Alumni Weekend
Single Hero
We look forward to hosting you and your family for a fun-filled weekend. Westchester is a closely bonded community that forges lasting connections among students, teachers and parents. Alumni Weekend offers you a time to reconnect with classmates, remember your Westchester experience, and celebrate the milestones together.
Milestone Class Years
Connect and Celebrate
Alumni Weekend 2026: May 8-9, 2026
Open to all alumni, join us as we honor milestone reunion classes and enjoy a variety of events that bring our Wildcat alumni community together. No matter when you graduated, there’s something for you—don’t miss this opportunity to celebrate the legacy and spirit of Westchester Country Day School!
Your registration for Alumni Weekend is free, but we do ask that you RSVP so we can prepare to welcome you. Some events, such as the W-Day 5K, have an additional registration fee.
Schedule of Events
Friday, May 8, 2026
Class of 1976 Celebration Dinner
6:30 p.m., Blue Water Grille, 126 E. State Ave., High Point
The Class of 1976 will be celebrating its 50th reunion in style at one of High Point's best restaurants.
Class of 1996 Celebration Dinner
6:00 p.m., String & SPlinter Club, 305 W High Ave., High Point
The Class of 1996 will be celebrating its 30-year reunion with families. RSVP to Holly Hekhuis Hill '96 at 336-259-8087.
Class of 2006 Celebration Dinner
Time and location TBA
The Class of 2006 is organizing a dinner in celebration of its 20th reunion in town. RSVP to Emily Finch Johnson '06 at EJohnson@rwbaird.com
Saturday, May 9, 2026
20th W-Day 5K "The Hobey" 5K + Fun Run
8:30 a.m.-11:00 a.m., Finch Center
Family-friendly! Be sure to warm up and stretch. Bring your whole family to run or walk the 5K, 1-Mile Fun Run, Little Cat Lap around the gym floor, or 50-Yard Diaper Dash! This event is held in memory of Hobey Ragan, devoted father of four Westchester alumni and dedicated Wildcat fan.
Additional registration is required for this event.
Varsity Baseball
1:00 p.m., Couch Baseball Complex
The Varsity Baseball team will host an opponent TBD at home in the NCISAA State Tournament. Admission is $10 for adults, students free.
Varsity Boys Tennis
3:00 p.m., Willow Creek Tennis
The Varsity Boys Tennis team will host an opponent TBD at home in the NCISAA State Tournament. Admission TBD.
Alumni Toast and Tours
5:00 p.m.-7:00 p.m., Wilson Student Center
Gather a group of all your classmates to come enjoy some hors d'oeuvres and beverages while receiving a tour of Westchester's campus. There may be guest appearances by some Westchester faculty!
Class of 2006 Drinks and Dinner
7:00 p.m., Otto and Blue, 1807 N Main Street, High Point
The Class of 2006 will continue its 20-year reunion. RSVP to Emily Finch Johnson '06 at EJohnson@rwbaird.com
Individual Class Parties
Times/Locations to be announced by classes
If you know of a gathering happening within your class, contact Susan Fagg.