Insider Guide to Celebrating the Holidays in Charlottesville

Insider Guide to celebrating the holidays in Charlottesville, VA

The holiday season is upon us and there are so many ways to be jolly this time of year in Charlottesville! From sipping on Christmas spirits at special pop-up bars, to shopping for unique locally-made goods at holiday markets across the city, to channeling your creativity at various holiday workshops, there are an abundance of opportunities to #livelovelocal this time of year. We have rounded up ongoing festive events, one-time holiday highlights, along with a plethora of the holiday markets & workshops that will all help to make your season bright!

Ongoing Holiday Events & Pop-Ups

Jingle Bell Bar at Bobboo Spirits Bar at Quirk Hotel – Wednesday, Thursday, Sunday 5-10pm & Friday and Saturday 5-11pm through December 31st

The Case Study Chalet & Lounge at The Forum Hotel – Friday & Saturday 5-10pm, December 1 – February 29

The Matterhorn Alpine Ski-Bar atop Common House – open to members & non-members, Monday through Saturday 5-10pm through January 27th

Magic on the Mall brought to you by S.L. Williamson Company, Inc., Quirk Hotel and others – November 25th – December 31st.

  • Holly Trolley on the Downtown Mall – Saturday & Sunday, November 25th – December 23th 10am-2pm
  • Selfies with Santa on the Downtown Mall – Saturday, November 25th & December 16th 10am-2pm
  • Elves in Cville – pick up your North Pole Pass at Magpie Knits & Alakazam Toys or download the digital version.
  • Peppermint Trail – Follow the trail of peppermints on the sidewalks of Downtown Charlottesville to discover all sorts of treats featuring the favorite red and white candy. Download your brochure here in advance & stop into Petite Marie Bette, The Quirk Hotel & many more locations.
  • Best in Snow Windows – Your favorite downtown spots, including Magpie Knits, Agents in Style and Hedge Fine Blooms, are in a festive face off for the title of best holiday window decoration! Come down and vote for who you think has the jolliest windows.
  • Hanukkah CelebrationDecember 10th 

Boars Head Winter Wander – select nights, November 17th through January 6th 4:30-8:30pm. Prepurchase tickets here.

Veritas Illuminated – select nights, November 17th through January 6th 4:30-8:30pm. Prepurchase tickets here.

The Nutcracker performed by the Charlottesville Ballet – MLK Performing Arts Center, Saturday, December 2nd 11am & 3pm, Saturday, December 16th 11:30am & 3:30pm, Sunday, December 17th 12:30 & 4:30pm

Breakfast with Santa at Birch & Bloom at The Forum Hotel – Sunday, December 3rd, 10th & 17th 10am-2pm.

One Time Holiday Events

Holiday Open House at Brigid & Bess at the Dairy Market – Friday, December 1st 6-8pm

Charlottesville’s Grand Illumination at Ting Pavilion – Friday, December 1st 5-8pm

Lighting of the Lawn – Friday, December 1st 7-9:30pm

10th Annual Arc Piedmont Santa Fun Run/Walk at Ting Pavilion – Saturday, December 2nd 10-11am

Santa Paws Holiday Bazar Fundraiser at Castle Hill Cider – Saturday, December 2nd 9am – 3pm

Carriage House Christmas at King Family Vineyards – Sunday, December 3rd 10am-4pm

Holiday Open House at the Shops at Bellair Place – Saturday, December 9th 12-6pm featuring Be Just and the other fabulous shops in the Design Collective, stop by for festive libations, nibbles & holiday cheer!

Holiday Shop for a Cause at Derriere de Soie – 10% of sales go to Child Health Partnership, Saturday, December 9th 10am-5pm & Sunday, December 10th 12-4pm

Foxfield Balloon Glow featuring Monticello Country Ballooning, Thomas Jefferson Hot Air Ballooning & Blue Ridge Balloon Company – Wednesday, December 13th 2pm

Merrie Mill Farm & Vineyard Winter Solstice Gala & Dinner – Friday, December 15th 6-11pm. Purchase tickets here.

