Special Events


Throughout the academic year, Highland School hosts special events, run by dedicated volunteers and staff, to bring our community together while raising funds and awareness for a range of programs and activities.

Highland Classic Golf Tournament
Friday, October 20, 2023

The annual Highland Classic golf tournament is a much-anticipated social event for parents, grandparents, alumni and alumni parents. Our Highland Heroes receive special recognition along with their foursomes, as do other generous sponsors. The 18-hole tournament is a scramble format, with food and beverages provided throughout the morning followed by an awards ceremony and announcements of raffle winners. Prizes for closest to the pin, longest drive, and putting contests are part of the fun, and offer creative sponsorship opportunities.  

Space is always limited so reserve your foursome and check out sponsorship opportunities now! Contact Briar Leake, Director of Special Events, at or call 540-878-2794.

The Andrew Winfree ’99 Memorial Scholarship Sporting Clays Event
Saturday, November 11, 2023

The Andrew Winfree ’99 Memorial Scholarship Sporting Clays Event is back by popular demand this year! The sporting clays competition benefits Highland School’s merit scholarship in Andrew Winfree’s name, typically drawing a large number of alumni who remember Drew as a talented multi-sport athlete, team leader, and proud member of the Highland School Community. Over the course of the day, participants compete in several sporting clays contests and enjoy each other’s company with complimentary lunch, drinks, and chances to win fun prizes! Proceeds from the event go toward the Andrew Winfree ’99 Memorial Scholarship, which is presented each year to a Highland student who demonstrates strong character and leadership. 
To sign up for the competition or get more information, contact Briar Leake, Director of Special Events, at or call 540-878-2794.

The Highland Auction
Saturday, April 20, 2024 

Our most-anticipated fundraising event of the year – the Highland Auction – is a festive evening offering fun, food and a fabulous array of 150+ items donated for spirited bidding. Every Highland family can join the party by contributing items, underwriting sponsorships, signing up for the volunteer Auction Committee, and recruiting friends and family to be your guests on on Auction night! 

Every item in the Auction is donated by parents, grandparents, faculty, alumni, local businesses and special friends. Costs are covered by ticket prices. So just like your donations to the Highland Annual Fund, every dollar you spend and every sponsorship contributed goes directly to meet the 10-15% difference between tuition income and the full cost to provide our robust educational program to your children.

Ready to join the fun on the Volunteer Auction Committee? No experience required - just a commitment to fun and friendship! Contact Briar Leake: or call 540-878-2794.
Every fall, watch your email for our annual kickoff announcement. Then bookmark our website and follow Highland Auction 2024 on Facebook and Instagram!

Grandparents Day
Friday, May 10, 2024

Each Spring, we invite the grandparents and families of Highland students to campus for a fun and inspiring morning event. Grandparents and families gather in the Upper School gym for a light breakfast and then our Lower and Middle School students and teachers take over. Students love to show off their school to their extended families and are proud to entertain them with songs and performances that highlight some of the things they've been working on throughout the year.

Afterward, grandparents and family members are invited to visit their student's classrooms and meet their teachers and friends. It's always great to see the power of home and school, two of the most important elements in a child’s life, working together to make great things possible for our students.

To learn more about Grandparents Day, please contact Briar Leake, Director of Special Events, at  or call 540-878-2794.


Highland School is a co-ed independent Pre-K2 to Grade 12 day school located in Warrenton, Virginia.