Spend your holidays in Middleburg, Virginia! Few places evoke more festive charm than this historic town. Whether visiting for a day or a weekend, you are sure to get caught up in this quaint town steeped in history and centuries-old Virginia charm. Full of old stone buildings with red doors (like the historic Red Fox Inn & Tavern seen below, established in 1728), Middleburg is a fabulous place to do your holiday shopping. Its high-end restaurants, inns and boutiques all decked out in their holiday best make shopping a pleasure. This gem in the heart of Virginia hunt country makes the process of discovering that just-right gift for everyone on your list a joy and delight. You can also enjoy Christmas light displays, the annual parade, vineyards with cozy fireplaces and lots of small-town charm. To help you plan your visit, we’ve curated this guide to some of our favorite hot spots in Middleburg for the Holidays.
Where to Shop in Middleburg
Whether you come to shop for the day or come stay for weekend, shopping for the holidays in Middleburg has an undeniable charm. You’ll find something unique and fabulous for everyone on your list. Shops in Middleburg are filled with sophisticated collections from around the globe and offer everything from art, jewelry and apparel to home decor and more. There are a lot of fine antique shops here as well that make finding a one-of-a-kind gift a sure bet. While you’re in the area, be sure to stop by Afield Middleburg at the Loft, a brand-new location by beloved Virginia company Tri-County Feeds. Do your holiday shopping at this clothing boutique and support our beloved local stores!
Crème de la Crème
Crème de la Crème is the perfect shop in Middleburg to find expertly curated European-inspired home décor. From elegant table linens and dishware to whimsical accent statuary and carpets, the store truly represents the cream of the crop when it comes to decorating your home for the holidays. While there, fill out your Christmas gift list with some of the beautiful jewelry or candles and home fragrance they have on display, or buy a loved one one of their unique hand-crafted French porcelain Guinea Hens from Provence for a one-of-a-kind décor statement.
The Christmas Sleigh
There is no better place to find charming Christmas décor than this traditional European shop that has been named one of the best Christmas shops in the United States. It is filled with classically beautiful German and Austrian ornaments, nutcrackers, art, bells, beer steins, nativity figurines, music boxes, collectible figurines and wonderful décor. A true wonderland of Christmas goodies, The Christmas Sleigh has unique handmade gifts for everyone on your list, and a whole room is devoted to gorgeous European winter apparel as well.
Hastenings Antiques
Hastening Designs is a premier destination for lovers of fine antiques. The shop features a curated collection of 18th- and 19th-century European furniture, artwork, and decorative objects, with pieces from France, Italy, and England. Beyond offering rare and elegant antiques, owner Louis Shields provides interior design services, helping clients seamlessly integrate historical treasures into their own homes with sophistication and style.
Middleburg Antique Gallery
With 45 dealers, the Middleburg Antique Gallery is filled with dozens of fine collectibles and is located in a beautiful stone structure in the heart of Middleburg. They pride themselves in having a large Staffordshire collection of both dogs and figurines from which to choose, along with art, jewelry, lamps, chandeliers, antiquarian books, oriental rugs, fishing and sporting antiques, and American sterling, English hallmarked and coin silver.
National Sporting Library & Museum
Celebrate the season with a visit to the National Sporting Library & Museum in Middleburg, where art, history, and the spirit of the countryside come alive amid festive charm. Wander through elegantly curated galleries showcasing equestrian and field-sport heritage, explore rare volumes in the inviting library, and enjoy special holiday programs that illuminate the region’s sporting traditions.
Roger on Madison
Roger on Madison is a thoughtfully curated antiques shop reflecting the personal taste of owner Linda Mason. The store offers an eclectic mix of furniture, artwork, and decorative objects, ranging from accessible treasures to striking statement pieces. With a rotating selection inspired by seasonal themes and frequent new finds from seasoned dealers, Roger on Madison combines a welcoming, stylish atmosphere with the thrill of discovering unique, timeless antiques.
Shops Not to Miss Near Middleburg
Baileywyck Antiques
We love the wonderfully curated collection at Baileywyck Antiques. This shop, housed in a converted firehouse, is nestled in the charming village of The Plains just a few minutes from Middleburg. Inside, you will find a highly-curated selection of gorgeous period furniture and home furnishings, including lighting, rugs, textiles, artifacts, accents, architectural pieces, tabletop items, distinctive gifts and an array of equestrian-themed art. The lovely shop is also next door to a few delightful local boutique restaurants.
The Other Elizabeth
Located in nearby Boyce, The Other Elizabeth is the world headquarters of Elizabeth Locke Jewels. While her pieces are found in high end stores like Neiman Marcus and other fine shops, including her one on Madison Avenue in New York, this gorgeous boutique is housed in an historic 19th-century Virginia building which has been transformed into an Italian palazzo. The shop is the perfect place to showcase Locke’s neoclassical jewels and is truly a treat to see. Open Saturdays and Sundays noon to 5, appointments are recommended.
