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As winter embraces Orange, Virginia, the county transforms into a festive haven, creating holiday joy for locals and visitors. Orange, surrounded by historical sites and a strong sense of community, welcomes you to enjoy the season’s enchantment through various captivating events and activities. 

Every part of Orange, from small marketplaces to historic buildings, will let you experience the festive atmosphere. Join me as we explore the delightful list of Things to Do in Orange, VA, for the Holidays—a county transformed into an artwork painted with the colors of joy, kindness, and holiday magic!

This post will be updated regularly as 2024 events are announced!

Best Things to Do in Orange County, VA, for the Holidays

Montpelier, VA

Montpelier Open House

Begin the holiday season with a historical tour of Montpelier, the home of the fourth president of the United States, President James Madison. The Montpelier Open House provides a one-of-a-kind opportunity to learn about this historic estate’s rich history. 

As you pass beautifully adorned chambers decked with seasonal magnificence, you will hear stories from the past resonating through the sacred hallways. The Madisons’ home will be decorated according to 19th-century customs, offering a glimpse into the festive traditions of the past.

Open house tours are available Thursday-Sunday from 9:00 am – 4:00 pm, and visitors may explore the historic residence. The David M. Rubenstein Visitor Center awaits, with exhibitions for cultural exploration and a Museum Shop for holiday shopping. For young enthusiasts, the Paint it Orange holiday crafting activity provides a creative touch to the festive atmosphere.

Check out tickets here.

Horse drawn carriage in Gordonsville, VA

Gordonsville on Main Holiday Market

Mark your calendar for December 14th, as Gordonsville on Main Holiday Market creates a winter wonderland across the town. From 10 a.m. to 4 p.m., Main Street transforms into a bustling winter marketplace, allowing you to take a festive journey through a carefully selected variety of gifts, crafts, and local treasures.

Immerse yourself in the festive atmosphere as you wander along Main Street. Merchants line the sidewalks, selling various unique and handcrafted items. From vibrant decor to locally crafted sweets, the market is a beautiful place to find that unique present for your loved ones.

As you explore, you can enjoy carriage rides, encounters with Santa, and other activities that add to the fun. Each seller has unique merchandise, providing a varied and enjoyable shopping experience. 

More details coming soon!

The Barn at 678 Vineyard Tasting Room entrance

Holiday Wine Express

Calling all wine enthusiasts! The Holiday Wine Express, available from December 1st to 24th, takes you on a lovely journey through Virginia’s picturesque vineyards. This festive adventure allows you to visit five participating vineyards: Honah Lee Vineyard, Reynard Florence Vineyard, The Barn at 678 Vineyard, Woodbrook Farm Vineyard, and Chestnut Oak Vineyard.

To participate in the Holiday Wine Express, get a ticket to sample the different and delicious wines at each vineyard. As you go on your wine-infused adventure, have your ticket stamped at each stop. This not only adds an enjoyable twist to your oenophilic trip, but also qualifies you for an exciting opportunity.

All completed tickets will be entered into a raffle on December 29th to win a Holiday Wine Express basket. The basket, filled with delectable delights from all five participating vineyards, highlights the region’s diverse wine and treat offerings. It’s an opportunity to savor the season’s flavors while perhaps bringing home a bounty of holiday delights.

St. Thomas Parish Church in Orange, VA

St. Thomas Parish Church

Escape the hectic holiday season and find serenity at St. Thomas Parish Church, a historic landmark symbolizing Orange’s enduring faith. This sacred space has exceptional architecture and radiates a feeling that serves as a peaceful break amidst the joyful chaos.

With its rich history and timeless architecture, the church offers more than simply a physical sanctuary. It provides a space for reflection and contemplation, allowing visitors to find serenity among the rush and bustle of the holiday season. St. Thomas Parish Church’s calm environment offers an atmosphere where one can pause, breathe, and enjoy Orange’s enduring spiritual legacy.

Check out their schedule for seasonal offerings.

three nutcrackers
[Not the actual Giant Nutcracker Head!] Photo by Alain Bonnardeaux on Unsplash

Giant Nutcracker Head

Embark on a fascinating journey down Blue Ridge Drive in Orange to witness the Giant Nutcracker Head, a holiday spectacle that captures the spirit of festivities. Standing tall and bold, this festive figure is more than simply a decoration; it’s an icon of joy that brings seasonal magic to Orange’s heart.

