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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, James Madison’s Montpelier is adorned with vintage 19th century holiday customs and the Market at Grelen’s Enchanted Extravaganza features artisans in a beautiful Farm Market setting. November and December offer many holiday events and special experiences to enjoy the festive season in Orange County, Virginia.

James Madison’s Montpelier, Holiday Open House

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. Take a break from the holiday frenzy to relax and enjoy the season with a bit of history, tradition, and family-friendly activities. Free! Looking for some free fun during winter break…Kids are FREE at Montpelier from December 26th through January 1st!


The Market at Grelen, Holiday Headquarters

Wreath workshops, Enchanted Extravaganza, and lots of holiday fun all starts the day after Thanksgiving! Santa makes a visit EVERY Saturday through the holiday season. November 30th until December 21st.! Visiting with Santa is FREE! Don’t miss their Fairy Garden workshops, Christmas trees and The Enchanted Extravaganza, featuring holiday decor, handmade gifts from local artisans, Grelen trees and greens, and ready to hang wreaths.


3rd Annual Gingerbread House Contest

Cast your vote for your favorite Gingerbread creation at The Arts Center in Orange. Hosted by Orange County Parks and Recreation and the Arts Center In Orange. Come pick your favorite Gingerbread house created by local families and organizations. Voting will last from December 6-17th. Free! Open 10:00 am – 5:00 pm.


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! Sunday, December 8th will be a special holiday celebration downtown from 11:30 am – 3:30 pm. There will be live holiday music by solo artists and the award winning Orange County High School Band ensemble, fresh chestnuts roasted, Blue Ridge Cider Doughnuts, Orange School of Performing Arts performances, and a special visit from Santa at the historic Train Station. At 4:30 pm the Orange Christmas Parade hosted by the rotary will bring the cheer and directly after the parade there is a special memorial tree lighting at Taylor Park.


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, BBQ Exchange, Krecek Kakes for the your sweet tooth and check out the new additions to Main Street, Well Hung Vineyard Tasting Room and Restaurant Rochambeau.


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.


Ellwood Manor Victorian Christmas

Friends of Wilderness Battlefield will host the 11th annual: “A 19th Century Christmas at Ellwood Manor.” Children of all ages may visit with Santa and enjoy making period arts and crafts. After Santa departs at NOON, the house will remain open until 2:00 P.M., for guests who would like to enjoy the beautiful period decorations provided by the Fawn Lake Garden Club.


Christmas at the Exchange Hotel

Take time to wind down from the hustle and bustle of the holiday season. Tour the beautiful Exchange Hotel and Civil War Medical Museum, enjoy all the holiday trimmings of Christmas and meet the Grinch who will be making an appearance to take pictures with the children!


Orange County is simply stunning and the holiday season 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 in Orange County. The events listed here are only the beginning, visit our events page for even more great holiday activities!