Day Trip From DC: An Afternoon in Upperville and Middleburg

I recently spent an afternoon in Upperville and Middleburg galavanting around this quaint section of Virginia horse country with two fellow DC creatives, Sarah and Chesley.

We’ve talked about doing a series where we explore small towns in the DC area and this was our inaugural trip (now if only our schedules…even during pandemic times…could just align to schedule another!). My thinking is it’s similar to my DC Day Trips that I profile but with a different angle since I’m with friends rather than my husband. Perhaps it goes without say, but there’s a bit more excitement among three creative women to discover — and photograph — cute places.

First Stop: Middleburg

So, on this particular fall afternoon, we set out for a quick day trip to Upperville and Middleburg. These two horsey towns are just an hour from DC and perfect for spending a few relaxing hours. I’ve written about Middleburg quite a few times before and my takeaway is always this: it’s a charming with history and character but don’t expect to find lots to do there. It’s a place to escape from the city, enjoy a glass of wine, and wander around for a short bit. You’re probably not going to fill a whole weekend within the town itself rather it’s best as a jumping off point to explore the rest of Loudoun County.

Strolling Around  Middleburg

The town of Middleburg is essentially one street that runs several blocks. On Washington Street, you’ll find shops ranging from antiques to thrift shops to high end clothing to, no surprise, horse accessories. We popped in a few, starting at the Middleburg Antique Emporium. You won’t find any deals here but, if you’re looking to outfit your home in stunning antiques that would be right at home in a centuries-old Virginia country home, you’ve found the right place.

We stopped in The Christmas Sleigh, a year-round Christmas shop, because why not?! I may not decorate for the holidays but I do secretly want to live in a Nordic village so this is kind of my dream. Crème de la Crème is always worth a stop for charming home goods (if that name sounds familiar, it could be because they also have locations in Richmond and Frederick).

Our last stop before heading on to Upperville was Highcliffe Clothiers, which has a British sensibility that I absolutely adore (which often comes along with a Euro-worthy price tag that I don’t).

Of course, there are lots more shops along this main drag, certainly enough to keep you busy for a few hours, popping in and out of small boutiques, grabbing a coffee along the way, stopping for a sandwich, and making an afternoon of it.

Grab a Glass at Greenhill Vineyards

We actually came back to Middleburg at the end of our afternoon to raise a glass to a day well spent. We stopped by Greenhill Vineyards, which has the most fabulous views and enjoyed a chilled white on the back porch. Greenhill is one of my favorite vineyards in Loudoun County and a must-stop when you’re in the area.

 

afternoon in middleburg - day in middleburg

afternoon in middleburg - day in middleburg - red fox inn

afternoon in middleburg - day in middleburg - red fox inn

afternoon in middleburg - day in middleburg

afternoon in middleburg - day in middleburg

afternoon in middleburg - day in middleburg

afternoon in middleburg - day in middleburg

afternoon in middleburg - day in middleburg

afternoon in middleburg - day in middleburg

 

Second Stop: Upperville

Upperville is a lovely little stop to drive through but, in full disclosure, we didn’t find there was much beyond historic homes. I could 100% be wrong — and please tell me if I am!

However, I do think it’s worth a quick drive just to see how charming it is and imagine yourself living a slightly more pastoral life. Plus, there is one stop you can make in Upperville..

Sit Down for a Warm, Comforting Meal at Hunter’s Head Tavern

Hunter’s Head Tavern is a gastropub owned by a local farm, Ayrshire Farm, and serving pub-inspired dishes. You’ll find fish and chips, Shepherd’s Pie, and chicken schnitzel alongside burgers and soups. In normal times, there’s a cozy tavern-like interior that feels like stepping back in times. In pandemic times, there’s wonderful outdoor dining space.

Final Thoughts on an Afternoon in Upperville and Middleburg

You could make an overnight trip of these two horse-country destinations by staying at the Red Fox Inn in Middleburg, however it’s perfect for a weekend afternoon when you have 4-5 hours that you’d like to spend outside of the city. You’ll have enough time to see everything you’d like to see, plus stop by a vineyard on the way home. And isn’t that all we’re looking for right now?

 

afternoon in upperville - day in upperville

afternoon in upperville - day in upperville

afternoon in upperville - day in upperville

 

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