“Tring-tring – On your left!” my son yells, ringing his bike bell and pedaling just a little harder to pass a jogger. I echo a polite “on your left!” and catch the jogger raising a hand in greeting out of the corner of my eye. The trail smells amazing; the blooming wild honeysuckle spreads a sweet scent that makes not just us, but the butterflies and bumblebees want to slow down and linger.
Growing up in Belgium, a bicycle isn’t just a piece of sports equipment; it’s an extension of yourself. You bike to the bakery, you bike to school, you bike to meet friends. It’s about moving through daily life at your own pace. When we moved to the US, we quickly realized that the car is king. Safely navigating a town on two wheels isn’t always a given. But Leesburg is different. Here, we found a rare slice of that pedal-powered European freedom.
- A Green Tunnel to Downtown
- Coffee Stop: Between Locals and Lattes
- A Hidden Boutique with European Flair
- Rocking Chairs on the Porch and Pistachio Lattes
- European Charm Meets an American Movie Set
- Parakeets, Dolly Parton and Chinaware
- A Jungle Behind a Book Cover
- Secret Courtyards and Fairy-Tale Patios
- Sweet Summer Evening Cravings
- Practical Tips: Exploring Downtown Leesburg (With or Without a Stroller)
- A Home Away from Home
A Green Tunnel to Downtown
Summers in Virginia can be sweltering, but you can always find a cool breeze on the Washington and Old Dominion trail (W&OD). A large part of this paved path is hugged by a canopy of old trees. It forms a lush, green tunnel to bike through, and when there’s a gentle breeze, it’s absolutely perfect.
The W&OD trail is a former railroad line transformed into a 45-mile-long walking and biking path, stretching from Purcellville all the way to Shirlington. But the best part? It runs right through our hometown of Leesburg.
Oncoming cyclists always look pleasantly surprised when they see another child sitting in the back,
something you rarely see in the US.
With Hubby being an avid cyclist, this trail was one of the deciding factors in putting down roots here. We love ditching the car and hopping on our bikes. Having the freedom to safely pedal into the historic downtown area in under ten minutes is a true luxury. It allows us to hold onto our European ‘slow travel’ lifestyle right in our American backyard.
Coffee Stop: Between Locals and Lattes
During our W&OD rides, we usually hop off near South King Street. It’s a spot that still breathes the trail’s railroad history.
The bridge crossing the small Town Branch is painted with a beautiful mural that makes it look exactly like a train. Right next to it, is the ‘Stationmaster Pavilion’, a charming nod to the old Leesburg train station that once stood nearby.
Our first stop after parking the bikes? Goosecup! First and foremost a stellar coffee shop, but equally great for a glass of wine on the patio. Since it’s located right on the trail, it’s one of the few places where you can easily park your bike.
It can be a challenge to go on these sidewalks with a stroller.
If you plan on exploring the rest of downtown, I highly recommend leaving your two-wheeler at Goosecup. Not only do you have a fairly steep climb ahead of you, but the bike paths end… And the sidewalks, while charming, are narrow. The historic houses with their authentic front steps leave little room to properly park a bike (or maneuver a stroller).
and at the coffee bar.
Goosecup has cozy seating both inside and out, and is incredibly kid-friendly. You’ll find cute little tables and chairs, a basket with books and toys, a kids’ menu, and even a handy step stool in the restrooms.
They are open seven days a week, though somehow I always crave a coffee exactly on a Tuesday after school: the one day they close early. Thankfully, they make up for it by staying open until 10 PM on weekends!
A Hidden Boutique with European Flair
While you’re at Goosecup, don’t forget to look up! Located in the same building, accessible via a side door and (unfortunately, only) a long flight of stairs, you’ll find Mon Chouchou. It’s a lovely children’s clothing boutique that gives off a distinct European vibe through its style and quality. Although it’s hard to miss the American notes either.
The collection is a bit more exclusive and leans toward the higher end, but the items are truly beautiful!
Keep the stairs in mind, as it’s not ideal with a stroller. Additionally, take note of their somewhat limited hours (typically 11 AM to 5 PM). Tip: While you browse the racks, the kids can perfectly entertain themselves at the small table equipped with children’s books and magna tiles.
Rocking Chairs on the Porch and Pistachio Lattes
While the rocking chairs are always a favorite,
the seats around the fire pit are just as cozy.
Of course, there are plenty of other options for a great cup of coffee in Leesburg. Sometimes you’ll find us gently rocking in a chair on the porch of Second Nature Coffee Co., or tucked away among the greenery at Shake & Bops Botanical Coffee.
Shake & Bops Botanical Coffee has a small courtyard where you can also sit outside, although we prefer sitting inside among the bamboo and rattan. There is also some reading material and colored pencils provided for the children. You can also get ice cream here in the summer!
Though I have to admit, my absolute favorite Leesburg coffee is actually just outside of downtown. I simply cannot stay away from the pistachio mocha latte at SR Coffee.
