One Day in Leesburg, Virginia


One Day in Leesburg Virginia (Pinterest)

When you think about the fact that we sold all our belongings and hit the road, you might think we hated our hometown.  But nothing could be further from the truth.

Leesburg, Virginia is a small town in northern Virginia about 40 miles northwest of Washington, DC. We lived there for some of our college years and even had our wedding there at the gorgeous Birkby House.

Birkby House wedding - Our Streamlined Life

We left Leesburg for a few of our early married years but moved back in 2013 — this time to a cozy apartment in the heart of old town. We absolutely loved taking full advantage of everything downtown living had to offer. So, without further ado, here are our recommendations for spending one day (or a weekend!) in Leesburg, Virginia.

Breakfast in Leesburg, Virginia

  • The Leesburg Diner is our favorite breakfast spot just a couple of blocks from our old apartment. Ryan loves their steak & eggs and my pick was the Greek omelette. This spot has a friendly and welcoming true diner atmosphere. [9 S. King St, Leesburg, VA 20175menu]
  • King Street Coffee has excellent coffee, but it’s also my pick because their gluten-free muffins are the best I’ve had.  (The chocolate-ricotta muffin is better than most regular muffins I’ve had.) They also have a lovely selection of “normal people” pastries. [110 S King St, Leesburg, VA 20175]

Lunch in Leesburg, Virginia

  • Trinity House Cafe is a new addition to the downtown scene, but their sandwiches, salads, and appetizers are hearty and delicious. The Guadalupe is technically an appetizer, but it’s big enough to make a delicious lunch. The Trinity House Salad is also awesome, and Gram’s Hot Chocolate always hits the spot.  Bonus: wine and beer are also available. [101 E Market St, Leesburg, VA 20176menu]
  • Shoes Cup & Cork is another favorite lunch spot, also serving up soup-salad-sandwich options. It’s a little trickier for me now because they don’t have a ton of gluten-free options, but the atmosphere is so great I don’t even care. I usually enjoy the Tomato Caprese Salad while Ryan vouches for most of their sandwich options! [17 N King St, Leesburg, VA 20176menu]

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Dinner in Leesburg, Virginia

  • Los Tios Grill is my favorite Mexican restaurant in the whole world. Literally. On our road trip I kept dragging Ryan to Mexican restaurants and leaving disappointed: “It was okay … but it wasn’t Los Tios.” I get the bean enchiladas, Ryan gets the seafood chimichangas, and when they ask if you want a large margarita, say yes. [201 Harrison St SE, Leesburg, VA 20175menu]
  • MELT Gourmet Cheeseburgers has won both “Best Burgers & Fries in Loudoun County” and “Best Burgers & Fries in Virginia” and both awards are fully justified. The strip mall location is unimpressive, but it is always packed because it’s just that delicious. Their veggie burger is the best I’ve ever had (bonus: gluten-free buns) and Ryan invariably chooses the Bacon-Blue Burger. [525 E Market St, Leesburg, VA 20176menu]
  • I couldn’t make a dinner list without mentioning Giovanni’s NY Pizza. It’s the only pizza in town that satisfies Ryan’s New Jersey sensibilities, and was a recurring staple in our house before I went gluten-free. (Not only is the pizza awesome but the guys who run it are hilarious, too.) Don’t skip the garlic knots! [520 E Market St, Leesburg, VA 20176menu]
  • For an upscale dining experience, our Leesburg favorite is Tuscarora Mill (known locally as “Tuskies”). This was a special occasion, birthday-and-anniversary favorite for us. Their menu changes seasonally and we always leave raving about the food! [203 Harrison St SE, Leesburg, VA 20175menu]

Outdoor Fun in Leesburg, Virginia

W&OD trail - Our Streamlined Life

  • My favorite way to spend a beautiful day in Leesburg is walking (or running) the Washington & Old Dominion Railroad trail. This 45-mile trail begins outside Washington, DC and runs through Leesburg from ~miles 31-36. There’s a nice spot to get on the trail on S. King Street (although street parking can be difficult to find). [map]
  • Ida Lee Park is the “crown jewel” of the Town of Leesburg’s Parks & Rec Department, and it’s the perfect place to take a picnic lunch. If you park at the library you’ll have easy access to the walking trail, a playground, and some gorgeous wide open spaces. [60 Ida Lee Drive NW, Leesburg, VA 20176]

Indoor Fun in Leesburg, Virginia

  • Cobb Theatre is located outside the downtown area, but it’s our go-to spot for fun on a rainy day. This movie theater is relatively new, is clean and spacious, always has the best movies, and offers a full bar and an excellent menu. [1600 Village Market Blvd, Leesburg, VA 20175]
  • The Tally Ho Theatre used to be an inexpensive downtown movie theater but has since been converted into a live music venue. It has a fun, intimate vibe and hosts great local bands. (Occasionally they get some better-known artists like Vertical Horizons and the Gin Blossoms.) [19 W. Market Street, Leesburg, VA 20176]

And there you have it, folks! If you ever have the opportunity to visit Leesburg, I hope these recommendations will come in handy.


I’m the oldest of 12 crazy kids and two pretty awesome parents. My love of travel developed during my early years traveling the globe as an Air Force brat. I’m a runner, a writer, and a reader, and I love cooking up good food and cozying up our camper.

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