In Virginia Wine Country, few places evoke more holiday charm than the historic town of Middleburg. 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.

Red Fox Inn & Tavern
Red Fox Inn & Tavern

Where to Shop in Middleburg

Whether you come to shop for the day or come stay for weekend, the charm of Middleburg when shopping for the holidays is undeniable. 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.

Antiques! on Washington

Visit this treasure trove for spectacular English, European and American furniture in fine woods. Beyond the exceptional furnishings, this lovely shop has an extensive collection of art, décor, jewelry, fine lighting, antiquarian books, sporting antiques and silver. All has been expertly curated, ensuring that you will undoubtedly find something amazing that will look lovely in your home.

Antiques! on Washington for Holiday Weekend in Middleburg
Antiques! on Washington | R.L. Johnson
Middleburg Antique Gallery for Holiday Weekend in Middleburg
Middleburg Antique Gallery | R.L. Johnson

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.

The Christmas Sleigh

There is no better place for finding 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.

The Christmas Sleigh for Holiday Weekend in Middleburg
The Christmas Sleigh | R.L. Johnson

Marguerite Henry and Wesley Dennis | National Sporting Library & Museum

The literary partnership between illustrator Wesley Dennis and children’s author Marguerite Henry has brought joy to children for decades. The pair published 15 horse-related books together over the course of two decades. Currently, you can enjoy their partnership on display at Middleburg’s National Sporting Library & Museum, including 12 classics written by Henry paired with Dennis’ illustrations and paraphernalia from the Wesley Dennis Archive.

Mystique Jewelers

When visiting Mystique Jewelers, be sure to ask to see the Mazza collection (shown here). The passion for Liz, the owner and design force behind Mystique, is to design the most beautiful and unique jewelry for her customers. Having been in business for over 20 years, she has become known for her exceptional one-of-a-kind engagement rings and custom designs. Re-design is Mystique’s specialty! Their master goldsmith, Graduate Gemologist and jewelry designers will listen to your needs, then sketch and create your dream piece, making a sentimental and keepsake gift.

Mystique Jewelers
Mystique Jewelers


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. 

Baileywyck Antiques for Holiday Weekend in Middleburg
Baileywyck Antiques | R.L. Johnson
Elizabeth Locke Jewelry for Holiday Weekend in Middleburg
Elizabeth Locke Jewelry

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.

The Town Duck

Located in nearby historic Old Town Warrenton, The Town Duck is a a hostess’s dream shop. It is filled with everything from thoughtfully curated wines and fine foods to specialty gifts like baby toys, ladies wear, lovely toiletries, candles, gardening, tabletop and kitchen items. Additionally, they also will create custom-designed gift baskets to create an even more enchanting gift.

The Town Duck for Holiday Weekend in Middleburg
The Town Duck | R.L. Johnson

Where to Dine 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 Resort and 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. In nearby Millwood, the Locke Store & Buttery offer a combination restaurant and charming country store with ready-made sandwiches, hot dishes and picnic accoutrements for the perfect meal on the go.

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.

Middleburg Horses Parade
Middleburg Horses Parade
Middleburg Christmas Parade for Holiday Weekend in Middleburg
Middleburg Christmas Parade

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 walk 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.

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 Boxwood Estate Winery, Cana Vineyards, Chrysalis Vineyards or at the nearby RdV. A short drive away, Bluemont Vineyard is offering 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.

RdV Vineyards | R.L. Johnson Photography
RdV Vineyards, Image by © RL Johnson for Wine & Country Life

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.

For more Virginia-made gift guides, click here.  ~

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Virginia Wine & Country celebrates elevated living in Virginia Wine Country. Virginia Wine & Country Life is a semi-annual luxury print magazine with a full digital presence. The Virginia Wine & Country Gold Book is an annual guide to the top award-winning wines, wineries and experiences in Virginia Wine Country. The annual Virginia Wine & Country Wedding Planner is an art book of elegant Virginia weddings. The brand includes the Virginia Wine & Country Shop in Ivy, Va. It is a beautiful lifestyle boutique that brings the pages of the magazines to life. Virginia Wine & Country tells the stories of Virginia wineries, the farm-to-table movement, luxury travel, entertaining, art and the elegant country lifestyle. Ivy Life & Style Media also provides branding, web design and PR services for the wine industry.