Storybook Wine Country Escape.
Scenic Roads, Gourmet Pairings & Boutique Wineries.
Leave the busy streets behind and follow one of Loudoun County's most picturesque routes through the historic villages of Leesburg and Waterford. Rolling vineyards, winding country roads, centuries-old stone homes and handcrafted wines come together in an afternoon designed to be savored rather than rushed.
An afternoon designed to be savored.
A scenic countryside drive between two boutique wineries — one pairing wine with gourmet bites, the other with artisan chocolate.
The route, and two tastings.
- The Route
Scenic Drive through Virginia Wine Country
Begin your journey in historic Leesburg before meandering along the quiet backroads toward Waterford — one of Virginia's best-preserved National Historic Landmark villages. The route itself is part of the experience, offering sweeping countryside views, historic farms, vineyards and charming rural scenery around every bend.
- Stop One
Farm-to-Table Wine Pairing Experience
Enjoy one of Loudoun County's most distinctive tasting experiences with a seated tasting of six award-winning wines, each thoughtfully paired with gourmet seasonal bites. Guided by a dedicated wine educator, you'll discover how food transforms the character of each wine while learning about the region's vineyards and winemaking traditions. This family-owned winery is the realization of a dream more than three decades in the making. After years learning the craft in California, the owners returned east in search of the perfect place to plant roots. They found it just outside Leesburg, where they transformed a 25-acre property into one of Virginia's most respected boutique wineries, blending old-world family traditions with modern winemaking techniques.
Experience includes- Guided tasting of six premium wines
- Gourmet food pairings
- Reserved seated tasting
- Educational presentation by a dedicated wine educator
- Stop Two
Guided Wine & Chocolate Pairing
Finish your afternoon with a guided tasting that perfectly showcases one of life's classic pairings. Sample six handcrafted wines alongside artisan chocolates, discovering how sweetness, texture and flavor interact to create an entirely new tasting experience. The winery entered a new chapter in 2021 when its current owners traded retirement for vineyard life after falling in love with the property. They partnered with the original founder and award-winning winegrower — who remained to oversee the vineyards — bringing together fresh energy and more than 25 years of Virginia winemaking expertise to continue producing exceptional wines.
Experience includes- Guided tasting of six wines
- Artisan chocolate pairings
- Educational pairing experience
- Reserved seating
Everything taken care of.
- Scenic self-drive route through Leesburg and historic Waterford
- Seated tasting of six award-winning wines with gourmet seasonal food pairings
- Guided tasting of six handcrafted wines paired with artisan chocolates
- Reserved seating at both wineries
- All reservations arranged
- Taxes included
- Gratuity included
A few things to note.
- Transportation (self-drive experience)
- Bottle and chocolate purchases
- Additional food or drinks beyond the curated tastings
Scenic roads and handcrafted wines.
- Scenic drive through Leesburg and historic Waterford
- Two distinctly different boutique wineries
- Two premium guided tasting experiences
- Gourmet food and artisan chocolate pairings
- Perfect for couples, celebrations and visitors looking for a relaxed afternoon
A glimpse of the afternoon.
From recent afternoons.
"The drive to Waterford was almost as good as the wine. Two very different wineries, both beautiful."
"The food pairings completely changed how each wine tasted. Our educator was fantastic."
"Everything was already reserved — we just followed the route and enjoyed a slow, gorgeous afternoon."
We don’t just tell you where to go. We know where we’re sending you.
Every place we recommend has been personally vetted, every experience is developed with our local partners, and every itinerary is designed around the people actually taking the trip.
200+ data points per venue — visited, verified, never scraped.
Co-designed with our partners, with something you won't find elsewhere.
A Field Guide of local stops, makers, and stories along your route.
We coordinate with every partner so you arrive expected and welcomed.
Good to know.
Still have questions? Our concierge is happy to help personalize your day.
Contact conciergeReservations, changes, cancellations, weather, and partner changes — all in one place.
Scenic roads and handcrafted wines.
An unhurried afternoon between Leesburg and historic Waterford — planned end to end.