Winter Family Weekend

We are pleased to welcome parents, grandparents, siblings, and friends to enjoy the Cushing experience at Winter Family Weekend.

2024 Winter Family Weekend

Our 2024 Winter Family Weekend was a great success. Families had the chance to meet with teachers and advisors, attend sporting events and performances, network with other Cushing families, and get a first-hand sense of the Cushing experience.

Here are some links to gallery images from the weekend:



2024 Weekend Highlights

  • Class visits. Sit in on abbreviated versions of your student’s classes on Friday to get a sense of academic life at Cushing. 
  • Meetings with teachers and advisors. Schedule appointments with the people at Cushing who work with your student every day. (Appointments will open to registered families about two weeks prior to February 23. Please note: college counseling appointments are for families of juniors only.)
  • Enjoy meals with students and faculty in our bustling dining commons.
  • Head of School Reception. Meet fellow parents at our art gallery Friday evening for an adults-only gathering.
  • Athletics. Cheer the Penguins on at their home matches!
  • Winter Musical. See Cushing's production of Pippin!
  • Art Show at the Emily Fisher Landau Center for the Visual Arts. Marvel at the talent of Cushing's student artists.

2024 Winter Family Weekend Schedule

Friday, February 23, 2024

  • 7:30 - 8:30 am — Breakfast for Students (Fisher-Watkins Dining Commons)
  • 8:00 am - 4:00 pm — Registration (Main Building)
    Continental breakfast and snacks will be available for parents in the Admissions Lounge
  • 8:30 am - 12:15 pm — Class Visitation (Various classrooms)
    There will be a modified academic schedule on Friday so you can join your student and attend a session of all of your student's classes. (Don't be fooled: you are encouraged to join your child. Many parents report classroom visitation as one of their favorite events of the weekend.)
  • 8:30 am - 12:00 noon — College Counseling Meetings (College Counseling Office, Main Building, 2nd Floor)
    Meeting times with College Counselors are reserved for juniors only.
  • 9:30 am-9:55 am Parent Assembly (JRC Theatre Room)
  • 11:00 am - 1:30 pm — Lunch (Fisher-Watkins Dining Commons)
  • 11:00 pm - 1:30 pm — Family Portraits (Fisher-Watkins Dining Commons Lobby)
  • 1:00 pm - 4:00 pm — Teacher/Advisor Meetings (Various Classrooms)
    10-minute meetings scheduled in advance of Winter Family Weekend
  • 4:30 - 6:00 pm — Head of School Reception and Art Show (Emily Fisher Landau Center for the Visual Arts/Maude Bowen Carter Gallery)
    All parents are invited to a parent reception at the Art Show hosted by Dr. Randy Bertin
  • 5:00 - 7:00 pm — Dinner (Fisher-Watkins Dining Commons)

Athletic + Performing Arts Events

  • 6:00 pm — RUST CUP: Boys' Varsity B Hockey vs. Winchendon School (Iorio Arena)
  • 7:30 pm — Winter Musical: Pippin (Cowell Chapel, Main Building)
  • 8:00 pm — Boys' Varsity Basketball vs. Wilbraham & Monson (Watkins Field House)

Saturday, February 24, 2024

  • 8:30 am - 12:00 noon — Registration (Main Building)
    Coffee and snacks will be available in the Admissions Lounge  
  • 9:00 am - 12:30 pm — Teacher/Advisor Meetings (Various Classrooms)
    10-minute meetings scheduled in advance of Winter Family Weekend
  • 9:00 am - 12:30 pm — College Counseling Meetings  (College Counseling Office, Main Building, 2nd Floor)
    Meeting times with College Counselors are reserved for juniors.
  • 10:00 am - 1:00 pm — Brunch (Fisher-Watkins Dining Commons) 
  • 1:00 pm - 2:30 pm — Teacher/Advisor Meetings (Various Classrooms)
    10-minute meetings scheduled in advance of Winter Family Weekend
  • 1:00 pm - 2:30 pm — College Counseling Meetings  (College Counseling Office, Main Building, 2nd Floor)
    Meeting times with College Counselors are reserved for juniors.

