Modern Travel: Wining and Dining in Loudon County, Virginia

An even dozen communities pleasantly sit under the Loudon umbrella and here, we’re shining a light on wineries and dining in Middleburg and Leesburg.

It’s only a little over an hour’s drive west of Alexandria (which I invite you to read all about here) and it makes for a delightful day trip.
I went with my colleague Nancy for a day of living the Loudon life and since Virginia is famous for their wines, we did two wine tastings at two very different wineries, grabbed lunch and dinner and made sure to satisfy our sweet side with an ice cream because, well, ice cream!

Use this as your roadmap or be inspired by it as you craft your own itinerary to enjoy this special part of Northern Virginia.

Boxwood Estate Winery

Featuring one of the most unique tasting rooms I’ve experienced, Middleburg’s Boxwood’s Cave Room is an elevated experience in a lower-temperature room. Yes, they have blankets if you need to warm up a touch.
During a tasting, we experienced select wines from their collection and they included a concise guide to wine tasting because we’ve all got different experience levels.
A charcuterie board paired well and the service was quite good. 

Attached to their production facility, this cozy (despite it’s large appearance) room is lined with French oak barrels for a truly special experience.
Wines offered include Merlot, Cabernet, Cabernet Franc, Malbec and more.
There’s a patio if you prefer to enjoy natural light, or visit twice and experience both settings.

50 West Vineyards

Also in Middleburg, 50 West Vineyards, named after the neighbouring Route 50, offers serene views of the Bull Run Mountains. Their authentic Virginia wine is offered via Cabernet Franc, Vidal Blanc, Ashby Gap and others. A beautiful charcuterie board accompanied our wine tasting and the service here was outstanding and engaging.
The upper covered patio has seats aplenty and the best seat is on a sofa-style seat, overlooking the mountains. Sure, the outdoor seating on the main level is good, as are the indoor seats. However, on a breezy, warm and bright day in the shade, this is where and how to spend an afternoon.
Plus, it’s pet friendly. Reservations are suggested but not standard. 

King Street Oyster Bar

In the heart of Middleburg is King Street Oyster Bar, complete with patio seating because somehow, everything tastes better on a patio with wonderful weather.
Choose from tacos (which we had!) salads, sandwiches, a good variety of entrees through this upscale yet approachable menu. 

Shutters on King

Located in neighbouring Leesburg, only 25 minutes from Middleburg, is Shutters on King, a modern American restaurant with a rooftop bar in a beautiful three-level space.
I’m a big fan of chicken wings and the presentation here was quite special. Not quite fancy but certainly better than the usual slap-them-on-a-plate-and-serve-style. There’s also steak, seafood, salads and more on the menu.
When you go, get a booth and take a close look at the intricate detail in the seat fabric. 

Goosecup Coffee

A minute from Shutters and along the famous Leesburg Coffee Corridor, with nine coffee spots on or along King street, is Goosecup. They brew the coffee fresh, have a good selection of treats and there’s an outdoor seating area, which you should experience.
An iced coffee on a warm day go together like me and chicken wings. 

Piedmont Drip & Dip

We had ice cream in Alexandria and when when we found Piedmont, we had to keep the theme of ice cream alive on this trip. Across the street from the Oyster Bar, there’s flavours aplenty here and a cute backdrop for ice cream pictures.  Plus, sundaes and banana splits also grace the menu. And there’s also a solid selection of coffees if that’s your thing. 

If you’re going to visit Loudon, take a peek at their website to see what the other 10 communities have to offer.