The Top Things to Do in Leesburg, VA and Loudoun County: Experience Historic Towns, Quaint Villages and Wine Country in Northern Virginia
If you’re a fan of picturesque colonial towns, winding tree-covered rural roads and rolling hills sprinkled with vineyards, then heading to Loudoun County is a must. With so many things to do in Leesburg, VA and the surrounding area, you won’t soon forget your visit to this part of Northern Virginia.
I have to say that when I was first headed to Northern Virginia, I wasn’t really sure what to expect. I had never visited the area before, but once I started to learn about the history of the region, its abundance of vineyards, and its rolling hills, it made me eager to see what it was all about.
I’d heard great stories about the state from Chris’s previous trip to Virginia. He loved his time visiting places like Virginia Beach and Richmond, but heading to Northern Virginia and Loudoun County was a new experience for both of us. As we hit the road and made our way to Loudoun County, the roads quickly became narrower, more winding, and honestly felt a lot like some of our recent experiences driving around Ireland and the United Kingdom. The quaint colonial towns and narrow, tree-covered roads make you feel like you’ve stepped back in time, or at the very least like you’ve found yourself in Europe on American soil.
The largest town in Loudoun County is Leesburg, making it a great place to base yourself, or at the very least enjoy the many things to do here. Of course, if you come to Loudoun County, it would be a shame to only visit Leesburg and miss out on the small town charm in other parts of the county. Let me help you plan for a visit to the region, and learn about the best things to do while you’re in town!
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The Unique Geography of Northern Virginia and Loudoun County
I have to be honest when I say that Virginia has always been a bit of a mystery to me. As a Canadian without much knowledge about the state, it was hard for me to picture where exactly we were headed in the United States. Upon taking a closer look at the map, I quickly realized why Northern Virginia felt particularly elusive to me: let’s just say the state lines in this part of the country don’t exactly follow a grid system.
It’s clear these lines were drawn in a different era. Northern Virginia is bordered by the Potomac River and Maryland to the east and the north, and West Virginia to the northwest. It kind of sits in its own little bubble in the northern part of the state, making a visit to Northern Virginia specifically feel a little more manageable to tackle.
Considering how far removed you feel from city life in Leesburg and Loudoun County, it’s shocking when you recognize that you’re only about 40 kilometres (or 25 miles) from Washington, D.C. This makes visiting the county accessible for travellers coming from elsewhere. In Chris’s and my case, we took the easy 1.5 hour flight with Porter Airlines from the Toronto Island Airport to Washington Dulles Airport, picked up our rental car, and were in Loudoun County a little more than an hour after we’d landed. This quick and easy trip makes visiting the historic towns of Loudoun County especially attainable for a fun weekend getaway, if you’re within a reasonable flight distance from D.C.
There are several beautiful counties in this part of Northern Virginia, but since Chris and I enjoyed our time in Loudoun the most, I want to focus on highlighting this region in this article. Aside from its largest town, Leesburg, the towns of Middleburg, Purcellville, and Waterford are lovely, too. Plus the area is home to more than 50 wineries, many of which are family-owned. As lovers of wine destinations, this was especially appealing to us.
Where to Stay in Loudoun County
When it comes to staying in the county, the most obvious choice would be an accommodation in Leesburg. There are several large hotel chains and boutique properties in town, along with a few resorts and spas.
Since Loudoun County is also home to several wineries and boutique, historic homes, I’d encourage you to push the envelope in terms of accommodation experiences and consider staying somewhere with a bit more of a story. Whether this is in Leesburg or another part of the county is your choice, but I always love a good experience stay.
Chris and I stayed in the Hummingbirds Hideaway Treehouse, a boutique property built by Waterford Reservations. It’s situated on the level of the tree canopy in a deciduous forest just outside the town of Waterford. It sleeps up to 6 guests, but I feel like 4 would be the most comfortable, and it offers opportunities to spot local wildlife—we woke up to see deer grazing on the forest floor—and hear the trees gently creaking throughout the day and at night. It was definitely a memorable stay, and I’d highly recommend it.
Whether you’re looking for a boutique accommodation or a larger hotel chain, you can bet on finding the best accommodation for the budget and experience you desire somewhere in the region. Feel free to take a look at the map below to help you choose the best place for you to stay on your trip.
The Top Things to Do in Leesburg
Let’s get into the heart of this article, shall we? Leesburg is chock full of history, delicious places to dine and beautiful natural gems to admire, so spending some time to visit this special part of the county is a must on your trip.