Unfortunately, this place is less child-friendly. That said, even my toddler can’t look away from Bob Ross’ painting techniques playing on repeat on the TV here.
European Charm Meets an American Movie Set
South King Street to
the Townhall and the
public ‘Townhall Garage’.
After coffee, we love to stroll down South King Street. This is where the unique atmosphere of downtown Leesburg truly hits you.
On one hand, it’s incredibly charming. The cozy vibe, narrow alleyways, and weathered brick walls instantly transport my mind back to Europe. Specifically, they remind me of the historic streets of my hometown, Ghent.(Belgium).
But the moment I look up at those quintessential American facades, with their inviting wooden porches and classic signs, I suddenly feel like the main character in a Hollywood movie.
It’s a magical contrast that never gets old.
Parakeets, Dolly Parton and Chinaware
You’ll find countless boutiques and quirky shops here, but we almost always pop into Brick and Mortar. The kids love saying hi to the parakeets in their cage, while I usually end up trying on a pair of sunglasses or a Stetson.
We also rarely pass up the Global Local (located nearby on the corner of Wirt St. SW and Loudoun St. SW). The store has fairtrade products and unique finds from local makers in Leesburg and around the world.
Bonus: the Global Local is located right next to the previously mentioned Shake & Bops Botanical Coffee.
Are you looking for an original gift with a hilarious quote or cute tableware, or are you secretly a fan of Dolly Parton? Then you can certainly indulge yourself at these stores.
A Jungle Behind a Book Cover
Tucked away on a side street, West Market Street, you’ll find our favorite bookstore: Birch Tree Books & Plants. You have to climb a few steps to get in (so it’s best to leave the stroller outside), but once inside, you wander through a maze of cozy little rooms filled with stories. It’s a bit of a shame it’s not entirely stroller accessible, because the kids’ section is fantastic.
And the best part is at the very back: past the books, you step into the plant section. It feels like walking into a mini-jungle surrounded by lush greenery. From tiny succulents to impressive trailing plants, you’re guaranteed to find the perfect green addition for your bookshelf.
Secret Courtyards and Fairy-Tale Patios
Inside, it has a cozy vibe among the old shoes.
A narrow alleyway leads you outside to an enchanting patio
When hunger strikes, we almost always end up taking the kids to Shoe’s Cup and Cork or Sidebar.
Why?
Because they both feature hidden patios (another detail that beautifully mirrors the courtyards of historic European cities).
At Shoe’s Cup and Cork, it feels like a little secret mission walking down the narrow alley to reach the patio.
It’s always a delightful surprise to emerge into the deep garden strung with cozy lights. The inside is just as captivating! There’s so much to take in: the quirky decor makes it impossible to forget that the building used to be a cobbler’s shop.
Sidebar consists of several interconnected historic buildings. Besides the restaurant and coffee shop (where I also get my fresh sourdough bread from The Local Loaf), a staircase leads up to Nightshift, a cocktail bar. Way in the back on the patio, you’ll stumble upon The Docket. The Docket is a tiny cottage where you can order drinks and settle into comfortable lounge seating. The whole maze of passageways, historic brick walls, and different patio levels creates a mysterious, fairy-tale vibe that the kids absolutely love exploring.
at the back of Sidebar’s patio.
It features a cute bar inside and an adjoining patio area
with comfortable lounge seating.
Personally, I’m a big fan of the menu at Sidebar. The food is just a little more refined and lighter than at Shoe’s Cup and Cork.
To help you plan your visit, keep these hours in mind:
- Sidebar: Open daily for lunch and dinner (with breakfast and brunch reserved for weekends).
- Shoe’s Cup and Cork: Closed on Tuesdays and Wednesdays. However, on open weekdays, you can grab breakfast, lunch, and dinner. They also offer an all-day brunch on Sundays!
- Bonus: Both spots host fantastic weekday happy hours.
Sweet Summer Evening Cravings
And then: dessert! You are spoiled for choice in Leesburg.
Adirondack Chairs & Soft Serve at Gruto’s
The kids are obsessed with the soft serve at Gruto’s, even though we have to leave the stroller at the bottom of the stairs again. Afterward, there’s nothing better than enjoying your cone in one of the bright yellow Adirondack chairs next to the shop.
Macarons & Secret Mouse Doors at Mocatina’s
Mocatina’s is another spot where their eyes widen. The French-inspired interior is gorgeous, but the kids always sprint straight for the tiny “mouse door” hidden at the bottom of the stairs. Downstairs, you can score small pastries or artisanal ice cream from Maryland’s South Mountain Creamery, while upstairs hosts a full high tea. Though honestly, Mocatina’s is most famous for their fantastic macarons!
Gelato & Speakeasy Vibes at Gogo’s
Still, my ultimate favorite is Gogo’s. It’s a tiny spot you’d easily walk right past if you didn’t know it was there. Inside, there’s just enough room to order, after which we settle on the bench against the facade with flavors like ‘Shot in the dark’ (espresso gelato with dark chocolate stracciatella) or ‘GoGoGoma’ (black sesame). Yum!
