Special Events


Throughout the academic year, Highland School hosts several special events. These events, run by dedicated volunteers and staff, help to bring our community together while raising funds and awareness for a range of programs and activities.
Here's a brief summary of the most prominent events held each year including our annual Golf Tournament, Highland for the Holidays shopping event, the Highland Auction, and Grandparents Day.

Highland Classic Golf Tournament
2020 Date: TBD

Each Fall, Highland School hosts a golf tournament for members of the Highland community and their guests. Players group together in teams of four and then work together to try and post their best score over the 18 hole event. Special prizes are offered throughout the round for the team that gets closest to the pin or that hits the longest drive. Food and beverages are provided throughout the morning and then players gather for a great lunch after the round. Putting contests, prizes and raffles are also part of the day's events.

Tickets and sponsorships for the event are now available. For more information, please contact Briar Leake, Director of Special Events, at or call 540-878-2794.

Andrew Winfree '99 Sporting Clays Event
2020 Date: TBD

Join us for the third annual Andrew Winfree '99 Sporting Clays Event on Monday, November 11, 2019. This year we will go to the Shady Grove Hunting Preserve in Remington, VA. For more information on participating in or sponsoring this event, please contact Briar Leake, Director of Special Events, at or call 540-878-2794.

Highland for the Holidays 
2020 Date: TBD

Highland for the Holidays is a holiday favorite! Bring your family, friends, and neighbors, get all your holiday shopping done early, and support our school and local merchants.  Unique holiday gifts and decorations of all kinds, custom items made to order, an Opening Night party for adults, and food trucks all day Saturday and Sunday. One-stop fun for everyone and our generous merchants donate a share of all sales back to Highland School!

Then come back with the whole family – and invite your friends and neighbors – for two full days of shopping on a Saturday and Sunday in November. Our merchants will be open all afternoon. In the past, we’ve had photos with Santa and other fun for the kids, plus food trucks for lunch and a take-home dinner.

The Highland Auction
2021 Date: TBD

Our biggest social and fundraising event of the year is our annual Highland Auction. Each spring, the Upper School’s gymnasium is transformed into a theme-laced fantasy by a team of dedicated parents, staff, and faculty to set the stage for a beautiful and bountiful silent and live auction, complete with buffet dinner and dancing. It is a festive and fun evening in support of our school and our children, with underwriting sponsorships and generous donations – small and large – given by Highland families, staff, faculty, friends, and the business community. There is something for everyone, and everyone can go home a winner!

The importance of this event is indisputable, as it provides invaluable financial support for all aspects of our children's education, from faculty compensation to curriculum development, faculty training and fellowships, infrastructure maintenance and growth, technology initiatives, student scholarships, and financial aid, and more.  Its success is truly dependent upon the support of our community of families and friends, including the always-essential donations and underwriting sponsorships, but also extending to volunteering to help with event preparations, and, in true Hawk spirit – by attending this wonderful evening affair!

To learn more about how you can be involved in this year's Highland Auction, please contact Briar Leake, Director of Special Events, at or call 540-878-2794.

Grandparents Day
2021 Date: TBD

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, is what makes 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.