A Wine Weekend in Northern Virginia

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Marissa Crawford
Curated By

Marissa Crawford

  • Virginia

  • Middleburg

  • Food & Wine

  • Weekend Getaways

  • Off-the-Beaten-Path Travel

  • Countryside

Advisor - A Wine Weekend in Northern Virginia
Curator’s statement

Northern Virginia has a rich history of wine production and lends itself easily to a quick weekend getaway. The scenic vineyards are often small, family-run, and personal. Living in Virginia, taking a day—or several—to explore the wineries is one of my favorite things to do.

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Day 1: Begin your wine weekend

Enjoying the firepits at Walsh Family Wine on a beautiful fall day

Head out for your luxurious wine weekend away!

If you’re driving out on Saturday, allow extra time to stop at the farmers’ and artisans’ market at One Loudoun in Ashburn.

For your first wine tasting, stop at Walsh Family Wine in Purcellville. The outdoor fire pits are a perfect spot to sit, sip, and enjoy the view. If you’re feeling a bit peckish, Walsh Family Wine also offers food.

Day 2: Boxwood Estate & Middleburg

Tasting wines during the premium cave experience at Boxwood Estate Winery

Start the day with the cave tasting at Boxwood Estate Winery in Middleburg, a premium experience of five estate wines paired with a deluxe cheese and charcuterie board. (If caves aren’t your thing, Boxwood offers a number of premium experiences, depending on your preferences.) If you’ve found a new favorite wine, grab a bottle and enjoy lunch at the winery.

Following your time at Boxwood, take a stroll in downtown Middleburg to check out the local shops, including boutiques, thrift stores, fine arts studios, and more.

In the afternoon, drive to Willowcraft Farm Vineyards, located on top of the Catoctin Ridge with fantastic panoramic views! You can take a tour of the vineyard or grab a glass to enjoy the scenic picnic area.

Day 3: Sandwiches & Mediterranean Cellars

Appreciating the scenic view of Virginia wine country

After checking out of your hotel, pick up sandwiches at Puccio Deli in Leesburg. This local NYC-style deli has lots of specialty sandwiches or create your own.

Then, drive to Mediterranean Cellars. This boutique winery brings a bit of Greece to Warrenton and has been family-run and operated for over 40 years. You must try the Rechina, made with pine resin—you won’t taste anything else like it in Virginia!

After enjoying your lunch on the beautiful patio, start your drive back home. If you’d like, you can make an additional stop at Molon Lave Vineyards.

Need to know

  • The number of wineries and vineyards in Virginia continues to expand as the industry matures and grows. The popularity is also increasing; having reservations is a must, especially if you want a unique experience.

  • Be safe. There are multitudes of private drivers and chauffeur services available. If you don’t want to worry, let me book you with someone who will handle all of the driving and navigating for you!

  • Finally, try something new! There are so many different types of wines available in the region that you don’t want to pigeon-hole yourself into the same thing you always drink. Who knows? You might find a new favorite!

Marissa Crawford

Travel Advisor

Marissa Crawford

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