Indulge in Breakfast or Brunch
Starting a day of wandering is best with a good breakfast. Fortunately, Leesburg has some excellent places to stop for a delicious morning meal.
Chris and I set our sights on Leesburg Diner during our visit, which is in the historic downtown of Leesburg and has been open in its same location since 1865. Today it maintains a 1950s diner vibe, with friendly staff and delicious southern-style items on the menu, like biscuits and gravy and chicken and waffles.
A few other noteworthy places to stop at for a breakfast or lunch bite are South Street Under and Buford’s Biscuits. If you’re in the market for a later-in-the-day dining experience, you can’t go wrong with the famous King Street Oyster Bar’s original location.
Walk Around Historic Downtown Leesburg
As a town that was founded in 1758 by colonial settlers, the historic core of Leesburg reflects the complexity of its last 300 or so years. You’ll want to focus your time walking along King Street, Edwards Ferry Road, Market Street and Loudoun Street to get a full picture of its seamless blend of historic buildings and modern and trendy businesses.
Keep an eye out for some of the public murals you can find in town. Some highlights are the Discover the Charm mural in the Liberty Street parking lot, and the Journey to Freedom mural about Leesburg’s role in the Underground Railroad, located on the side of the Loudoun Museum.
It’s worth popping into a few shops while you’re walking around town, too, and you can visit George C. Marshall's Dodona Manor house, which was owned by the former Chief of Staff of the US Army in WWII.
Visit Morven Park
Located just outside of central Leesburg, Morven Park is an 18th century historic mansion. It was once the home of a former governor, and today it’s a museum and equestrian centre. The real highlight of visiting Morven Park is the access to its hiking and walking trails.
Since it’s surrounded by grassy knolls, its walking trails and paths will take you to pretty vantage points throughout the grounds, and offer you the opportunity to stretch your legs. Chris and I also caught sight of a young fox running around the park during our visit, which was incredibly cute to see.
Check Out A Nearby WinerY
As with most destinations in Loudoun County, it wouldn’t be a proper visit without popping into one of the local wineries. There is never a winery far away in this county, but visiting Stone Town Winery is an excellent choice. It’s less than a 15 minute drive from town, with an impressive tasting room and expansive grounds.
If you’re looking to visit a smaller winery in the area, Zephaniah Farm Vineyard and Willowcroft Farm Vineyards are good options.
Head to Red Rock Wilderness Regional Park
If you’re looking for a great place to take a walk in nature with beautiful views, Red Rock Park is just east of the city, situated on the Potomac River. It has easy walking trails that give you an extra dose of nature while you’re in the county.
Check Out the Washington & Old Dominion Trail
If you’re an avid cyclist, runner or walker, this reimagined rail trail is an excellent place to check out during your visit. The Washington & Old Dominion Trail is a converted rail trail that is completely paved, making for such a nice ride if you’re a fan of cycling, like we are. The complete trail is 72 kilometres (45 miles), and connects Loudoun County with the D.C. area.
A fun way to add a little something extra to your time in Loudoun County is to rent bikes from Pedego Electric Bikes in Leesburg. This makes for a great day spent cycling part of the trail, and visiting the town of Purcellville and the surrounding area.
Other Memorable Towns and Areas to Visit in Loudoun County
As much as Leesburg is an excellent place to visit, you can’t come to Loudoun County and only come to Leesburg. You’d simply be missing out on so much of what makes the county special. It’s in those in between moments on winding country roads that you really feel connected to this county, so I’d encourage you to branch out and plan to visit all or at least some of these other towns, too.
Purcellville, VA
Whether you end up biking from Leesburg along the Washington & Old Dominion Trail or you drive, Purcellville is a cute town in Loudoun County that encourages you to step back in time. This colonial town was settled in 1764, and the facades of some of its downtown storefronts on North 21st St. feel a bit like a Western movie set.
Highlights to check out while you’re in Purcellville include:
Having dinner at Magnolias at the Mill, a renovated grain mill in town offering a unique selection of hearty, rich dishes
Check out the exterior of the Purcellville Train Station. This building is kitty-corner to the mill, and marks the start and end point of the Washington & Old Dominion Trail along this historic, converted railway.
Pop into shops, cafes and restaurants along North 21st Street, between Main Street and the Washington & Old Dominion Trail
Visit a nearby winery, like Doukenie Winery, Sunset Hills Vineyard, Walsh Family Wine, or 8 Chains North
Middleburg, VA
Another charming village in Loudoun County (you’ll quickly learn that the whole county is just a charming place to be), Middleburg is slightly younger than Purcellville and Leesburg. It was founded in 1787 by colonial settlers, and is regarded as the “Nation’s Horse and Hunt Capital” because of its history of fox hunting and horse racing.