Athletic Events

  • 12:00 noon or 2:00 pm — RUST CUP: Boy's Varsity B vs TBD (Iorio Arena)
  • 2:00 pm — Boys' Prep Basketball vs. St. Andrews School (Watkins Field House)
  • 2:00 pm or 4:00 pm — Boys' Varsity Basketball vs TBD (Watkins Field House or Heslin Gymnasium)
  • 4:30 pm — Boys' Varsity Hockey vs. Governor's Academy (Iorio Arena)
  • 7:30 pm — Winter Musical: Pippin (Cowell Chapel, Main Building)

Please note: You may take your student off campus using our REACH system only after their last commitment (a game, practice, or activity) has concluded.

Monday February 26 is a “free” day with boarders returning by 7:30 pm.

On Friday of Winter Family Weekend (February 23), the earliest departure time from campus will be 12:15 pm as students are expected to attend all classes. Students who have games or performances will need to set their departure for the conclusion of their event. Students are not required to leave and many students do remain on campus. We ask that students do not get plane tickets any earlier than 3:00 pm on Friday. Students need to return on Monday (February 26) by 7:45pm check-in. There is no school transportation to/from airports around Winter Family Weekend. 

If you cannot make it for Winter Family Weekend and/or your student chooses to stay on campus we will be holding a full calendar of meals and events.

Frequently Asked Questions

Do I Have to Register to Attend?

Yes. If you are planning to attend Winter Family Weekend please register all family members that will attend so that we can provide name tags and plan for meals.

Can Grandparents and Siblings Attend?

Absolutely!  All family members are welcome.

How Do I Make Appointments With Teachers and Advisors?

You can schedule individual meetings with teachers and advisors. The system is called Pick-a-Time. To access Pick-a-Time please login to MyCushing and go to the RESOURCE board. You will see a yellow post-it note icon. If you are unable to attend or fit an appointment into your schedule you may email a teacher for a phone call or Zoom appointment after the weekend.

Can I Take My Student Off Campus?

Yes. A student can leave campus (after checking out properly using the REACH system) after their last commitment for the weekend. Students will not be excused from an athletic game or performance commitment. It is a long weekend. Boarding students return by Monday, February 26 at 7:30 pm.

Can Students Stay On Campus All Weekend?

Yes. Not all students have family attending and will be on campus. Dorms are open and supervised and meals and activities are planned.

What Is the Dress Code for Families?

Winter Family Weekend is all about comfort and showing your Penguin spirit by wearing Cushing garb or purple and white if you have it!! The dress code is casual, even for the reception. You will do a lot of walking around campus so please wear comfortable footwear.

Where Do I Park When I Arrive to Campus?

Parking will be available on School Street and Academy Street as well as the Iorio Arena and Watkins Fieldhouse parking lots. Please contact the Advancement Office if you have a family member with mobility issues and we can assist.

I’d Like to Make a Gift to the Cushing Annual Fund.  How Do I Do So?

You can make your gift online, by Venmo, or by sending a check payable to Cushing. Find additional information on our Giving Overview Page.



Making Plans

Lodging options in the area are extremely limited. We recommend that you book as soon as possible. Please see a list of options below as well as a list of places to eat in the area.


The Colonial Hotel
625 Betty Spring Road
Gardner, MA 01440
(6.5 miles)

Great Wolf Lodge
150 Great Wolf Drive
Fitchburg, MA 01420
(9 miles)

DoubleTree by Hilton Hotel
99 Erdman Way, 
Leominster, MA 01453
(14 miles)

Springhill Suites by Marriott – Devens Commons Center
27 Andrews Parkway
Devens, MA
(23 miles)

Inns and Bed and Breakfasts

The Maguire House
30 Cobb Rd.
Ashburnham, MA01430
(1.5 miles)

The Monadnock Inn
379 Main Street
Jaffrey, NH 03452
(20 miles)


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