Hilton Head Preparatory School is kicking off the holiday spirit by hosting its annual Festival of Trees at the Hilton Beachfront Resort in Palmetto Dunes November 20 through December 5. The event is free and open to the public for perusing and shopping with trees, wreaths, and holiday décor items available for sale.
The event invites local businesses and community members to get crafty and creative. “Festival of Trees is special because it has truly become a Hilton Head holiday tradition,” said Margot Brown, Hilton Head Prep’s chief advancement officer. “For more than 40 years, it has brought together our school and the broader community at the start of the holiday season.”
During the two-week festival, the Hilton’s lobby will be overflowing with sparkling trees and merry wreaths. “There is something magical about walking into a space filled with more than 150 beautifully decorated trees, wreaths, and holiday displays,” Brown said. “I want people to slow down, wander through, notice the details, pick their favorites, and enjoy being together.”
An important component of the festival is that all proceeds benefit Hilton Head Prep’s tuition assistance program. “This is really the most important part of Festival of Trees,” Brown said. “We want Hilton Head Prep to be accessible to talented students and wonderful families who would benefit from a Prep education but may not be able to afford the full cost of tuition. Tuition assistance helps us open that door. The holiday spirit is ultimately about generosity, and I think supporting tuition assistance is a wonderful expression of that.”
Even though Hilton Head Prep has been hosting this holiday event for more than 40 years, each year’s offerings are diverse and fresh. “That variety is what makes the festival so much fun. You aren’t simply walking through a display of Christmas trees; you’re seeing all these wonderfully different interpretations of the holidays, and every year is completely different,” Brown said.
Hundreds of festive trees line the Hilton’s lobby.
Holiday spirit isn’t the only spirit on display at the event because some tree designers also bring their competitive spirit. With annual bragging rights on the line, shoppers can expect high-quality themed trees. “Our designers love the competition, and visitors have just as much fun picking out their own favorites,” Brown said. “I think that little bit of friendly competition also inspires everyone to get more creative every year.”
Prep families get involved with the fundraising event with each class collaborating to craft and create a tree based off of that year’s grade level theme. For 2026, the theme is Holiday Children’s Books. Popular book options include the Polar Express, The Night Before Christmas, and How the Grinch Stole Christmas. Visitors can expect to see a lot of creativity woven into this year’s theme.
To pull off such a large festival takes an extraordinary amount of planning from school staff, community participants, and volunteers. “It is a tremendous undertaking, and what people see when they walk into the festival is really the culmination of months of work,” Brown said. “Planning begins well before November with a dedicated committee recruiting designers and sponsors, coordinating the trees and displays, communicating with participants, organizing volunteers, and handling all of the logistics.”
Local businesses donate and decorate for the event.
Once the preparations and planning are in place, the decor starts arriving by the truckload at the Hilton. “There is the enormous job of getting everything into the hotel and transforming the space in a very short period of time,” she said.
Once the festival is set up and ready for viewing, Prep students and their families volunteer daily to assist shoppers. Then, as the event wraps up, a large team of volunteers is tasked with removing all the decorations and working through the logistics of allowing shoppers to pick up their purchases. “It takes a lot of people giving a lot of hours,” Brown said. “That’s another thing that makes the event special – it really is a community effort.”
Visit hhprep.org/giving/festival-of-trees for more information or to donate to the tuition assistance program.
Wreaths are also available for sale.