Christmas at The Dairy Market – Sunday, December 17th 12-4pm – get your tickets for Gingerbread House Decorating today Gingerbread house decorating starts at 12pm alongside free holiday activities including pictures with Santa, arts and crafts, and the third annual Toy Drive! Toy donations can be delivered to the Krissy Cakes food stall.

The Paramount Theater 7th Annual Brew& Buddy Run – Sunday, December 17th – run begins at 4pm, Elf screening begins at 6pm. Get tickets now.

Family Fun Night at King Family Vineyards – Wednesday, December 20th 4:30-7:30pm, Food Trucks from 4-7pm, Holiday Caroling at 5:30pm & Christmas Cartoons all evening.

Santa Specials at Agents in Style – Friday, December 22nd & Saturday, December 23rd, come shop for last minute gifts & holiday outfits and receive 15-50% off purchases.

Christmas Eve Heavy Hitter at pūrvelo – Sunday, December 24th 9:30am with Max & Robyn

Christmas Eve Bloody Mary Bar at Scarpa – Sunday, December 24th 10am-3pm

Christmas Eve Dinner at The Pink Grouse at Quirk – Sunday, December 24th

Christmas Dinner at Marigold by Jean Georges at Keswick Hall – Monday, December 25th 12-8pm. Reserve now.

New Year’s Eve Party at Quirk – Sunday, December 31st 9pm-1am. Ring in the new year at a chic NYE Bash at Quirk Hotel Charlottesville with a live band, dance floor, champagne toast, & more!

Holiday Markets

Charlottesville Holiday Market at City Market in the Water Street Lot- Saturdays 9am – 1pm through December 23rd

First Street Fair: Holiday Edition – Saturday, December 2nd 7am -12pm

Holiday Maker Market at Common House – Saturday, December 2nd 10am-3pm

Wine & Winter Market at Eastwood Farm & Winery – Saturday, December 2nd 12-5pm

Gordonsville on Main Holiday Market – Saturday, December 9th 10am-4pm – in addition the the fabulous vendor market there will be a dance performance (11am), Santa Visit (12-4pm) and Carriage Rides (2-5pm)

Crozet Holiday Market Crawl – Saturday, December 9th 10am-4pm

Sip & Shop Holiday Market at the Wool Factory – Saturday, December 9th 12-6pm & Sunday, December 10th 12-4pm

Holiday Market at the UVA Women’s Center – December 12th 1-5pm

Merrie Mill Farm & Vineyard’s 1st Annual Outdoor Holiday Market – Saturday, December 16th 11am-5pm

Holiday Classes & Workshops

Be Just Wreath Workshop at Fat Cat Farm – Saturday, December 2nd & Sunday, December 3rd 1-3pm

Holiday Wreath Workshop at Hedge Fine Blooms – Saturday, December 2nd & Saturday, December 9th 5-7pm

Wreath Making Workshop at Pippin Hill Farm & Vineyards – Tuesday, December 5th, Wednesday, December 6th & Thursday, December 7th 9:30am & 1pm

Wreath Making Workshop at Brigid & Bess at the Dairy Market with Aisling Flower Farm – Wednesday, December 6th 6-8pm

Wreath Workshops at Castle Hill Cider with Aisling Flower Farm – Saturday, December 9th & Saturday, December 16th 12-1pm

Holiday Card Watercolor Class in the Greenhouse at Pippin Hill Farm & Vineyard – Tuesday, December 12th 11am-1pm

Poinsettia Watercolor Class in the Greenhouse at Pippin Hill Farm & Vineyard – Wednesday, December 13th 11am-1pm

Holiday Canapés Cooking Class at Pippin Hill Farm & Vineyard – Wednesday, December 20th 6-9pm