Where to Dine for the Holidays in Middleburg
The Tavern at The Red Fox Inn offers a very cozy ambiance reminiscent of a Charles Dickens novel that makes it an ideal location to relax and enjoy a delicious meal after a day of holiday shopping either in the casual bar and cafe or the fine dining restaurant. Both Salamander Middleburg and The Goodstone Inn also offer award-winning dining options nearby for a special holiday dinner.
In the center of town the King Street Oyster Bar is a favorite with Middleburg residents, with its dedication to offering 10+ varieties of the freshest U.S. oysters, which are served within 24 to 48 hours of being caught. They also serve the self-proclaimed best Sunday brunch in Middleburg, making them an ideal choice on your weekend trip.
For a quick pick-me-up while you’re out shopping, Middleburg has some lovely cafes. A few local favorites are Middleburg Common Grounds, Market Salamander and Cuppa Giddy Up. Serving sandwiches, as well as a wide range of coffee drinks and select beer and wine, they will help keep you fueled and ready to keep taking in all the sites.
Holiday Events in Middleburg
One of the most popular events during the holidays is the beloved Middleburg Christmas Parade. This parade features horses, hounds, ponies, llamas and more and typically attracts thousands of visitors, so be sure to plan your visit accordingly and early if you’d like to attend.
Beyond the parade, there are still plenty of festive ways to celebrate the Spirit of Christmas in Middleburg throughout the holiday season. The annual tree lighting marks the beginning of a festive season that will include horse-drawn carriage rides, Santa experiences and wine-paired meals, as well as plays, concerts, gallery exhibits and more. Visitors can also join Middleburg for the ultimate Charles Dickens Christmas Experience with special Dickens-themed events such as the Dickens of a Dog Show, the Run Like the Dickens 5k two live outdoor performances of “A Christmas Carol,” and much more.
A bit farther afield, in nearby Upperville, the historic Oak Spring Gardens are dressed up for the holidays. Oak Spring Garden Foundation is the living legacy of legendary horticulturist and philanthropist Rachel “Bunny” Lambert Mellon. The estate’s lush gardens, rare plant collections, and carefully preserved archives offer a serene retreat for lovers of beauty, art, and nature. Each holiday season, the foundation welcomes visitors to celebrate in style, with festive tours, seasonal floral displays, and charming family-friendly activities that bring the magic of the gardens to life.
Holiday Lodging in Middleburg
When planning a weekend getaway to Middleburg, the first step is to reserve your hotel room. For a true step back into old world luxury, there is no better place than the historic and festive Red Fox Inn & Tavern. Located in the heart of the village, it is an ideal home base for your trip. Check their website to discover special holiday meals, events and packages.
Just a short drive away is the world-renowned Salamander Resort and Spa led by the incomparable entrepreneur Sheila Johnson. This 340-acre equestrian resort is the only five-star luxury resort in the Washington, D.C. area. Designed to provide its guests with an unparalleled Virginia holiday experience. Seasonal events include brunch with Santa, a festive game of elf on the shelf and a four-course Christmas feast featuring traditional holiday dishes.
A little further afield, the Goodstone Inn is a romantic boutique hotel offering a variety of private cottages and luxury accommodations for when you want to experience an idyllic getaway for the holidays. The Inn sits on 265 acres of private, peaceful land tucked away in Virginia wine country. Guests have the option of staying in one of 18 guest rooms spread across six historic cottages and houses. Each room features charming European décor, luxurious linens and king-sized beds. The hotel is built on the values of sustainability and farm-to-table living, featuring an animal farm, fresh gardens and an apiary on property. The Conservatory at Goodstone Inn offers fine dining for guests and visitors alike, with a special focus on seasonal ingredients sourced on-grounds.
Nearby in Hume, Marriott Ranch is a wintertime retreat where rustic charm meets refined comfort. Guests can cozy up by the fire in the Inn at Fairfield Farm, savor a hearty country breakfast, and enjoy the serene, snow-dusted landscapes that stretch across 4,200 acres. The estate’s historic manor house and versatile event spaces make it an enchanting setting for intimate holiday gatherings, festive dinners, or family celebrations, all enhanced by attentive service and the warmth of a true Virginia country escape.
Holidays in the Vineyards
Visiting vineyards in Virginia wine country over the holiday season is its own experience. Not only can you grab a bottle of your favorite wine to gift to someone special, you can enjoy special events and tastings and enjoy cozying up with a loved one near a festively-decorated fireplace. In and near to Middleburg you can enjoy tastings at Cana Vineyards, Barrel Oak Winery or Slater Run Vineyards. A short drive away, Bluemont Vineyard offers the chance to enjoy their magical hillside of vines decorated in twinkling lights, creating an ethereal experience. They also offer a wine and chocolate pairing event in January.
No matter who you’re shopping for, we hope this guide to Middleburg for the Holidays offers inspiration to help you make the most of your visit to Northern Virginia this season.
Want to even more Middleburg inspiration? Check out our A Weekend Guide to Visiting Middleburg for a more in-depth look at where to stay, where to eat, the best vineyards to visit and more shopping advice. For more holiday outing ideas, see Holidays in Loudoun’s Wine Country, and don’t miss the list of these Loudoun Wineries to Visit or these Five Charming Places to Visit in Loudoun. ~