Gogo’s is currently closed for renovations, but should be ready to cool us down during the hottest days of the year. You can still sneak through Gogo’s into Tarbender, a secret speakeasy bar… but we’ll save that one for a date night without the kids.
Gogo’s also just openend a new apertivo bar Piazza Di Gogo’s, just around the corner! It’s located inside another great brunch spot named Buford’s Biscuits. In fact, they share the space, with the aperitivo bar opening right when Buford’s closes.
What makes Leesburg extra cozy is that places like Gogo’s and many other ice cream shops stay open late on weekends. It’s perfect for stepping out into a warm summer evening to satisfy a late-night sweet tooth.
Practical Tips: Exploring Downtown Leesburg (With or Without a Stroller)
Where is Leesburg?
Leesburg is located in Northern Virginia, just an hour’s drive from Washington D.C.. With nearly 50,000 residents, it’s a vibrant town of considerable size. Situated at the foothills of the easternmost ridge of the Blue Ridge Mountains, the area offers a beautiful blend of nature and history.
You’ll find not only rolling wine valleys and a charming, historic downtown, but also a more modern side. For instance, you can shop to your heart’s content at the Leesburg Outlets.
you can actually sit in some of the vintage planes.
The town even has its own airport for small planes. If you happen to be in the area during the fall, they host an annual free airshow here. It’s usually on the last Saturday of September.
Add the famous W&OD trail that cuts right through town to the mix, and it’s easy to see why Leesburg is a place with many faces. From peaceful nature to bustling shopping streets, there truly is something for everyone!
Free Parking
Not arriving by bike?
If you’re exploring Leesburg by car, you’ll find several public, covered parking garages right in the center (we usually opt for the Townhall Garage).
A fantastic bonus: parking here is completely free on weekends and weekday evenings. The gates also stay open during special holidays or in the festive season leading up to Christmas.
Close to the W&OD trail and coffee bar Goosecup, you will also find the free street parking Liberty Street Parking. By the way, a beautiful mural of Leesburg can be found there as well!
it’s easy to see just how steep some of
the streets in downtown Leesburg really are.
Stroller-Friendly, With Some Climbing
The sidewalks in the historic center are often narrow, and you’ll encounter a few steep sections.
Luckily, Leesburg has recently added some new, smoother pavement in areas. Despite the small climbs and tight squeezes, you can generally navigate the town fine with a stroller, as long as you’re not in a rush.
The Restroom Struggle: Good to Know!
located right behind the Town Hall
and next to the Town Hall Garage.
A crucial detail, especially when traveling with young kids: there are virtually no public restrooms in downtown Leesburg (not even in the parking garages).
The downtown buildings are centuries old. Consequently, it’s simply too difficult for many local businesses to provide public facilities. You’ll frequently spot ‘no public restroom’ signs. Especially in the evenings and on weekends when it gets wonderfully busy, restaurants understandably don’t want non-paying customers slipping in just to use the bathroom.
On the bright side, when restrooms are accessible, most are thankfully equipped with changing tables.
Tip: During the week, you can pop into Town Hall for clean, free restrooms. Though their hours are limited and they are usually closed on weekends. Plan those potty breaks strategically around your coffee or lunch stops!
Taking a Breather
Do little legs need a break, but you aren’t ready to sit down at a restaurant? Thankfully, the downtown area has a few lovely urban parks with benches and sometimes even picnic tables.
Mervin Jackson Park (located right next to the Townhall Garage, the Loudoun Museum, and Town Hall) is a wonderful spot, as is the green space right in front of the old courthouse. They are perfect places to catch your breath before continuing your walk.
By the way, anyone who would like to discover more historical spots in downtown Leesburg, can take a historical walking tour via the Leesburg app or this website. You will certainly come across the Elijah V. White House (see photo above) on this walk. It is especially worthwhile in the spring!
A Home Away from Home
With our purchases in the bike basket and the last remnants of ice cream still around the kids’ mouths, we cycle back home via the W&OD trail. I look back one more time. Leesburg might not have the centuries-old towers or cobblestones I am used to in Ghent, but just like ‘my Ghent’, Leesburg has an enormous amount of charm.
It is the unique combination of the Belgian-style patios, lush greenery, and that warm, typically American porch feeling that made us lose our hearts to this town.
You can stroll around here endlessly without a massive itinerary. The joy isn’t found in huge attractions, but in small discoveries: a hidden plant shop, a magical little mouse door at the bottom of the stairs, or simply swaying in a wooden rocking chair.
If your travels ever bring you to the Washington D.C. area, be sure to put this laid-back town full of European coziness and small-town charm on your list.
Are you a fan of small-town getaways? I’d love to hear which local gem instantly gave you that ‘coming home’ feeling. Let me know in the comments!
Also, for my local friends: yes, I know there are many many more great spots in Leesburg (especially in bustling downtown), it was hard to pick out our favorite spots! Perhaps you can share your favorite spot in downtown Leesburg to share with other readers?
