If you’re searching for authentic, small-batch Virginia wine experiences, Loudoun County is the place to be. With more than 50 wineries sprinkled throughout the rolling hills, it can feel a little overwhelming to know where to start. That’s where Vineyard Voyages steps in: we’ve handpicked 15 of the very best boutique, family-owned spots—the true hidden gems—to showcase the authentic, vibrant side of DC’s Wine Country®. Grab a glass, hop on board, and let’s get to know the unforgettable local wineries you get to experience exclusively with us.
The Vineyard Voyages Hall of Fame: Our 15 Partner Wineries
Some wineries keep things big and bold, but Loudoun County hides its most memorable moments in the relaxed corners of boutique wineries, where real passion and a sense of place shine in every glass. Here’s who we proudly call our partners:
- 868 Estate Vineyards
- 8 Chains North Winery
- Carriage House Wineworks
- Casanel Vineyards & Winery
- Domaine Fortier Vineyards
- Fabbioli Cellars
- Firefly Cellars
- Fleetwood Farm Winery
- Good Spirit Farm Winery
- Hidden Brook Winery
- Hillsborough Winery & Brewery
- Kalero Vineyard
- Otium Cellars
- Williams Gap Winery
- October 1 Vineyards
Let’s dig deeper into the winemaking magic that makes three of these stand out, and then explore the rest of the must-visit destinations along our curated routes.
The Standouts: Where Passion Meets Place
Good Spirit Farm Winery: Loudoun’s New Pioneer
One of Loudoun County’s top buzz-worthy newcomers, Good Spirit Farm is where innovation and rustic charm collide. This isn’t your typical winery. Picture a beautifully transformed barn surrounded by wildflowers and vineyard rows—with a big-hearted, community-minded team who value sustainability, authenticity, and putting a little fun into every pour. The tasting room is a masterclass in laid-back comfort, offering stunning farm views and a warm welcome; don’t be surprised if winemaker Jeff himself or another member of the family stops by your table to chat about the wines or the unique organic methods they use.
The wine lineup is beautifully expressive of the Virginia landscape. Look out for their signature white blends and fresh, floral rosés, but don’t miss their small-batch reds—bold yet balanced. Good Spirit Farm is also all about events: think food truck gatherings, art markets, and live acoustic sessions that make every visit something new.
Casanel Vineyards & Winery: Family Traditions, Uncommon Grapes
Casanel is the sort of place you dream about when you imagine a classic, family-run winery. Nestled in the heart of Leesburg, this estate is owned and operated by the DeSouza family, who pour their heritage and hearts into every barrel. What sets Casanel apart? Their fearless focus on unique grape varietals—especially Carménère and Norton, two gems you won’t find many other places in Virginia.
Walking into Casanel, you’re greeted like old friends. The tasting room has that rare, cozy atmosphere, all accented by the stories from the family, who love sharing their journey from humble beginnings to pioneering Loudoun’s boutique wine scene. Their Carménère—a smoky, spicy red with deep berry notes—is a local legend. The Norton, native to Virginia, is luscious, juicy, and a real adventure for anyone who wants to taste something a little different. And their Viognier and Chardonnay are stunning for fans of white wines.
If you’re looking for an intimate day of sipping, snacking on local cheese boards, and chatting with true wine artisans, Casanel should be at the top of your itinerary.
Fleetwood Farm Winery: Sophistication Meets Garden Chic
When you imagine the perfect Instagram-ready wine escape, Fleetwood Farm Winery brings it to life. This luxurious destination features meticulously tended gardens, stunning event spaces, and a light-filled, modern tasting room with panoramic vineyard views. It’s a place where every detail—from the curated wine flights to the French bistro-inspired small plates—feels intentional and inviting.
