Leesburg, VA
Leesburg, our home away from home (away from home)
Neha · 2026-10-16

After wrapping up in DC, we pretty much migrated to Leesburg, Virginia (only about 1 hr out from DC). Why, you ask? Well, because that’s where Varun was learning to fly! Yes, the insane overachiever is in the process of getting his private pilot license. Why, you ask (especially since there is no general aviation in Singapore’s tiny airspace)? Well, why not!
We were really lucky to stay at a couple of historic properties in Leesburg.
The first one was the cottage on Oakland Green Farm. The farm was established in 1730 (so it is older than the US!!) by a Quaker farmer, and it is still in the family (I believe the 9th generation)! That itself is an incredible feat! Sara (current owner) was super welcoming and gave us a tour of the original farmhouse (where she stays and about half a mile from the cottage where we stayed). The farmhouse still retained the original log structure, which melded into the stone section of the house, followed by the brick section – a living testament to the evolution of building materials over the years! And the inside was even more fascinating. A highlight was the wooden floorboards (uncommon for the time but put in by her family as they liked to dance) and a music box that plays music by twinging little indents on steel plates (think a giant version of small music boxes that we wind up in jewelry boxes etc)! The farm was even featured in some 250th celebration content: https://www.youtube.com/watch?v=SJhKtVFcr4k.
The second place we stayed was the Hill House, just a stone’s throw from Sara’s cottage. Another beautiful house with very homey/ grandmother home vibes. The centrepiece was a giant organ with so many buttons, so naturally the kids touched each and every single one. David (the owner of our cottage) invited us to visit his horses at his farm down the road. The boys absolutely fell in love with the animals – horses, Clementine (the dog), Route (the 3-month old calf named after Route 66 because her ear tag was coincidentally 66), and chickens (including 3 chicks!). On our last day, we got the peak horse experience by seeing the Loudoun Fairfax foxhunt kickoff! What is a foxhunt you ask? It's basically a competition where hounds and horses follow the scent of a fox and chase it down. No foxes are actually harmed as the troop makes quite a racket and no one's carrying weapons to hunt! The horses are judged on how well they do the various trail requirements, kind of like an obstacle course. We had never seen (and probably never will) so many hounds and horses gathered in one place. The excitement was palpable and everyone was dressed to the nines! What a treat!
Leesburg itself is a charming little town. Our properties were closer to Hamilton/ Purcellville, but we often went into Leesburg too. Our favourite café was Seven Teahouse (where we also did a matcha tasting) so that got a couple of repeat visits.
Caught a few movies on the “Tuesday $5 tickets” deal – Coyote vs ACME and Hanuman Ansh. Bumped into some old MBA friends (crazy small world) and visited this art supplies recycling shop, which was actually a very cool concept where people can donate extra/unfinished art supplies.
Visited some of the more family-friendly vineyards too!
The Quaker connection with Sara’s farm was fascinating. I didn’t really know much about the Quakers before this (except the oats LOL). Sara shared that the Quakers were basically kicked out of England and that's why they settled in the East Coast of the US (including William Penn, the founder of Pennsylvania, who was basically given the Pennsylvania land by King Charles II because the King had so much debt with William Penn). Learnt that the Quakers are a very open-minded bunch of people, and the reason they were kicked out was because they believed that people could directly commune with God without a priest/clergy intermediating. Yeah, that would certainly piss off the Crown. Interesting that some of America’s European foundations on the East Coast were that of a very free and respectful religion, and the Quakers went on to play very important roles in the abolitionist and women’s suffrage movements. I felt that the Quaker belief in an inner light that gives everyone direct access to God aligned with the non-dualist Vedanta viewpoint, that was a nice moment of coherence.
These bits of Virginia ended up becoming pretty significant for me over the time we spent there. My long (solo) walks on gravel paths were so peaceful and I had so many “aha” moments on random things that had been rattling around in my head. The old-ness of the land and how much of the history was living was quite astonishing. The connection to an older time was quite direct in some ways – we were listening to CDs in Sara’s home – and there is really something nourishing about old homes in the woods. I guess in Singapore everything is so new and constantly refreshed, so I really appreciated the old-ness.
There is also a deep peace in being totally alone and anonymous while on my walks. The occasional person or car would pass by and I’d wave hello, but that was really it. I had not previously realised how beautiful Virginia is, and am really glad we got enough time here to really soak it in. It will probably be one of the places we return to even though it is not a typical tourist destination.
Neha
One of four behind this road trip.