main street with holiday lights
Photo Credit: Love Orange Virginia

When winter arrives, it’s time to indulge in local, seasonal wines, and holiday feasts. Towns of Orange and Gordonsville transform into old-fashioned holiday villages, historical sites and homes are adorned with vintage 19th century holiday customs and our local shops and markets offer festivities all month long in their beautiful farm market settings. December offers many holiday events and special experiences to enjoy the festive season in Orange  County, Virginia.

Photo Credit: Montpelier Foundation
James Madison desk
Photo Credit: Gene Runion

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 – 2:30 PM at the David M. Rubenstein Visitor Center. For more information, visit them online.

Take a Guided “Highlights of Montpelier” Tour or a Private House Tour during the holidays at James Madison’s Montpelier. Montpelier offers a guided hybrid 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.


The Market at Grelen, Holiday Headquarters

Santa and lots of holiday fun all starts the day after Thanksgiving! Santa makes a visit EVERY Saturday through the holiday season. Starting November 28th until December 19th.! 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. Make The Market at Grelen your Holiday Headquarters!

fresh holiday wreathes
Photo Credit-Grelen Facebook page

2021 Annual Gingerbread House Contest

2021 Annual Gingerbread House contest returns in partnership with The Arts Center In Orange, Orange County Parks & Rec, and Orange Downtown Alliance. Gingerbread houses will be displayed for viewing and voting beginning on Saturday, December 4, as part of Love Orange Virginia’s Gingerbread Walk and Downtown Orange Holiday Village! Free!  Gingerbread structures will be displayed in the windows of businesses along Main Street in Orange, VA. 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

Beginning on Black Friday and running through Christmas Eve, make Downtown Orange your holiday shopping and holiday cheer headquarters!

Holiday Village Gingerbread Walk, December 4th 10 am  – 4 pm

Part of the month-long Holiday Village — The Gingerbread Walk will take place on Saturday, December 4 from 10 am – 4 pm. Including the Gingerbread House Contest, coordinated by Orange County Parks and Recreation and The Arts Center in Orange, LIVE music, special family photo backdrops, a children’s Toyland walk-through activity, an array of holiday crafts presented by Paint it Orange in the Train Station, tours of the historic Orange County Courthouse, and Santa and his Orange Holiday Elves. Many shops will have special sales and events, and local churches have a great line-up of activities planned, too.

  • Join the Rotary Club  for the Christmas Parade in downtown Orange, Sunday, Dec.5  at 4:30 pm. Parade Theme: Christmas in America—How do you celebrate Christmas in America!
  • Christmas Tree Rededication Service approximately 6pm after the parade in
    Taylor Park, Town of Orange.


Photo Credit-Love Orange Virginia

logo for event


event flyer

Downtown Gordonsville, All Decked Out for the Holidays

Downtown Gordonsville is glowing this holiday season! Not only is Main Street glowing so are the local shops with special one of a kind and locally made gifts for all tastes. Local tastes you want to try while you are in the neighborhood, Patch Brewing Co., Krecek Kakes for the your sweet tooth and check out the newest addition to Main Street, Champion Icehouse.

Gordonsville Holiday Celebration & Market

December 11th, 12 pm – 5 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

LOVE works Sculpture
PC: Liberty Mills Farm

Liberty Mills Farm, Home for the Holidays

Home for the Holidays at Liberty Mills Farm! Saturday, Dec.11 & Sunday Dec. 12 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.
Philosopher’s Stone Pizza – Dec. 11
Burnt Ends BBQ – Dec. 12

Christmas Candlelight Tour at Exchange Hotel and Civil War Medical Museum

Saturday, December 11th, 5:00 pm – 7:00 pm. The Exchange Hotel is hosting a Christmas Candlelight Tour, experience the museum decorated in Victorian era Christmas decorations in candlelight along with museum curators dressed in period attire. Hot chocolate and Christmas sweets will be served. Entry fee will be a donation to the Museum.

Christmas Open House at Ellwood

Saturday, December 19th 1:00 pm – 4:00 pm. Friends of Wilderness Battlefield is pleased to welcome visitors to Ellwood to see the beautiful Victorian Christmas decorations prepared by the Fawn Lake Lawn and Garden Club. They will be open from noon to 3:00 PM Saturday, December 11 – Friday, December 17.



event flyer

ellwood manor house
Ellwood Manor

man and woman behind a microphone


It’s A Wonderful Life: A Live Radio Play, presented by Four County Players

This beloved American holiday classic comes to captivating life as a live 1940s radio broadcast, complete with live foley artists! With the help of an ensemble that brings a few dozen characters to the stage, the story of idealistic George Bailey unfolds as he considers ending his life one fateful Christmas Eve.

December 3, 4, 10, 11, 17, 18 at 8PM
December 5, 12, 19 at 2:30PM


Orange County Tacky Lights Tour

The 5th 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. 13th-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.