Travel Guide: A Weekend in Middleburg

A few weeks ago, I headed out to Middleburg, Virginia, an equestrian town just an hour from DC, and I wondered how on earth I had never made the trip out there before. I’ve been on plenty of vineyard tours that go out into Loudoun County, where Middleburg resides, but had never gotten in the car to spend a day in this small town. So, let me start this post by saying, if you haven’t been out there, block out a Saturday or Sunday this summer to spend a weekend in Middleburg.


Spending a day in Middleburg is an exercise in slowing down and savoring the day. It’s a charming small town with excellent wine and food, and that’s you go there for. To drink, to eat, and to stroll the streets. While I often like to pack my weekends away with activities and things to do, I had to learn a lesson in enjoying these moments of downtime. Sometime mid-afternoon, I found myself asking if there was anything else left to explore, and the answer was, no, just go to the cidery, sit outside, enjoy this perfect 80 degree summer day, and relax. So, that’s what I did, and I don’t regret it one bit.

Also, it’s worth noting before I dive into my recommendations that everything is within a 5 minute drive, with most of it being walkable in downtown.



I’ve been to a lot of the vineyards around the Washington, DC area and Greenhill Winery and Vineyards is definitely up there at the top. Often with tastings, you feel a bit like you’re being shuttled in and out as quickly as possible to get the next group in. Not at Greenhill. You take a seat on the back porch, gaze out over the rolling hills, and your tastings come out at a leisurely pace, one at a time. And the wine is excellent – so good, in fact, that it made an appearance in the goodie bags given to guests at the Oscars. You could spend a few hours doing a tasting, then indulging in a bottle of your favorite of the wines, and, of course, having a few snacks to soak it up.

It took a lot of convincing to tell Adam that, no, we do not need to join a wine club given how much alcohol is currently at our apartment…but I have a feeling we’ll be joining as soon as he cancels our current wine club membership.



Once you’re feeling warm and fuzzy from the wine, it’s obviously time for some art. As someone who majored in Art History and actually did one of my two seminars on 19th century British art and grew up with hunting dogs, sporting art is near and dear to my heart – I even have several sporting prints in our living room gallery wall – so I was delighted to visit the National Sporting Library & Museum. It’s not a huge museum, which is perfect for working into your weekend itinerary, and it’s filled with paintings of horses, dogs, and everything that comes to mind when you think of Middleburg. We spent about an hour there and it was a wonderful afternoon respite in between all of the eating and drinking.



You’ll want to stop for lunch at some point in downtown Middleburg and I would recommend King Street Oyster Bar. We sat outside, enjoyed some oysters, naturally, as well as the oyster po’ boy and the crabcake benedict. All were delicious and you just can’t beat a gorgeous afternoon eating al fresco.

Once you’re full from lunch, it’s time to get walking. Stroll the streets of downtown Middleburg, pop in the chic clothing stores, the collected secondhand stores, and marvel at the offerings at the Middleburg Antique Emporium – not only do they have gorgeous antiques, but also an impressive selection of costume jewelry.

If you work u an appetite again from all of those steps, stop in Popcorn Monkey for a quick snack to bring along with you. We ended up with a sweet and savory mix that accompanied us on the next activity of the afternoon – a distillery and cidery.



Our afternoon in Middleburg took us to both of Mt. Defiance‘s locations. First, we stopped by their downtown tasting room, where I did a chocolate and liquor pairing, and Adam had an absinthe cocktail. Then, we went up the road about 3 minutes to their new cidery barn, where we each got a glass of their crisp, refreshing cider and just sat on the front porch for a couple hours relaxing and taking in the gorgeous late spring day.

We asked the bartender for her recommendations on what else to do in town, and she said “we eat and drink here, and that’s about it.” And that is when I realized that a trip to Middleburg is all about slowing down and enjoying the moment. There wasn’t any “Is there something we need to do that we’re missing?” FOMO, instead I focused on just taking in the scenery, sipping on a beverage, and enjoying the company.



I wasn’t quite sure where to include Common Grounds, because we actually ended up having two meals here over the span of a day. I had a coffee meeting early in the morning at Common Grounds on Monday, with the intention we’d drive right back to DC from there. Instead, we decided to hang out and work from Middleburg all day long. It was so lovely out, that we took advantage of the wifi, sat outside, and lived that remote work life. The coffee was great, the sandwiches were amazing, and I loved watching small town Middleburg unfold in front of me – seriously, I eavesdropped on so many gossipy conversations and saw so many people run into their neighbors. I loved it.




Middleburg is just an hour west from DC on I-66 and I-50. It’s a quick drive and, like I said earlier, I can’t believe this was the first time I’d made the trip! It’s so close, yet a world away. I would recommend going in spring, summer, or fall – it’s an easy trip to work in if you happen to wake up one summer day, find that it’s beautiful out, and decide to get in the car and go.


There will be an entire post on my stay next week, but I can’t recommend The Red Fox Inn and Tavern enough. It’s one of those places that is historic, yet doesn’t feel stuffy. I’ll share so much more in my post, but it’s charming, it’s comfortable, and I cant wait to go back – both to the Inn and to Middleburg.





  1. Laura Leigh Elliott
    June 11, 2018 / 4:40 pm

    100% want to go here now! I love how you said "Spending a day in Middleburg is an exercise in slowing down and savoring the day" I want to slow down and savor the day – that is right up my alley and what is needed in the summertime. Thanks for sharing lady!xo Laura Leigh

  2. Kiersten
    June 14, 2018 / 7:08 am

    I love Middleburg. My dad is from that area of Virginia so we’ll take weekend trips up there. Winery hopping in NoVA is a lot of fun too.

Leave a Reply