Whether you’re a local or a visitor exploring Orange’s attractions, the Giant Nutcracker Head is a delightful addition to the festive scene. It’s a symbol that captures the festive spirit, bringing smiles and kind wishes to all who encounter its unique beauty. 

Note: To find this enchanting spectacle, make sure to enter Blue Ridge Drive, not ROAD. Consider heading to Berry Hill Road and Blue Ridge Drive for the best route. While there may be no trespassing signs along the way, the visual delight of the Giant Nutcracker Head makes the detour worthwhile, offering a magical and festive experience.

Folking store in Gordonsville, VA

Main Street Shops in Gordonsville

Enjoy the season’s enchantment with a stroll along Main Street in Gordonsville as the town’s little shops become a festive paradise. Each boutique along this picturesque street is adorned with festive décor, adding to the town’s festive ambiance and tempting you to shop, dine, and indulge in the holiday fun.

As you wander past boutique stores and delightful cafés, you’ll be greeted by windows adorned with festive delight. The creativity and craftsmanship on each display represent a story about the town’s character, inviting you to discover Gordonsville’s unique offers. Check out local favorites such as Cavallo Gallery for unique gifts and Folking, a vintage clothing store.

Take your time browsing the unique items at boutique stores; you could find the ideal holiday present or a nice treat for yourself. Take a break for a warm beverage at one of the charming cafés and enjoy the festive atmosphere.

Santa at The Market at Green

The Market at Grelen

Step into a world where the holiday spirit blends with the rustic charm of the countryside at The Market at Grelen this coming November 29. This charming destination provides an escape from the hustle and bustle of the season, allowing you to explore a carefully chosen variety of seasonal delicacies and locally produced items.

As you escape to The Market at Grelen, the surrounding area’s natural beauty blends with the holiday atmosphere. Picture-perfect scenery provides a beautiful backdrop as you stroll through a haven of holiday delights. From seasonal decorations that capture the spirit of winter to one-of-a-kind, locally crafted presents, each item shows the care and craftsmanship that differentiate this countryside haven.

The Market at Grelen welcomes you to experience the enchantment of the holidays in a setting that embraces the region’s beauty and the season’s spirit.

Stay tuned for more details.

Merry Christmas lights

Orange County Tacky Lights Tour

Orange County Tacky Lights Tour is back again this year and will begin on December 1st! A FREE, self-guided tour that takes you around the County to the household’s tacky lights displays! 

Embark on a festive journey with the Orange County Tacky Lights Tour, a delightful journey around the area’s brightest-lit homes. This one-of-a-kind tour encourages you to marvel at the stunning lights that light up the night, adding a bit of quirkiness to the holiday celebrations. Print the map and discover it on your own in your car.

The Tacky Lights Tour invites those who love decorating their houses with tacky or classy lights to participate in a community-wide celebration. The route spreads joy and friendship across the community and beyond, acting as a ray of sunshine in an otherwise challenging time.

Let the Tacky Lights Tour brighten the night and bring a collective smile to the community in a celebration that goes beyond the ordinary.

Palladio Restaurant entrance

Christmas Lunch Celebration or New Year’s Eve Dinner at Palladio

Immerse yourself in the festive spirit with the Christmas Lunch Celebration, a culinary experience that captures the season’s essence. This culinary treat encourages you to sample wonderful dishes and festive flavors at local restaurants, where holiday menus and warm hospitality combine to create an unforgettable dining experience.

For an outstanding celebration, join Chef Michael Clough for a four-course meal paired with Barboursville wines. Indulge in a symphony of flavors expertly selected to highlight the finest of the season. This culinary journey, priced at $95 per person (excluding wine, tax, and service), promises a fantastic dining experience.

Reservations are required to secure your seat at this holiday table, ensuring you don’t miss out on the delectable offerings prepared with care and precision.

Wine and charcuterie board at 1804 Inn and Cottages
Guests are greeted with wine and charcuterie!

Spend the Night (or Weekend!) at the 1804 Inn and Cottages

Book a night at the 1804 Inn and Cottages if you’re looking for unique accommodations. Guest facilities can be found in four different buildings or facilities, including a stay in the historic Georgian villa on the grounds of Barboursville Vineyards. They’re all beautifully decorated for the holidays.

