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West to Virginia

Posted on June 6, 2026 by Ella

Our route took us from Bethesda, Maryland, past Dulles airport and westward for a first stop in Middleburg. As mentioned previously, Middleburg is a tiny town with a population of 700. White, wealthy strongly right leaning politically but situated within a county that is fast moving left. 

Bethesda to Afton

Our intention was to stretch our legs and stop for a coffee at Cuppa Giddy Up. Yep. Their espresso machine was down so we giddy-upped on down to Common Grounds where we all satisfied our caffeine needs.

Main Street in Middleburg

We popped into a historical inn that also served as an art gallery and restaurant. You can tell this is horse and hunt country by looking at the subject of every painting.


THE RED FOX INN, claims to be the longest, continuously operating Inn in the country. c. 1728.
Sly fox
Crazy horse
Cows not caring about horses or foxes

As you might imagine there are a few centuries of history here. 

Onward, west to Upperville where the longest running horse show in the country (173 years) was in progress. By the number of cars packing the grassy parking areas, it seemed like a few thousand people had showed up. We saw some young riders being led by blue-blazered attendants onto the show grounds.

We turned southward, meandering through Delaplane on a one lane country road. The promised rolling green hills and low stone walls were everywhere. Gorgeous country. 

A couple hours later, we rolled into Charlottesville hoping to find a late lunch. We parked in the historic downtown area but lunch options were slim. And then we found Tillamans, an Italian style bistro. I had a grilled cheese panini loaded the chili. Yummy.

We stopped at Wegman’s, one of those huge, upscale groceries. The biggest department was the wine department, Yay! I had found my Aperol in a liquor store in Middleburg (the Aperol was placed in a black, opaque plastic bag…perhaps the idea was to not let people see my purchase?). Wegman’s had a fine selection of Prosecco and with a staffer nearby who was happy to describe each one in order to find the perfect mate for my Aperol spritz to be.

Then a final westward push of about 25 minutes to our rural Rockridge Retreat Airbnb. Our home for the next 6 days.

Rural setting at our Airbnb
View from the deck

1 thought on “West to Virginia”

  1. niktis says:
    June 9, 2026 at 12:25 pm

    I love the forests and the greenery of this part of the country. So different from most of the west. Also the smells are much heavier and rich.

    Reply

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