Insider Logo


If you are looking for a fun and beautiful getaway for the holidays, then look no further than Charlottesville, VA. The shopping is phenomenal. The events are spectacular. And the decorations rival any big city. Join us for any or all of these events this season: (photo above courtesy of Rob Garland Photography)

Special Shopping

Martha’s Market – November 15-17 at Boar’s Head Pavilion

This annual event brings together craftspeople and artisans from near and far, giving you a chance to shop for all of your Christmas gifts in one place while supporting a great cause, women’s healthcare programs at Martha Jefferson hospital.


2022 Barrack's Road Holiday Parade - December 3rd.


Events at Wineries, Breweries, and Cideries

Veritas Illuminated

A spectacular 1/4 mile walk through the enchanting woods and vineyard at Veritas Vineyards and Winery illuminated by twinkling holiday lights and decorations.
The trail is open on select Thursday, Friday, Saturday, and Sunday nights.November 17, 2022 -- January 8, 2023 (visit their website for full dates and availability)5:15 PM to 8:30 PMVeritas Vineyards and Winery
151 Veritas Lane
Afton, VA 22920
Adults: $15.00 Ticket price for adults includes a limited edition souvenir logo glass, while supplies last.
Children ages 4-13: $10.00

Events at Historic Sites


The Oratorio Society of Virginia Presents: Christmas at The Paramount
Join Music Director Michael Slon and 80 of our community’s finest singers for this beloved Charlottesville holiday tradition. This year’s concert will feature the first cantata from Bach’s Christmas Oratorio with guest soloists and orchestra, as well as traditional favorites and arrangements of holiday classics such as Joy to the World and O Holy Night, among others. December 17, 2022 2:30 PM & 7:30 PMThe Paramount Theater
215 E. Main Street
Charlottesville, VA 22902
Admission: $10.00; $29.00; $36.00; $54.00

Cville Band-- Brass Quintet Christmas Performance
Join Hazy Mountain Vineyards & Brewery for a special performance in their Tasting Room as The Cville Band’s Brass Quintet performs all of your Christmas favorites to get you in the holiday spirit.
December 18, 2022
1:00 PM to 2:00 PM
Hazy Mountain Vineyards & Brewery
240 Hazy Mountain Ln.Afton, VA 22920
Admission: FREE

Other Fun Events

Boar's Head Winter Wander

Holiday City Market

Special holiday editions of the City Market every Saturday through December 17th. Shop handcrafted items from a wide variety of artisans, home décor, kitchen utensils, jewelry, textiles, and more. Additionally there will be a great selection of produce, meats, and other groceries. Saturdays November 26, 2022 - December 17, 2022
8:00 AM to 1:00 PM
100 Water Street
Charlottesville, VA 22902Admission: FREE

Brunch with Santa at Restoration
Enjoy our delicious brunch menu while kids visit with Santa, and the whole family enjoys the festive atmosphere. Reservations highly suggested.
December 17, 2022
11:00 AM to 3:00 PM
Restoration Restaurant
5494 Golf Drive
Crozet, VA 22932
Admission: FREE

Gingerbread House Making Contest
Join Hardware Hills Winery for their 1st Gingerbread House contest! Doors open at 12:00 PM to enjoy wine, sangria, mulled wine and food before the contest which begins promptly at 1:00 PM. Tickets include everything needed to create a gingerbread house, and feel free to bring additional items to make your house stand out. Prizes will be awarded for 1st, 2nd and 3rd place. Good luck!
December 18, 202212:00 PM to 4:00 PM
Hardware Hills Winery
5199 W River Rd
Scottsville, VA 24590
Tickets: $25

And if you are coming into town for any of these events, find great places to stay on our Where to Stay page.

Know of a holiday event that we missed? Leave it in the comments to share with everyone!