Guests in all rooms are greeted with a bottle of delicious Barboursville Vineyards wine from a pre-selected list. A beautiful charcuterie board enhances the wine’s taste. All guests also receive breakfast. Guests at the Inn can enjoy a hot breakfast in the dining room or their suite, while guests in the cottages need to reheat their prepared breakfast.

The 1804 Inn offers three suites that exude historic elegance. It is steps away from the Barboursville Ruins. The nearby Vineyard Cottage features two suites in a charming setting. If you want to stay in the vineyards, opt for the Blue Run Cottage with its three suites. For guests looking for privacy, the Sangiovese Cottage is perfect, as it only has one suite.

Stay in one of the beautifully Christmas-decorated suites. Make it a perfect getaway by enjoying Barboursville Vineyards and making a dinner reservation at Palladio.

Mr. and Mrs. Claus in front of White Town Hall in Orange County, VA
Visit with Mr. and Mrs. Claus

Watch the Christmas Parade in Orange

What is a holiday weekend without a traditional Christmas parade? And the Orange Virginia Christmas Parade is no exception. Parade sponsors choose a topic every year, encouraging participants to highlight a special aspect of Christmas. The parade traditionally takes place on the first Saturday in December.

One of the unique aspects of this parade is the nod to the local equestrian life. In addition to the first responders and historic vehicles, expect to see riders proudly displaying their mounts. One of the prize categories is for mounted and walking groups, so you know that they work on providing a beautiful display.

Bring your lawn chair and claim your spot along the route to view local talents. Expect to see participation from school and community groups. I enjoy watching the marching bands and seeing how local clubs interpret the theme. 

Following the parade, join everyone for the Christmas Tree Rededication around 6 pm in Taylor Park.

Christmas Open House at the Exchange Hotel and Civil War Museum

Christmas Open House at the Exchange Hotel and Civil War Museum

History lovers will want to take advantage of the Christmas Open House at the Exchange Hotel and Civil War Museum this coming December 16th from 11 am-3 pm. The building is decorated with Victorian-era Christmas decorations and offers candlelight tours. Curators dress in period costumes to transport visitors to another era. 

Visitors are warmly welcomed to experience the Exchange Hotel adorned in stunning holiday decorations, with volunteers dressed in charming period attire. The day will feature captivating historical reenactments by the 19th Virginia Infantry and a special visit from Santa Claus himself! Light refreshments will be available for guests to enjoy throughout the event. Entry is donation-based, with all proceeds supporting the preservation of the museum, kitchen house, and historic freight depot.

After greeting Santa, cap off the visit with hot chocolate and traditional Christmas sweets. 

Four County Players sign for Christmas Play
Photo courtesy of Facebook Four County Players’ Page.

Four County Players Present “Coney Island Christmas & Four County Players Fourth Annual Holiday Bazaar!”

Four County Players is bringing the holiday season to life with two exciting events you won’t want to miss! From November 22nd to December 15th, enjoy the heartwarming production of Coney Island Christmas by Pulitzer Prize-winning playwright Donald Margulies, directed by Boomie Pedersen, and based on Grace Paley’s story “The Loudest Voice.” This Mainstage show promises festive cheer and unforgettable moments—tickets are on sale now!

Adding to the holiday fun is the Fourth Annual Holiday Bazaar on Saturday, December 7th, from 10:00 AM to 2:00 PM at the Barboursville Community Center. The event will feature local vendors and artisans offering unique gifts, delicious food trucks, live performances, and a raffle with fantastic prizes.

Don’t miss this opportunity to enjoy theater, shop for special holiday treasures, and embrace the festive atmosphere with Four County Players!

We the People Love Sign at Montpelier, VA

Final Thoughts on What to Do During the Holidays in Orange County, VA

If you’re looking for a charming, small town to experience the magic of the holidays, add Orange County, Virginia, to your list!

Orange County oozes southern hospitality and charm. And that charm increases in volume during the holidays. Do yourself a favor and plan on spending a weekend or two enjoying the best the holidays can offer in Orange County, Virginia.

Have I missed any events? Please share with us in the comments!

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Happy travels,
Annick, The Common Traveler

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Holidays in Orange County, VA | The Common Traveler shares fun things to do in Orange County to celebrate the holidays in style! Enjoy small town charm in a historic setting.

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