What began as a festive stroll through twinkling lights has turned into something even more magical: love stories. Over its five-year run, the annual Winter Wander Trail of Lights at the Boar’s Head Resort has helped spark more than 25 engagements and become a cherished part of the Charlottesville holiday season. The event has also raised more than $50,000 for six local charities.
The event launched in 2021 with a simple goal, said Kevin Thurman, the Boar’s Head director of special events: Add something fun for Central Virginians during the holidays while drawing visitors to the region during what is typically a slower tourism season.
“The overall desire to bring Winter Wander to Charlottesville was to add to the collection of events in Charlottesville … a reason for people to come visit Central Virginia,” Thurman said.
That vision quickly exceeded expectations. Thurman still remembers opening night, the Friday after Thanksgiving in 2021.
Performers from the “Nutcracker in Lights” entertain visitors in the Enchantment District. The show is one of two new live performances this season, along with “Candy Cane Lane.” (Contributed photo)
“We were sold out that night, and we’d never done one of these before,” he said. “It was very much figuring out what was going to happen, how it was going to go and how it would be received.”
Each year since, organizers have expanded the experience, adding new scenes, more lights and live entertainment. In 2024, Winter Wander introduced a drone show that returns this season, with 200 drones lighting up the night sky Dec. 17 and 22, weather permitting. Two shows will take place each night at 6 and 8 p.m.
This year’s newest feature, the Glistening Grove, surrounds Firefly Pond with 700 luminaries standing 5½ feet tall, along with 200,000 pixels of light synchronized to music in a 15-minute show.
Winter Wander has also become a popular place to pop the question. More than 25 couples have gotten engaged along the trail. Thurman says every proposal so far has ended with a “yes.”
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