Loudon County, VA: Leesburg

Leesburg, VA

Leesburg is a city with about 40,000 people about 35 miles northwest of Washington DC, on the edge of Virginia’s wine country. The city is not named after Robert E. Lee, as I thought, but after Thomas Lee, a political figure from the 1700s.

South King Street, Leesburg, Loudon County Virginia

South King Street, Leesburg

After reading a story in the Washington Post about how the smaller cities around DC, such as Leesburg and Frederick are in the midst of a resurgence after going through an emptying-out of their downtown cores in the late 20th century. I’ve been noticing that trend for a few years, especially in my own neighborhood in D.C, and I think it’s a good thing.

I spent all of my time in the Leesburg Historic District, a walkable downtown grid with a lot of shops, restaurants, and cafes occupying a great mix of Classical Revival, Greek Revival, Georgian, and Victorian buildings.  I started my day at the Market Station, a former mill complex converted into a collection of restaurants, cafes, and offices occupying several restored buildings. It reminded me a lot of San Francisco’s Pier 39.

Leesburg Virginia


I was starving so I used Yelp to find at Market Station a good sandwich shop called South Street Under. The reuben sandwhich I ordered was amazing. There were a bunch of tables outside the restaurant in a little courtyard within the mill complex. Right outside the mill there is this little stand called Loco Beans that sells roasted coffee beans. I  bought a pound of beans from the guy and can’t wait to try them. His little stand emits all throughout Market Station a great smelling cloud of coffee.

Leesburg Virginia

Market Station

Leesburg Virginia

19th century homes

Leesburg Virginia

Typical street scene

Leesburg Virginia

Ollie getting his tour on

 During the next hour I explored the rest of the Historic District and took pictures of the great streetscapes framed by the fall foliage of a crisp fall afternoon. King Street, or Rt. 15, is the main drag, with a couple of other streets bisecting it. I was surprised how many shops there were and how many people were out on the streets–the last time I was here, about two years ago, the city seemed pretty empty.
Leesburg Loudon County Courthouse

Loudon County Courthouse

I found a  wine shop right in the heart of the Historic District called Leesburg Vintner, which is right in the heart of the Historic District. The owners didn’t mind that I brought Ollie inside, so I bought a couple of bottles in appreciation. They gave me a good run down of the wineries in the area and gave me a winery map.

Winery: The Barns and Hamilton Station

The guy at the Leesburg wine shop told me that most wineries in Virginia are dog-friendly, so I got the idea to visit one one the way home. Trusty Yelp pointed me in the direction of The Barns, a little bit north of Leesburg. I loved everything about this place: the easy parking, a BBQ truck in the parking lot, the beautiful rural scenery and vineyards covering the landscape, the farmhouse and barn–shall I go on? There was live music inside the main wine tasting room, which was full of people enjoying the late afternoon. I brought Ollie inside and tasted a few types of wine before buying a really great tasting Cabernet Franc.

The Barns at Hamilton Station

The Barns at Hamilton Station, main floor

The Barns at Hamilton Station

Tasting area

Purcellville, VA

I spent a total of about 20 minutes in this town but thought it was pretty cool.  The old historic district, which has a bunch of good examples of Victorian-era architecture, consists basically of one main street and a couple of cross streets with a few restaurants and antique stores. I locked up Ollie in the car and briefly went into Catoctin Creek Distillery Company to get some bourbon but they didn’t sell any there. Looked like a cool place to hang out though. There were a lot of people inside this fully functioning distillery, even a bachelorette party.
Catoctin Creek Distillery (on right)

Catoctin Creek Distillery, Purcelville

I looked over at Ollie, who was clearly dead tired. He gave me those eyes and I decided that we had enough fun for the day and it was time to go home.

Recap: Loudon County offers a wide selection of things to do on a nice fall weekend:  wineries, historic towns with tons of shops and restaurants. All within an hour and fifteen minute drive from downtown DC.

South Street Under Leesburg Virginia

South Street Under (Leesburg, VA)

King Street Coffee in Leesburg Virginia

King Street Coffee (Leesburg, VA)

  • Leesburg: South Street Under, a great sandwich shop and cafe in the Market Station complex. A lot of families were there getting lunch. Friendly servers and a lot of seating outside if you are with a dog.
  • Leesburg: King Street Coffee, inviting cafe with warm decor in the first floor of an old house. I saw a few people who looked like they were spending their afternoons here. Served up a good pumpkin spice latte. There are a few rocking chairs out on the porch and another seating area in the small parking lot if you have a dog.


  • Leesburg Vintner: Wine store right in the middle of the Historic District. Has a good selection of Virginia wines as well as international ones. The two really friendly owners didn’t mind that Ollie was there with me. One spent time trying to locate the best winery for me to visit with my dog and gave me a wine map of Virginia. The prices seemed pretty fair compared to what places charge in DC.
  • Hamilton, VA: The Barns at Hamilton Station (winery): one of the best looking wineries I’ve ever seen. The rustic atmosphere of the barn and farmland makes you feel as if you were in the middle of Appalachia. Dog friendly. Dogs are allowed in the bottom floor of the barn but not on the main floor. But since there was a wedding going on in the bottom floor, one of the wine pourers said it was ok if Ollie was on the main floor with me, as long as he kinda stayed out of view.


Kevin is based in Washington, DC and writes about his travel adventures in the Mid-Atlantic region and around the world. Through entertaining writing and eye-catching photography, he aims to provide readers with useful information as they plan their next trips.

  • Joanne Craw

    Sounds like a nice side trip from DC! Next time we come down we should do one of theses instead of only the city! Blog makes it so inviting! ❌⭕️?

    Sent from my iPhone


  • Joanne Craw

    this does looks so much better on the computer than the phone. I enjoy reading about these places so much and want to take a trip down. Glad you are writing! Enjoy! Love the coffee shops and food pics! Date: Sun, 2 Nov 2014 12:12:36 +0000 To: joannecraw@hotmail.com

  • Trev Trev

    Glad there was a wedding so that Ollie received special access!

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