Fleetwood leans into elegant European-style winemaking, offering crisp whites, refined rosés, and robust reds, all grown on their estate or sourced from select Virginia vineyards. The grounds are as gorgeous as any botanical garden, making Fleetwood one of Loudoun’s most talked-about wedding and special event venues. But even on a casual afternoon, you’re treated to a taste of the good life, complete with friendly staff, sweeping countryside views, and plenty of spaces inside and out for a lingering, laughter-filled afternoon.
More Boutique Gems on the Route
Every stop on the Vineyard Voyages tour has a story and a signature style. Here’s a taste of what our other handpicked partners bring to the table:
868 Estate Vineyards
Sprawling across 120 picturesque acres, 868 Estate Vineyards is a destination in itself. Known for estate-grown wines and farm-to-table fare (don’t skip the artisanal cheese pairings), 868 also hosts fun events like sculpture walks and summer music festivals. The selection ranges from light, snappy whites to bold, velvety reds.
8 Chains North Winery
This family-owned spot is dedicated to handcrafted, small-batch wines. Their rustic barn tasting room is both dog-friendly and full of friendly faces. Guests love the Cabernet Franc and the Albariño, plus there’s often live music and rotating food trucks.
Carriage House Wineworks
Carriage House leans into hospitality, offering a warm, welcoming vibe and a focus on food-friendly wines. Their outdoor spaces are ideal for leisurely picnics, and every staff member is eager to recommend a perfect pairing.
Domaine Fortier Vineyards
Old-World sensibility and New-World terroir blend beautifully at Domaine Fortier. Savor their refined Chardonnay or the house Cabernet Sauvignon while taking in panoramic views. The estate frequently features art installations and farm-to-glass events.
Fabbioli Cellars
Fabbioli brings more than three decades of winemaking expertise, and you can taste it in their consistent, food-inspired wine flights. Try the raspberry merlot or their acclaimed pear wine for something outside the box.
Firefly Cellars
Quirky, colorful, and oh-so-friendly, Firefly Cellars is all about having fun with wine. Expect playful flights, a lively outdoor patio, and occasional themed nights with music and games.
Hidden Brook Winery
This is the forest hideaway you never realized you needed. Tucked away in a handcrafted log cabin, family-run Hidden Brook offers an ultra-cozy escape. Their easy-drinking, approachable wines are perfect paired with a relaxing afternoon.
Hillsborough Winery & Brewery
Wine lovers and craft beer enthusiasts, rejoice: Hillsborough has something for everyone. The multi-level patio overlooks lush valleys, and the tasting menu hits everything from fruit-forward rosés to complex, oak-aged reds.
Kalero Vineyard
A beautiful old barn anchors this venue, with rustic charm in abundance. Kalero specializes in limited-production estate wines, and their garden setting is a stunner for spring and fall afternoons.
Otium Cellars
German winemaking roots shine at Otium, with standout varietals like Blaufränkisch and Dornfelder. The vineyard is a favorite of locals for its laid-back vibe and unique pours.
Williams Gap Winery
With sun-drenched spaces, modern architecture, and sweeping vineyard views, Williams Gap is as beautiful as its wines are delicious. Spend an afternoon tasting signature blends and soaking up the ambiance.
October 1 Vineyards
October 1 is all about the details, from their vineyard management practices to their carefully crafted releases. Reds take center stage—be sure to try their Old Vine blends.
Why We Love Loudoun: More Than Just a Beautiful Setting
The real magic of Loudoun County boutique wineries isn’t just the killer views or world-class flavors—it’s the people. When you travel with Vineyard Voyages, you step behind the scenes and into the lives of passionate winemakers, farmers, and families who shaped the land and built the culture.
Our tours are a deep dive into the art, science, and sheer fun of Virginia wine. Whether you’re a collector, a first-timer, or just out to enjoy an incredible day in the countryside, you’ll find every glass poured with purpose and every conversation filled with heart.
Ready to discover your new favorite winery? Check out our Loudoun Wine Country tours or view upcoming Leesburg VA wine tours, and secure your spot for the adventure.
Cheers—see you among the vines!
