Holiday Activities and Events Going on in the Charlottesville Area.

We’re in the last mile of 2022—and you know what that means: it’s time to make merry with our loved ones. There’s nothing quite like the buzz of the holiday season. It’s a magical time that makes even the most Grinch-hearted among us feel enthusiastic about what’s ahead.

Ready to get into holly jolly spirit? To help you enjoy the most wonderful time of the year, we’ve rounded up some noteworthy holiday activities and events going on in the Charlottesville area.

1. Boar’s Head Resort Winter Wander Trail of Lights.

How do you feel about strolling in nature with a picturesque view of a lake and the Charlottesville rolling landscape? Sounds dreamy, right? Now add the illumination of fairy-like holiday lights to get an idea of what awaits you at the Winter Wander Trail of Lights.

The month-long event presented by the University of Virginia at Boar’s Head Resort promises to be an Instagram-worthy and memorable experience for the whole family. You can also book an overnight stay package for an elevated experience, including luxurious accommodations, an exclusive keepsake, and unlimited access to the Winter Wander trail of lights.

Where? 200 Ednam Drive, Charlottesville, Virginia 22903

When? December 10 to January 7, 2023

2. Charlottesville Holiday Market.

The Charlottesville Holiday Market is open! Drop by to stock up on holiday supplies to make the season celebrations seamless.

Get everything from quality produce to fresh groceries for hearty meals. You can also browse the wide selection of unique, handcrafted gift items on display—including textiles, jewelry, and home décor items.

Where? Charlottesville City Market – 100 Water St E, Charlottesville, VA 22902

When? Saturdays, November 26 – December 17, 2022

3. Monticello Holiday Evening Tours.

Thomas Jefferson’s Monticello is a deserved mainstay in nearly every Charlottesville travel or holiday itinerary. Tours of the “autobiographical masterpiece” are always a powerful and educational experience. But the Monticello is taking things up a notch this holiday season with rare evening tours.

Make reservations (434.984.9880) to take a peek at the Monticello when the sun sets and see how free and enslaved residents of the iconic home celebrated the holidays. Please keep in mind that dogs are not allowed (except certified service animals), and the tour is not accessible (steep stairs).

Where? Thomas Jefferson’s Monticello – 931 Thomas Jefferson Pkwy, Charlottesville, VA 22902

When? December 10 to December 30, 2022

4. Winter Solstice markets at IX Art Park.

The Farmers Market at Ix is marking the holiday season with ‘first of its kind’ Winter Solstice Evening markets. There are tons of holiday activities, festive lights, food vendors, and artisans to keep your entire family engaged.

Bask in the enthralling outdoor holiday atmosphere at the winter night market to kickstart your Christmas celebrations early.

Where? Ix Art Park – 522 2nd St SE, Charlottesville, VA 22902

When? December 21 and 22, 2022

5. Family Studio Day.

The Second Street Gallery is holding a free Family Studio Day on Saturday, December 17, on the 4th floor of Live Arts. It’s an opportunity to unleash your inner Picasso or just have fun playing around with free art materials and prompts.

The event features all kinds of hands-on printmaking activities to put you in a jolly mood for the festive season.

Where? Second Street Gallery, 115 2nd St, SE, Charlottesville, VA 22902

When? December 17, 2022

6. Selfies with Santa.

The legendary Santa Claus is arguably one of the most beloved holiday characters—and for a good reason. Who wouldn’t be fond of a jolly elf whose life purpose is to fly around in a reindeer-led sleigh and squeeze into chimneys just to bring joy to children (and adults)?

You’ll be glad to learn that Father Christmas is coming to town and will be dropping by the Downtown Mall. Bring the family to capture photos with Santa and create cherished memories.

Where? The Central Place, Historic Downtown Mall

When? Saturdays, November 26th – December 24th, 2022

7. Storytime at New Dominion.

If you’re a literature buff or simply someone who enjoys a good story, make a beeline for New Dominion Bookshop this holiday—and consider allowing your little book lovers to tag along. The bookshop holds weekly Storytime sessions covering a variety of books to capture the attention of people of all ages and tastes.

Where? New Dominion Bookshop – 404 E. Main St. Charlottesville, VA 22902

When? Every Saturday, December 17+, 2022

8. Veritas Illuminated.

The Veritas Vineyard and Winery invites you to a 1/4-mile walk through an illuminated path that takes you up and down its charming vineyards and woods.

Holiday lights and a scenic landscape aside, you can also excite your taste buds with a glass of wine, a mug of hot cocoa, or a hearty bite from their extensive menu of delicacies. Spark your holiday spirit with the Veritas Illuminated event.

Where? Veritas Vineyards and Winery – 151 Veritas Lane, Afton, VA 22920

When? December 15, December 24, December 25, December 31, and January 1

9. Magic on the Mall.

Something magical is brewing in Downtown Charlottesville this winter season—and everyone is welcome to experience it (free of charge). The Charlottesville Albemarle Convention & Visitors Bureau and Friends of Charlottesville Downtown are holding a bunch of events and activities to celebrate the holidays, including:

  • Elves in Cville: A magical scavenger hunt from November 26 to January 8.
  • Peppermint Trail: Find your favorite treats and candies by tracking peppermints on the sidewalks of Downtown Charlottesville from November 26 to January 8.
  • Holly Trolley: Enjoy Downtown Charlottesville atop the Jolly Holly Trolley from November 26 to December 24 (Saturdays and Sundays).
  • Live Performances: Drop by Downtown Charlottesville every Sunday from November 27 to December 18 to enjoy live musical performances.

Bottom line.

The holiday season is about cherishing special moments with loved ones. Try adding a few (or several) of these holiday events and activities going on in the Charlottesville area and watch memory-making moments roll in.

And as you embrace the holiday spirit, the team at Avenue Realty wishes you a happy festive season. Thank you for the great year!

Skip to toolbar