It’s often thought that Middleburg is Loudoun County’s prettiest village, and it has been the home to many a celebrity and millionaire over the years. Jackie Kennedy, Elizabeth Taylor and many more prominent figures have called Middleburg home. I can certainly see why—it’s an awfully charming place to be.
Here are a few things I’d recommend doing while you’re in town:
Visit for a meal or book a stay at the iconic Red Fox Inn. This stone inn and tavern was built in 1728, with connections to the Revolutionary and Civil Wars. It’s a beautiful property to visit today for a pint, a meal, or overnight.
Downtown Middleburg along Washington Street is an excellent place to go shopping and pop into local cafes and businesses. It’s lined with boutiques, antique shops and art galleries, making for a great place to wander around for a few hours.
Grab lunch at one of Middleburg’s many eateries. King Street Oyster Bar has a second location in town, and other local favourites like Bluewater Cocina and Red Horse Tavern are worth the visit, too.
Pop into a local winery while you’re in the area. Some local gems are 50 West Vineyards, Greenhill Winery & Vineyards, and Cana Vineyards and Winery.
Waterford, VA
Now I have to be completely honest when I say that it’s more than likely that Waterford, Virginia won’t be on your average recommendation list of places to visit in Loudoun County. When we had breakfast at the Leesburg Diner, our server in Leesburg had never even heard of Waterford.
This is not to say that Waterford isn’t worth visiting—it very much is—but the reason this village makes my list of recommended places is because the treehouse Chris and I stayed at was just outside of Waterford. And so this small, little known village of less than 300 residents became our home base during our time in the county.
The entire village of Waterford just so happens to be a National Historic Landmark, and as soon as you begin driving through its few streets and see the buildings that have been preserved here, it will become abundantly clear why. It was founded in 1733 by Quakers, and it grew to become the second largest town in the county prior to the American Civil War. It has a unique and lengthy history including stories of its residents being sympathizers to the United States to the north during the Civil War, so if you visit the town it’s definitely worth reading more about it.
While you’re in Waterford, I’d recommend that you:
Grab a coffee or small bite to eat at The Corner Store cafe.
Check out the exterior of the Waterford Grist Mill, which was built in 1818.
Wander around the few streets in town. It’s worth walking along Lower Main Street, 2nd Street and High Street to see its historic buildings like the Post Office and The Pink House.
Stay at the Hummingbirds Hideaway Treehouse, or another Waterford Reservations property.
Visit nearby More Better Restaurant & Beer Hall in Round Hill for lunch or dinner.
Bluemont, VA
Bluemont is another very small village in the county. Along with being part of Loudoun County, it’s also part of neighbouring Clarke and Jefferson counties, so it’s a good place to visit on your way towards more western parts of the state, like Winchester, the Luray Caverns, or if you’re leaving the county to return to the D.C. area.
Since the village of Bluemont itself is so small, the real focus when you’re here is on the local craft breweries and wineries, and experiencing the surrounding nature and views of the Blue Ridge Mountains. This is what I’d recommend doing while you’re in the area:
Stop at Bluemont Vineyard for incredible, panoramic views all the way out to the D.C. area on a clear day.
Visit Dirt Farm Brewery. It’s an excellent craft brewery to visit and is owned by the same team as Bluemont. It also offers exceptional views of the area.
Go for a hike in the Blue Ridge Mountains at Raven Rocks.
Savouring a Quiet Pace in Loudoun County
I have to say that the true cherry on top of my trip to Loudoun County was taking in the views from Bluemont Vineyard. I could have sat here for hours watching the clouds and distant storms move across the open skies. Admiring the county from this vantage point with its vineyards, countless towns and villages and winding roads really helped me appreciate just how special this corner of Northern Virginia is.
No matter where your time in Loudoun County takes you, it is guaranteed to bring you peace. Whether you’re prioritizing time spent outdoors, sipping on wine, learning about the region’s history, arts and culture, or a little bit of everything, a trip to Loudoun County will be one for the books.
I want to thank Virginia Tourism and Visit NoVA for hosting me as media for this trip to Loudoun County. All opinions expressed are completely my own.
Bri Mitchell
Bri Mitchell is a travel writer and content creator from Toronto, Ontario. She loves to highlight all things nature, food, wellness, sustainability and adventure in her work. Bri writes and shares her travel experiences from across Canada, the United States and around the world on Instagram and TikTok (@brimitchelltravels), and in her articles for travelingmitch, Ultimate Ontario, and We Explore Canada.