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Exploring Middleburg, Virginia's Hidden Gems

Located in the heart of Virginia's Horse and Hunt Country, Middleburg is a charming historic town that beckons both locals and visitors with its rich history, idyllic landscapes, and vibrant shopping scene.

picture of Shaggy Ram Antique Gallery in Middleburg

photo from Red Fox Inn and Tavern

From antique treasures to fashionable boutiques and specialty stores, Middleburg's Historic District offers an array for those seeking unique shopping experiences. Below, in this shopping guide, Chloe's of Middleburg has included some of our favorite places to visit, besides ourselves of course, throughout Middleburg whether you are looking to shop, dine, or both.

night picture of The Red Fox

photo from Middleburg, VA

Middleburg, established in 1787, is known for its well-deserved reputation of remarkable antique galleries, which has a treasure trove of hidden treasures. Whether you are an avid collector or have an appreciation for the timeless beauty of antiques, Middleburg is the must-visit destination.

Thistlethwaite Americana

Popping into Thistlethwaite Americana is like stepping back in time. The antique gallery specializes in a wide range of Americana including museum-quality and highly collectible pieces with remarkable provenance.

Taylor Thistlethwaite sitting in his antique gallery holding different pieces of Antiques including a eagle flask

photo from Middleburg Life

Middleburg Antique Emporium and Antiques on Washington

For the discerning shopper with a love for hidden gems, Middleburg Antique Emporium and Antiques on Washington is a dream come true. These antique galleries house a diverse range of collectibles.

Middleburg’s Washington Street is home to so many great boutiques making the town a shopper’s paradise.

Wendy and Chloe posing outside their boutique located on Washington Street of Middleburg

photo from The Hunt Country Scout Guide

Le Boudoir

For the perfect blend of elegance and allure, Le Boudoir is your go-to boutique in Middleburg for intimate apparel. The boutique offers a carefully curated selection of lingerie, sleepwear, and loungewear that will leave one feeling confident and glamorous.

The Playroom

The Playroom is a whimsical children’s store that sparks joy in both children and adults. Here, you'll find a carefully curated selection of unique toys, games, and educational items that ignite imagination and creativity. Pop into this magical world and let your inner child roam freely.


Indulge your love for fine jewelry at Mystique. From statement necklaces to sparkling earrings, their one-of-a-kind pieces are sure to catch your eye. Treat yourself or find the perfect gift for someone special at Mystique.

picture of Mystique Jewelry

photo from Middleburg Life


Highcliffe is a go-to destination for men's fashion in Middleburg. Discover a range of sophisticated and stylish clothing that caters to the modern man. From tailored suits to casual wear, Highcliffe has everything you need to elevate a wardrobe.

Nature Composed

For a touch of natural beauty, visit Nature Composed, a charming flower shop that transports you to a world of fragrant blooms and stunning floral arrangements. Their exquisite floral creations will leave you enchanted, whether you're seeking a gift or simply want to brighten your day. Despite the fact they are not located on the main street of Middleburg, they are nevertheless still worth the visit.

flower arrangement made by Nature Composed

photo from The Hunt Country Scout Guide

While not situated on the main thoroughfare of Middleburg, Federal Street, and Madison boasts a collection of outstanding specialty shops. From The Village Blacksmith to The Tack Box, Middleburg Tax Exchange to Hastening Design, Middleburg Gourmet to Middleburg Essentials, and Posh Pixies to The Woolley Fox, Federal Street, and Madison Street have a diverse array of specialty stores that are sure to captivate and delight visitors.

aerial shot of Middleburg at Sunrise

photo from Visit Loudoun

Once you are done shopping or if you need a reprieve, Middleburg is home to several amazing eateries, including coffee shops, a traditional bakery, restaurants, and a historic inn.

Common Grounds and Cuppa-Giddy Up

Start your shopping day with a delicious assortment of sandwiches at Common Grounds or grab a cup of coffee to go from Cup a Giddy Up. Both coffee shops offer a cozy atmosphere and delightful brews that will energize you and prepare you to walk the streets of the historic town.

The Upper Crust

When you're craving something sweet, make your way to The Upper Crust, the town's beloved traditional bakery. The Upper Crust offers an assortment of delicious cookies, pastries, cakes, and other treats that will satisfy anyone’s craving.

fresh glazed donuts

photo from Visit Loudoun

King Street Oyster Bar

King Street Oyster Bar has cemented its reputation as one of the town's most popular restaurants among both locals and visitors. With its exceptional happy hour offerings, people flock to this restaurant to indulge in fresh and delectable seafood dishes while enjoying the lively and inviting atmosphere.

Red Fox Inn & Tavern

The Red Fox Inn & Tavern, one of the keystones of Middleburg since 1728, is noted to be one of the oldest inns in America. Beyond its rich heritage, this iconic establishment offers an impeccable culinary experience like no other, serving exceptional food made from fresh local ingredients.

christmas time picture of the historic red fox

photo from Southern Living

Middleburg, VA offers a shopping experience that combines history, style, and whimsy. From antique treasures and fashionable boutiques to delightful coffee shops and culinary delights, this charming town caters to all. Embark on a shopping adventure in Middleburg. Happy shopping!



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