
Escape the hustle and bustle of the city and immerse yourself in the charm of Loudoun County, Virginia. I recently embarked on a delightful girlfriends’ getaway with History in High Heels to this hidden gem just outside Washington, D.C., and I can’t wait to share the highlights of our unforgettable adventure. From vintage shopping to tastings and picturesque landscapes, Loudoun County proved to be the perfect blend of relaxation and excitement. Join me as I take you through our itinerary, filled with experiences that showcase why Loudoun County deserves a spot on your travel bucket list.
Pre-Stay Activity: The Old Lucketts Store
Our journey kicked off with a visit to The Old Lucketts Store, a vintage hip haven located at 42350 Lucketts Rd, Leesburg. This historic general store turned treasure trove offers a unique shopping experience. From old furnishings to new accessories, the store, built in the late 1800s, is a perfect blend of the past and present. Don’t forget to snap some photos and tag @luckettstore to share your vintage finds with the world.
Checking in: Stone Manor Bed & Breakfast
Our home away from home was the luxurious Stone Manor Bed & Breakfast. Nestled at the base of the Short Hill Mountains, this B&B offers elegant suites with Jacuzzi tubs, beautiful gardens, and a six-course gourmet breakfast. The owners are incredibly sweet and the morning breakfast is absolutely divine. It’s an exquisite accommodations that await you in Loudoun County.
Dinner: Magnolias at the Mill
For a delightful dinner experience, we headed to Magnolias at the Mill. Housed in a restored 1905 grain mill, this restaurant combines cozy ambience with exquisite cuisine. The exposed beams and historic charm make it a must-visit spot and hidden culinary gem.

First Day of Exploration:
Start your day with a sumptuous breakfast at Stone Manor, setting the perfect tone for a day of exploration in Loudoun County.
Shop Around Middleburg
Explore the charming town of Middleburg, VA, known as America’s horse and hunt capital. Visit boutiques like Chloe’s of Middleburg, Crème de la Crème, Lou Lou Boutique, and The Christmas Sleigh. Capture your shopping spree and tag the stores using the provided handles.
Lunch: Bluewater Cocina
Recharge with a casual and delicious lunch at Bluewater Cocina. Enjoy fresh tacos and more in the backyard gardens of Nature Composed. Be sure to try the catch of the day tacos and the delicious chips and queso!
Afternoon Activities: Cana Vineyards and Winery, Mt. Defiance Cidery & Distillery
Indulge in a wine tasting experience at Cana Vineyards and Winery of Middleburg and explore the handcrafted ciders and spirits at Mt. Defiance Cidery & Distillery Cider Barn. As someone who doesn’t drink alcohol I was able to enjoy the scenery, snacks, and non-alcholic drinks the winery and distillery had to offer. During the holiday seasonal time I love sipping on hot chocolate and cider while taking in Virginia’s stunning wine country. The views don’t disappoint!
Dinner: West End Wine Bar & Pub
End your day with a delightful dinner at West End Wine Bar & Pub. Surrounded by the scenic beauty of Virginia wine country, this spot combines heritage with modern dining trends. I highly recommend ordering the fried calamari, Brussel sprouts, and mocktail!

Second Day of Exploration
Savor one last gourmet breakfast at Stone Manor, making the most of your final morning in Loudoun County. Check out of Stone Manor, but the adventure isn’t over yet.
Historic Downtown Leesburg
Explore the historic downtown of Leesburg, Loudoun’s county seat. Dive into the “Holiday Fine Arts & Crafts Show” and shop around downtown boutiques like Brick and Mortar Mercantile, Zest Clothing & Co, and Rouge Spa & Boutique. Wrap up your Loudoun County adventure with a wine tasting at October One Vineyard. O1V wine is 100% estate grown on a 30-acre Loudoun County vineyard. The wines are made in very limited quantities with attention to high-quality fruit, artisan practices and painstakingly careful crafting. For my non-wine drinkers like myself, they have a lovely selection of sparkling drinks and a delicious charcuterie board to enjoy!

Loudoun County, Virginia, is more than just a destination; it’s an experience waiting to be shared. Our whirlwind getaway from the hustle of D.C. proved that Loudoun County is more than just DC’s wine country; it’s a treasure trove of experiences waiting to be uncovered. Whether you’re savoring the exquisite flavors of local cuisine, exploring historic streets lined with unique finds, or immersing yourself in the breathtaking landscapes, Loudoun County is a quick escape that leaves a lasting impression. Even if you’re not a wine enthusiast, the sheer diversity of activities, from shopping sprees to scenic strolls, ensures there’s something for everyone. So, pack your bags, hit the road, and discover the magic of Loudoun County—an experience that goes beyond the vines, inviting you to indulge in the perfect blend of adventure, relaxation, and unparalleled charm.
Cheers to new adventures and the beauty of Loudoun County!






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