00 pm EDT

Location
The Winchendon School
172 Ash Street
Winchendon, MA 01475
View map

Registration options

Alumni Induction Outing: Worcester Red Sox vs. Rochester Red Wings on Wednesday, May 20th at 4:00

All graduating seniors and postgraduates are invited to attend a special Alumni Induction Event at the WooSox game! Buses will depart The Winchendon School at 4:00 and return by 10:00. All students must take school transportation.

This event is required for all graduating students. Please register your student to confirm that they will be in attendance. If, for some reason, a day student cannot attend, please reach out to Katherine Duncan at [email protected].

Senior Dinner on Thursday, May 21st at 6:00 PM

Seniors, postgraduates, and two guests are invited to our awards ceremony and formal dinner in Faculty Hall. All graduating students are expected to be in formal attire, and their guests are encouraged to dress to impress!

Parent Reception at Homewood immediately following Senior Dinner on Thursday, May 21st

Immediately following Senior Dinner, parents and guardians are invited to join Sean and Katherine Duncan at their home on campus to toast the Class of 2026! Students will be invited to a different activity at this time.

99th Commencement Ceremony of The Winchendon School honoring the Class of 2026 on Friday, May 22nd at 10:00 AM

The Class of 2026 and up to eight of their guests are invited to the 99th Commencement Exercises of The Winchendon School. Please do not include your student in the total amount of attendees.

Coffee & pastry station will be available in Ford Hall beginning at 8:30 AM. Graduation seating opens at 9:30 AM. Commencement Exercises begin promptly at 10 AM.

All graduating students are expected to be in formal attire, and their guests are encouraged to dress to impress! Whether permitting, the ceremony is scheduled to be outdoors.

Graduation Brunch on Friday, May 22nd from 11:45 AM to 1:00 PM

Join us in the dining hall for a casual buffet brunch immediately following the graduation ceremony. If you plan on attending, please include your graduate in your total number of attendees.

Handicap Parking Pass

Complimentary

If you require a handicap parking pass for Thursday or Friday, please let us know by registering for one here. We will email you a pass that you can print at home and place on your dashboard. If you prefer, we’d be hapy to mail you a pass instead. Please contact [email protected].

General Parking will be in the lot at the Jason Ritchie ‘05 Ice Arena. More information regarding general parking will be shared as we get closer to the event.

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The Winchendon School
172 Ash St, Winchendon, MA 01475
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