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. December offers 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.   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, please visit   

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

Socially Distant 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 The Enchanted Extravaganza, featuring holiday decor, handmade gifts from local artisans, Grelen trees and greens, and ready to hang wreaths. Make The Market at Grelen your Holiday Headquarters!

PC: The Market at Grelen Facebook Page

4th Annual Gingerbread House Contest

4th Annual Gingerbread House contest returns in partnership with The Arts Center In Orange and the Orange Downtown Alliance. Voting will last from December 5-19th. Free! This year, 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. This event is sponsored by Krecek Kakes, LLC and Partners 1st Federal Credit Union.

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!

Join the Rotary Club in a special Facebook Live Virtual Memorial Tree Lighting ceremony! Beginning at 6pm Sunday, December 20th.

Holiday Village Gingerbread Walk, December 12th 12:30 pm – 6:30 pm

Holiday Village Gingerbread Walk: Browse Main Street from Byrd to Caroline on December 12th to view the entries in this year’s  “Gingerbread House Contest” that will be showcased in various storefronts.

Starting at 12:30 pm to 6:30 pm, see Santa in a no-contact, socially-distanced setting and let him know how nice you’ve been this year in spite of the COVID Grinch’s naughty behavior!  Shops will be open to welcome you — stop in to see what Santa’s helpers have been busy making, and what you can mark off your holiday gift list!

Taylor Park will be aglow with beautiful lights, and a delightful array of holiday-themed inflatables so you can capture the season’s joy with a holiday selfie!  Safety-wrapped candy canes and hygienically-packaged gingerbread men cookies will be offered to help lift your holiday spirits!  Join us in downtown Orange for a fun-filled, family-friendly, outdoor holiday experience!

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 addition to Main Street, Well Hung Vineyard Tasting Room.

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.

PC: Liberty Mills Farm Facebook Page

Liberty Mills Farm, Home for the Holidays

Home for the Holidays at Liberty Mills Farm will be December 12th and 13th! Scheduled photo sessions with Santa, hot chocolate, hay wagon rides and cookie decorating for all ages, plus shop the Farm Market and other area local vendors in an outdoor venue. Advance ticket sales start December 1st.

Christmas at the Exchange Hotel

Saturday, December 19th 1:00 pm – 4:00 pm. Join the Exchange Hotel in Gordonsville, Virginia for a family-fun filled Christmas celebration with light refreshments and appearances from some SPECIAL GUESTS!! Entry Fee is $5 a person (both child & adults). All proceeds go to the museum. Tickets must be purchased in advance.  Unfortunately no walk-ins allowed this year due to COVID-19.

Can’t make it to the open house? Come explore and tour during the holiday season to soak in the period decorations and history. Tour the beautiful Exchange Hotel and Civil War Medical Museum, enjoy all the holiday trimmings of Christmas.

Get your reservations now: Ghost Hunt With The Wraith Chasers At The Exchange Hotel Civil War Medical Museum

Sat, Feb 20, 2021, 7:00 PM – Sun, Feb 21, 2021, 12:00 AM

Tickets available HERE


Photo credit: Exchange Hotel Facebook Page


Orange County Tacky Lights Tour

The 4th 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. 12 through Dec. 31.


HOME FOR THE HOLIDAYS: A Four County Players Musical Revue

Oh, there’s no place like home for the holidays–-especially this year! Four County Players Community Theater is excited to bring audiences near and far the magic of a Four County Christmas and the charm of a classic holiday special to the comfort of your very own homes!

Professionally filmed on the Four County Players Mainstage with strict COVID-19 protocols, Home for the Holidays brings you the warmth and joy of the most wonderful time of the year through song, memories, and humor, all brought to life by some of your favorite local performers and special guests–-including The Jolly Old Elf himself! It’s perfect fun for the whole family!

Home for the Holidays: A Four County Players Musical Revue is available to stream on-demand from December 12, 2020 through January 3, 2021!

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.