Between the twinkling lights, festive decorations, and yuletide cheer taking over the town, it’s hard to miss the fact that the holidays are here once again. But what is easy to miss out on without taking a closer look? The dynamic lineup of events and attractions Charlottesville has on tap to help you get into the spirit like never before. From timeless ballets to dazzling light shows and beloved local gatherings, we’re here to make sure you don’t miss a minute of the season’s magic. Our gift to you? This 2025 guide to celebrating the holidays in and around Charlottesville — here’s to your best showing yet! 

1. Magic on the Mall (Downtown Charlottesville): As reliable as Old Saint Nick, the Downtown Mall turns into a glowing holiday scene every year with twinkling lights, festive shop windows, and hot cocoa stops at every corner. Stop by for the perfect mix of charm and cheer.

2. Grand Illumination (December 5th at Ting Pavilion): Introducing Charlottesville’s big kickoff to the holidays! Expect live music, food trucks, games, special guests, and the lighting of a massive tree that pulls the whole city together.

3. Winter Wander Trail of Lights at Boar’s Head Resort (November 14th – January 3rd): A glowing mile-long trail filled with light tunnels, lakeside reflections, and cozy fire pits. Equal parts peaceful and magical, this is a must-do tradition in the making.

4. Hooville Illumination (Valcrest Lane, Charlottesville): An over-the-top, music-synced neighborhood light show run by locals with serious holiday spirit. Tune your car radio and let the lights dance along.

5. Lighting of the Lawn (University of Virginia): On December 5th, faculty, students, and locals alike will gather on the Lawn for live performances, cocoa, and a synchronized light show that makes the historic Rotunda glow with festive energy.

6. Candlelight Christmas Tours at Monticello (Select dates in December): Step back in time with a visit to Jefferson’s mountaintop home, which glows with candlelight and greenery. If you’re in the mood for a quiet, elegant look at 18th-century holiday traditions, this is the stop for you.

7. Carter Mountain Orchard Thursday Evening Holiday Series (Thursday, December 4th, 11th, & 18th): Carter Mountain Orchard lights up Thursday evenings with its exclusive Holiday Series, turning the barn and grounds into a festive winter wonderland. Guests can shop for locally made gifts, sip complimentary hot apple cider, and enjoy live performances from local musicians. 

8. Charlottesville Holiday Market (Saturdays November 29th-December 20th): Charlottesville’s Holiday Market brings together local artisans downtown for the most joyful time of the year. Discover one-of-a-kind handmade treasures that make perfect gifts, and enjoy the season while browsing the best selection of unique creations.