School Traditions

With more than a 60-year history, Oakland honors several long-standing traditions that are an important part of the Oakland experience for both staff and students.

Oakland School's winter school takes place from September to May.
One of the Oakland School students and his grandparents celebrating Grandparent's Day.
An Oakland School student and her horse companion are ready for Horse Holiday.

Fall and Winter

Winter School

Because students also attend Oakland for five weeks each summer, we call the regular school year, from September to May, Winter School. Students get time off for Thanksgiving recess, winter holiday, and spring vacation and enjoy five to six weeks off before and after Summer Camp.

Fall Parent Day

During this happy event each fall, Oakland invites parents to campus to share time in the classroom, explore our grounds, and meet our faculty. Children are excited to share their Oakland experience with their families.

Grandparents’ Day

Visitors from around the globe join us each October for Grandparents’ Day, where grandparents partake in tours of the grounds and a delicious meal prepared from the Oakland kitchen. Photos of each visiting family serve as cherished memories of this special day.

Thanksgiving Gathering

Students and staff gather at the historic Union Mills Church next to campus to celebrate our blessings. The ceremony offers a point of reflection and the opportunity to express all for which we are thankful.

Horse Holiday

An Oakland tradition for decades, Horse Holiday honors our equine friends each December for their work and dedication to the school. Dressed in festive holiday attire, horses and riders parade from the barn to the playing field where a holiday tree adorned with carrots and apples awaits.


Valentine’s Day Lunch

Oakland students demonstrate love for their parents with a special lunch on Valentine’s Day. A memorable experience for all, the lunch celebrates the one-of-a-kind connection between parents and children.

Caught Being Good

During the entire month of March, when students traditionally need a little pick-me-up, Oakland faculty and staff distribute tickets to students when they are caught being good. Children save tickets to buy items in our CBG Store such as toys, jewelry, games, models, and more. The most prized purchases, though, are the special on- and off-grounds activities offered by staff members.

Oakland School makes sure to keep kids engaged throughout the school year.
Camper rings Oakland's cherished bell.
Oakland's campers gather together for a photo with popsicles in hand.


Movies Under the Stars

Every Friday night during camp, summer boarders gather on the tennis courts with their sleeping bags to enjoy a family-friendly movie in the great outdoors.

Our Bell and Flag

Following tradition from the last 60 years, we ring our old-fashioned bell between classes and gather around the flagpole each morning.

The No-Talent Show

On the day before mid-summer break, our staff puts on a variety of acts for the students, showcasing their various “talents” in this fun and light-hearted show.


At the end of camp, students deemed ready to transition out of Oakland are each honored by an individual speech from a teacher of his or her choice. This rewarding and emotional ceremony signals an important milestone in a student’s academic journey, serving also as inspiration for current students and families.


Recognition Banquets

Both the regular school year and summer camp conclude with a special recognition banquet where students are acknowledged for their academic and social achievements.

Star List

Recognition is central to The Oakland Way, which is why we use our weekly Star List to recognize top achieving students.

Concepts Performances

Performed with pride, each class presents what they have learned at the end of every Concepts unit. Students’ showcase their skills through dramatic and musical performances, science experiments, social studies presentations, art projects, and more. The shows highlight the joy of our students and is especially rewarding for everyone who helped these amazing children shine.


Since our founding, Oakland has believed in strong, open communication between parents and the school. Now published via a weekly email, our Friday News shares a review of the week as well as announcements, upcoming events at Oakland and in the Charlottesville area, and next week’s dining menu.

Community Service

Giving back has been an important part of Oakland’s history since our founding. Today, students of all ages learn about the challenges of our neighbors, both locally and abroad, as part of their curriculum, and the entire school comes together for both on- and off-campus service projects throughout the year.

Recognizing students' achievements throughout the year encourages students to keep working hard.
Oakland School students ready for a field trip.
Studies show students who give back to the community perform better in school.