December in Middleburg feels like stepping into a holiday postcard. The glow of shop windows, the bustle of festive celebrations, the familiar sound of carolers, and the sight of horses clip-clopping down the street all signal that the season has truly arrived. From long-loved traditions to new ways to celebrate, the month is filled with moments that bring our community together and showcase the spirit and character that make Middleburg shine. Read below to find highlights of the events, gatherings, and small-town magic that make December one of the most memorable times of the year.
Check out just a small sampling of what we have in store this November! Be sure to visit our full Events Calendar for the latest updates.
Christmas in Middleburg Week December 1-7
The first week of December kicks off the holiday season with merry events for all ages!
Salamander Resort’s Tree Lighting on December 3 and the Town Tree Lighting on December 5 set the season aglow, while the Emmanuel Christmas Shop runs December 5–7.
December 6 brings Breakfast and Bake Sale at Middleburg UMC, Christmas in Middleburg Parade Day, parade experiences at the Middleburg Community Center and Red Fox Inn & Tavern, and a Wine Dinner at Boxwood Winery. Greenhill Winery’s Christkindlemarkt runs December 6-7. The week concludes on December 7 with Cana Vineyards’ Crafts & Cheer Holiday Market and the Foxcroft Pageant, celebrating community and holiday cheer.
Stuff the Cruiser for Seven Loaves Services
On Friday, December 12 from 2-6 pm at Middleburg Safeway, join the Middleburg Police Department and the Middleburg Business & Professional Association and Stuff the Cruiser for Seven Loaves!
This drive is essential to ensuring that families have access to healthy meals; rising costs and increased demand have made that support even more critical. Each donation helps keep shelves stocked and provides vital assistance to neighbors facing tough times. Even a small contribution can make a meaningful difference during the holiday season.
During the 2024 Holiday Stuff the Cruiser event, the community contributed nearly 1,300 pounds of food for our neighbors in need. Let’s collect even more this year!
Jingle in the Burg, Jingle Jam, and Jingle Paws Parade
Middleburg welcomes the jolly season with Jingle Jam Open Late Shopping on December 4 and December 11, giving everyone the chance to browse local shops with extended hours, enjoy seasonal treats, and pick up unique gifts while supporting small businesses.
Jingle in the Burg, on December 13, is a lively community celebration featuring carolers, street performers, holiday music, vendors and fun for all! From shopping to strolling, these events bring the joy of the season to every corner of town!
On December 20, all naughty and nice canines and humans are invited to strut their holiday spirit in the annual Jingle Paws Parade from NSLM. Come in costume and compete for prizes!
Town Menorah Lighting December 14-22
The Town of Middleburg and the Middleburg Museum warmly invite the community to join in the Menorah Lighting each evening at 5:15 pm, December 14–22, 2025, at The Pink Box Garden.
Each night, a new candle is lit to celebrate the Festival of Lights, a beautiful and meaningful tradition that brings together friends, families, and neighbors. Enjoy the atmosphere, connect with friends and neighbors, enjoy special treats, and reflect on the values of hope, generosity, and togetherness that Hanukkah represents. This special event is open to all, offering a chance to share in the joy of the season, experience the spirit of the holidays, and make lasting memories in the heart of Middleburg.
Community Holiday Events For All
Middleburg is full of holiday spirit this season for the whole community to enjoy. On December 10, the Middleburg Library hosts a free screening of The Grinch, perfect for families and friends. The following day, December 11, join neighbors for the free Viva Community Dinner at Emmanuel Parish House, a warm and welcoming way to celebrate together.
On December 13, the Middleburg Humane Foundation and Tri County Feeds invite animal lovers to their Holiday Adoption Events, helping pets find their forever homes just in time for the season.
MBPA’s annual Community Christmas Brunch on December 25 at Emmanuel Parish House, a free gathering to share food, cheer, and community spirit with friends and neighbors.
Count Down to a Bright New Year with Us
Our teeny, tiny town is brimming with ways to ring in the New Year, from lively music and standout dining to memorable moments around every corner. The Stay & Dine Experience at the Red Fox Inn & Tavern, available through January 3, offers an evening of thoughtful dishes, well-crafted drinks, and live music, while Hunter’s Head Tavern brings its own magical holiday energy with great food.
At Salamander Middleburg, guests can enjoy an elegant dinner at Harrimans or join the family-friendly Pajama Jam Dance Party as midnight approaches. And at Goodstone Inn & Restaurant, a cozy, intimate setting pairs perfectly with a special five-course menu for a relaxed, celebratory night.