Orange County, Virginia is your Holiday Headquarters!

With the holidays right around the corner, it’s time to indulge in seasonal wines and holiday feasts, get in the holiday spirit with a special event or finish your shopping in style! The Towns of Orange and Gordonsville transform into old-fashioned holiday villages, historical sites and homes are adorned and brimming with vintage 19th century holiday customs, and our local shops and markets offer festivities all month long. December offers many holiday events and special experiences to enjoy the festive season in Orange  County, Virginia.

main street with holiday lights
Photo Credit: Love Orange Virginia

James Madison’s Montpelier, Holiday Food Drive

James Madison’s Montpelier invites you to a free community holiday event, in a gesture of thanks for the ongoing support of our neighbors and friends.   Give back this Holiday Season by participating in James Madison’s Montpelier’s Holiday Food Drive for Love Outreach Food Pantry. They are accepting donations of non-perishable food to support the Food Pantry as they serve a community of families and individuals this Holiday Season. Donations can be dropped off Thursdays-Mondays, 9 AM – 4:00 PM at the David M. Rubenstein Visitor Center.

Take a Guided “Highlights of Montpelier” Tour or  Tour the grounds during the holidays at James Madison’s Montpelier. Montpelier offers a guided tour during select times Thursday-Monday. Guests will visit significant outdoor locations located in the historic core of the site, as well as three select rooms in the Madisons’ home.

Photo Credit: Montpelier Foundation

The Market at Grelen, Holiday Headquarters

Make the Market at Grelen your Holiday headquarters! Santa will be visiting every Saturday through the holiday season from 11 am – 2 pm. Visiting with Santa is FREE! Cut-Your-Own Christmas Trees will be available every Friday, Saturday, and Sunday from 10-3pm. Enjoy the magic of driving through the nursery and finding that special tree in Grelen’s Christmas Tree Field.  Don’t miss their Fraser Firs, Greens, Wreaths, Christmas trees and gifts galore. Enjoy the cozy greenhouse café seating after a full day of shopping!

Photo Credit: The Market at Grelen

2022 Annual Gingerbread House Contest

2022 Annual Gingerbread House contest returns in partnership with The Arts Center In Orange and Orange County Parks & Rec! Gingerbread houses will be displayed for viewing and voting beginning on Saturday, December 3 through December 17th!  Gingerbread structures will be displayed at The Arts Center in Orange! Cast your vote for the best gingerbread house while checking out local businesses on main street! Winners will be announced on or about Dec. 22.

Downtown Orange, Central Virginia’s Holiday Village, Saturday, Dec. 3rd

Join the ODA and several local organizations sponsoring activities December 3rd, from 12pm-4pm for this year’s holiday festivities! Vote on local business window decorations, enjoy good food and live music, visit Santa, and watch the parade!

Orange Rotary Club Parade, Saturday, December 3rd 4:30 pm

Join the Rotary Club  for the Christmas Parade in downtown Orange, Saturday, Dec. 3  at 4:30 pm. After the parade there will be a Christmas Tree Lighting Service in Taylor Park, Town of Orange.


Downtown Gordonsville, All Decked Out for the Holidays

Downtown Gordonsville is glowing this holiday season! Not only is Main Street sparkling so are the local shops with special one of a kind and locally made gifts for all tastes. Plenty of restaurants to stop in and have a wonderful meal!

Gordonsville Holidays on Main Street 

December 10th, 11 pm – 4 pm. Celebrate with us and join us for Old Fashioned Carriage Rides • Visits with Santa • Carolers • Live Music • Holiday Market • Local Performances • Cider & Hot Chocolate • Shopping along Main Street & Merchant Events

Barboursville Vineyard, Holiday Feasts

Join Barboursville Vineyard and Palladio Restaurant for their holiday feasts and special celebrations. The Octagon, a spectacular feast of four courses paired with a rare flight of four distinct vintages of Octagon, their Christmas Lunch Celebration and the New Year’s Eve Dinner and Celebration.

Photo Credit-Barboursville Vineyards

Liberty Mills Farm, Home for the Holidays

Home for the Holidays at Liberty Mills Farm! Saturday, Dec.10 & Sunday Dec. 11 enjoy scheduled photo sessions with Santa, hot chocolate, hay wagon rides and cookie decorating and crafts for all ages, plus shop the Farm Market and other area local vendors in an outdoor venue.
Firefly on the Fly – Dec. 10
Burnt Ends BBQ – Dec. 11

Get Tickets here! 

LOVE works Sculpture
Photo Credit: Liberty Mills Farm

Orange County Tacky Lights Tour

The Annual Tacky Lights tour returns this year! Grab some family or friends and enjoy cruising around looking at all the participating lit up houses on this tour! Please note that this is NOT A CONTEST, it is a light-hearted driving tour just for fun.

The viewing period will run Dec. 12th-31st.

The holiday season in Orange County brings a special time for the community to enjoy local traditions and small town charms. Come for the events, stay for the warm welcomes and cozy destinations—there’s no shortage of ways to enjoy the holidays. The events listed here are only the beginning, visit our events page for even more great holiday activities!

Looking for a cozy spot to call home for the weekend?  Check out our award winning Inns, Resorts, and Bed and Breakfasts on our STAY page.