Holiday Fun in Charlottesville
Written by Editor at Charlottesville Insider - October 30, 2025
Charlottesville, Virginia offers a vibrant lineup of fun holiday events near downtown from mid-November through December 31st, making it an ideal destination for families, couples, or anyone seeking seasonal cheer. From dazzling light displays to interactive scavenger hunts, markets, and festive performances, there’s something for everyone to enjoy.
Tree Lighting & Downtown Festivities
Downtown Charlottesville & Nearby 2025 Holiday Events
- Charlottesville Grand Illumination 2025
December 2025 | Downtown Charlottesville
Kick off the season with music, hot cocoa, and the tree lighting at Ting Pavilion—a family favorite tradition for 2025. - Magic on the Mall 2025
November 21, 2025–January 7, 2026 | Downtown Mall
Enjoy the Peppermint Trail, the Elves in Cville scavenger hunt, window displays, and recurring free activities for kids. - Charlottesville Holiday Market 2025
Saturdays, November 29–December 20, 2025 | Water St. Parking Lot
Shop handmade goods, local food, artisan gifts, and holiday treats at this open-air community market. - Charlottesville Waldorf School Holiday Bazaar 2025
December 5–6, 2025 | Charlottesville Waldorf School
Enjoy local crafts, music, performances, and children’s holiday activities.
Major Light Shows & Seasonal Experiences
- Winter Wander Trail of Lights 2025
November 14, 2025–January 3, 2026 | Boar’s Head Resort
Dazzling family light walk, featuring the 2025 debut of “Glistening Grove” and “Nutcracker in Lights” show at the Enchantment District. - Carter Mountain Orchard Thursday Evening Holiday Series 2025
December 4, 11, & 18, 2025 | Carter Mountain Orchard
Holiday evenings with music, cider, and seasonal cheer overlooking the city.
Live Performances & Shows for 2025
- Charlottesville Ballet’s The Nutcracker 2025
Select dates, December 6–22, 2025 | Martin Luther King Jr. Performing Arts Center
A classic holiday ballet with professional and student dancers. - Cirque Dreams Holidaze 2025
December 11, 2025, 7:30 PM | John Paul Jones Arena
Internationally renowned holiday circus spectacular for 2025. - The Oratorio Society of Virginia: Christmas at The Paramount 2025
December 2025 | The Paramount Theater
Choir and orchestra present carols and festive classics in a Charlottesville tradition.
Artisan Markets & Holiday Shopping for 2025
- Albemarle Farmers Market Holiday Market 2025
November 22 & December 13, 2025 | Forest Lakes South
Local produce, baked goods, handcrafted items for gifting. - Holiday Arts & Crafts Fair 2025
November 1, 2025 | The Center at Belvedere
Over 50 artisans with unique works in a festive community atmosphere. - Martha’s Market 2025
December 2025 | Various venues
Fundraiser market for breast cancer causes, featuring top artisans and specialty foods.
Signature Holiday Destinations in 2025
- The Market at Grelen 2025 Holiday Events
November & December 2025 | The Market at Grelen
Wreath workshops, botanical watercolor classes, holiday house tours, movie nights, and special greenhouse dinners—showcasing Grelen’s natural beauty throughout the 2025 season. - Trump Winery Holiday Market 2025
December 6, 2025 | Trump Winery Grand Hall
Food, crafts, wine, and local shopping for the 2025 holidays. - Chiles Family Orchards Holiday Pop-Up 2025
Saturdays, November 29–December 20, 2025 | Chiles Family Orchards
Cider, apples, donuts, and Virginia-made holiday treats. - Visit Monticello During the Holidays 2025
Throughout December 2025 | Monticello
Holiday house tours and wreath-making, echoing Jefferson’s 19th-century traditions.
