We’ve all been there — we’ve all had “that” weekend:

You were busy at work, and you just didn’t get around to planning out your precious days off like you wanted to. But, you don’t want another Saturday to go by where you “just chilled...” (AKA stayed home and half-watched TV, half-scrolled through your phone for approximately 5 hours.)

But, guess what? You can forget weekend-planning stress and still make the most of your free time. Because in super cute, super walkable downtown Leesburg, you don’t even need an itinerary to have an adventure! Sometimes, nothing beats hanging with a pal and simply seeing where the town takes you, without too many plans or expectations dictating your moves. 

So, just text your bestie to meet you in downtown Leesburg for the day. Because you’re spontaneous like that! You’re free-spirited, dang it! And it’s time to live out your secret travel blogger fantasy!

Leesburg is one of our favorite towns for these kind of planned-unplanned days out because of how easy it is to find inspiration around every corner.

Here are some of Leesburg quirks you’ll love discovering wherever you wander:

  • Converted architectural gems, like:
    • Cocina on Market, a renovated building from the 1870s that now functions as an authentic Mexican restaurant with a rooftop bar 
    • Lightfoot Restaurant, an upscale American restaurant housed within a refurbished, Romanesque-revival style former bank
  • Hidden oases, like: 
    • Shoes Cup and Cork, whose Secret Garden out back features outdoor dining alongside a Bocce Court 
    • SideBar, whose iconic plant-wall alleyway leads through to a twinkle-lit, cafe-style patio
  • Ever evolving scenes, like: 
    • 14 Loudoun, a popular bar that puts on over-the-top seasonal pop-ups, with themes ranging from “Summer Camp” to “Fa-La-La”
    • Tally Ho Theater, Loudoun's #1 rated music venue that features a constant stream of new acts and crowd favorites
  • Classic town staples, like:
    • Mom’s Apple Pie, farm-fresh, family-owned bakery with a cult following, founded in 1981 
    • China King, a Leesburg favorite which just celebrated its 30th anniversary!
  • Boutique shopping, like:
    • The Lucky Knot, a paradise for lovers of the preppy-chic look
    • Brick & Mortar, a haven for trendy gifts and knick-knacks that you never knew you needed
  • Historic sites all around, like:
  • Pockets of nature, like:
    • The Loudoun County Courthouse Green, a lovely lawn that makes for the perfect scenic picnic spot, right in the heart of downtown
    • Rust Nature Sanctuary, a tranquil nature preserve bordering downtown, with 68 acres of wooded trails, a charming historic center and a garden to explore
  • Niche-interest destinations, like: 
    • BITES Wine & Grilled Cheese Bar, with the most melt-in-your-mouth menu for cheese lovers
    • Very Virginia Shop, a store featuring only "Virginia's Finest Goodies and Gifts"
  • Public art, like: 
  • Breweries! In fact, six of them are all within a mile of distance of each another. Plus, when you visit this entire “Leesburg Cluster” with your LoCo Ale Trail Beer Passport, you’ll win a LoCo Ale Trail beer koozie from us!

Best of all...

Leesburg is one of those fun small towns where there always seems to be something going on.
Here are a few extra spots in and around the 'burg to consider visiting — hope this itinerary gives you all of the travel inspo and helps you decide to have an adventure!