Itinerary: Charming Leesburg, VA
A “mini-tinerary” that explores a small, sparkling town with a healthy helping of history.
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Leesburg, VA was an unexpected surprise, truly. My husband and I didn’t even realize we were staying in Leesburg when we first arrived (complete oversight that’s not typical for a Type A planner!).
We were there for an event in nearby Bluemont and as we were only there for one full day, we didn’t make any plans for our downtime.
But when we popped in for dinner before checking into our hotel on Friday night, we discovered a lively and beautiful town waiting to be explored! Naturally, we spent our Saturday morning hitting the highlights before attending our event in the evening.
This mini itinerary (or mini-tinerary as I’m choosing to call my weekend guides) was designed based on our weekend exploring Leesburg but built in a way that makes up for the time that we spent at our event since that wouldn’t be applicable to most people coming to this quaint town for vacation.
Day 1:
If you’re flying in for the trip, you’ll want to select Dulles (IAD) as your destination airport. It’s a quick 30-minute drive from the airport to the heart of Leesburg.
We stayed at the Best Western only 5 minutes from historic downtown Leesburg, and there are a lot of other typical hotel brands in the area. If you’re looking for something a bit more upscale for your stay, Hotel Burg is a 4.5🌟 luxury boutique hotel that looks like a great choice.
With logistics out of the way, you can dive right into an evening out on Leesburg’s “Restaurant Row”. With pleasant weather comes the light hustle and bustle of fellow patrons dining outside.
Pro tip: Town Hall parking garage is free from 5:30PM on Friday until 7:00AM on Monday. Save a few bucks on parking all weekend long!
Start at Lightfoot for your main meal (my recommended appetizer is the Seared Sea Scallops which are set on sweet potato pancakes — delish!). Indulge in a glass of wine, a Lightfoot draft beer (my husband was a big fan of this one), and a hearty dinner. Finish off the night at Rebellion next door for bourbon or a craft cocktail before calling it a night.
Day 2:
Start your morning at Second Nature Coffee, a popular and charming coffee shop on King Street. I wasn’t in the mood for coffee so I opted for an unsweetened strawberry oolong iced tea. The honey cinnamon cappuccino stuck out to me however, and I would’ve like to try that in addition to one of their tasty looking pastries!
Next up, I hope you brought your walking shoes because there’s a lovely park and trail system at Ball’s Bluff Battlefield Regional Park. Learn all about the Civil War battle that occurred here while wandering through nature, all for no cost of admission. Spend 30 minutes to an hour here before moving on to your next stop.
Before you pop into a restaurant for lunch, make a stop at Loudoun Museum a block away from King Street. This free admission museum is situated in an old house and shares lots of interesting history about the area. I particularly enjoyed their keen focus on African American history and Women’s history in Loudoun (the county Leesburg sits in).
For lunch, head over to Sidebar and enjoy the great service and comfortable patio seating! I had the crab cake platter with fries and would order it again. At this point, we headed back to the hotel to get ready for our evening event but I did further research for you on other activities & restaurants to enjoy this evening.
In the afternoon, head out to Oatlands Historic House & Gardens for an opportunity to walk through centuries of history that define this historic mansion and surrounding land. For dinner afterwards, try King St. Oyster Bar, which came highly recommended online.
Day 3:
On the morning of your departure, carve out some time to stop by bkd Bagels. We had the honey bee oat cold brew (can you tell I have a penchant for honey drinks?) and a spicy everything bagel with scallion cream cheese. This combo was worth the trip to Leesburg in itself — so freaking good!
Since we had an evening flight home, we had time to check out the Steven F. Udvar-Hazy Center, an aviation museum well-worth visiting if you have the time. This museum is filled with all kinds of old planes and space shuttles from various points in history. Even if you don’t enjoy all the reading at museums, there is so much to see here!
Our last stop before returning the rental car and starting the journey back home was Cooper’s Hawk, a chain restaurant with delicious appetizers and an extensive wine list.
Final Thoughts
Leesburg was the kind of unexpected weekend away we needed in our life. So many of our trips are planned to the brim, but here we spontaneously created a weekend itinerary that felt comfortably mixed of activity and relaxation. Not to mention, it’s picturesque with nature dotted throughout and history seeping through every corner.
Whether you’re looking for a relaxing weekend away or a chance to learn and explore a historic area, you need to have Leesburg on your list!
Travel Links
Here, I’m linking travel items that I love (and personally use) for a quick weekend trip:
Crossbody bag: My favorite crossbody bag. I bought it for the sheer space it provides as a travel purse but I use it regularly when running errands back home too. Easily fits my Kindle, passport, wallet, and all the little doodads I like carrying with me.
Vera Bradley backpack: This backpack has so many pockets and is great for a weekend bag. I have never had a problem packing for a 2-night stay at a warm weather destination in this backpack!
Foldie: Another great bag for weekend travel and my husband’s choice for any trip. There is a zipper at the bottom to expand the bag if you need more space!
Steamer: I love traveling with a steamer, and this one works so well. Not super compact but I usually have my husband throw it in his bag since he packs so minimally.
Toiletry containers: these or these are good options. I own and use both for different products.
For anything else you’d like to see in future itineraries, please leave me a comment below!