Nestled in the heart of Virginia’s horse country, Middleburg offers a delightful mix of history, natural beauty, and small-town charm. Whether you’re planning a day trip or a weekend getaway, Middleburg has something for everyone. From scenic vineyards to quaint shops and delectable dining, here’s your guide to making the most of your visit.
Start Your Day with a Cozy Breakfast
Begin your day in Middleburg with a delightful breakfast at The Upper Crust, a cherished local bakery known for its fresh pastries and cozy atmosphere. Located at 2 North Pendleton Street, this historic house offers a variety of breakfast options that cater to diverse tastes.
Wander Main Street’s Boutiques
Stroll along Middleburg’s picturesque Main Street and discover its eclectic mix of shops. A must-visit is Every Little Something. Located at 109 W. Washington Street where you’ll find beautifully curated stationery, fine gifts and kids’ writing supplies. Whether you’re looking for a thoughtful gift, a unique journal, or a special keepsake, this shop offers treasures you won’t find anywhere else.
Savor Lunch with a View
For lunch, head to Red Fox Inn & Tavern, one of America’s oldest inns. This historic gem serves classic Virginia fare with a contemporary twist. Enjoy their famous crab cakes or a comforting bowl of soup in a cozy, historic setting.
Sip and Relax at Local Wineries
No trip to Middleburg is complete without visiting one of its world-class wineries. Some local favorites include:
- Greenhill Winery & Vineyards: A boutique winery offering exquisite tastings of Chardonnay, Cabernet Franc, and their signature sparkling wine.
- Boxwood Estate Winery: This family-owned vineyard specializes in Bordeaux-style wines, perfect for a sophisticated palate.
- Lost Barrel Brewery: just minutes from downtown Middleburg. This picturesque brewery offers a welcoming atmosphere with stunning countryside views, making it the perfect spot to unwind with friends or family.
Embrace the Equestrian Spirit
Middleburg is known as the "Nation’s Horse and Hunt Capital." Check out the National Sporting Library & Museum to learn about the town's equestrian heritage, or plan your visit around one of the seasonal horse shows or hunts.
Indulge in a Sweet Treat
Take a break and grab a treat from Scruffy’s Ice Cream Parlor or a warm drink from Cuppa Giddy Up, a local coffee shop loved by residents and visitors alike.
Dine Under the Stars
End your day with an elegant dinner at The Goodstone Inn & Restaurant, offering fine French-inspired cuisine in a romantic countryside setting. For a more casual option, try King Street Oyster Bar, where you can enjoy fresh seafood and craft cocktails.
Whether you’re a wine lover, a history enthusiast, or enjoy shopping for others, Middleburg has something to offer. Plan your trip today and discover why this little town leaves such a big impression!
