Walk past the old Fun Shop on Washington Street this month and you'll hear it before you see it: hammering behind plywood, a generator running somewhere inside a building that's been dark for longer than most people in town can easily place. For years it sat as retail space nobody quite knew what to do with. Before that, a different developer had plans for a steakhouse there, plans that stalled and eventually fell through entirely. Now there's activity again, and by fall it will reopen as something else entirely.
A mile and a half away, at Goodstone Inn on Snake Hill Road, a different kind of change already happened. The dining room longtime visitors knew as the Bistro, or sometimes the Conservatory, has a new name, a new menu, and a new reason to book a table. It opened this past June.
Two restaurant stories, both landing in Middleburg the same year. Neither one is actually a story about a new restaurant. Look closely and they're the same story told twice: nothing new got built. Something old changed hands.
The Building Everyone Still Calls "The Fun Shop"
The property next to the Post Office is 15,000 square feet, sizable enough that it's roughly a fifth larger than the Middleburg Safeway. Developer Kevin Ash bought it after the previous steakhouse concept collapsed, and by his own account, the building needed to be gutted before anything new could go in. He's described the process to Fauquier Now as starting from a blank slate. That was back in April, when the restaurant's name and cuisine were still undecided.
By July, the plan had a name: La Caccia, Italian for "the hunt," a nod that echoes The Hunton, Ash's restaurant in downtown Leesburg. The Georgetowner reported that the historic house on the property will become an Italian cafe serving breakfast, lunch, and dinner, with a members-only club called The Chase upstairs, complete with what Ash calls two proper bars and a speakeasy tucked behind the cafe.
Ash has been candid about what made this take so long. Asked about the pace of the project, he pointed to the town's own process:
"Time kills deals."
He's also drawn a direct comparison to Fauquier's county seat, telling the Georgetowner that Warrenton is "super-proactive to get downtown development going," a contrast he raised while describing Middleburg's slower path, including a stretch when the town manager's position sat vacant. Whatever the reason, the math is simple: a building this size, in a town this small, doesn't come open often. When one finally does, it takes a developer already building hotels and clubs elsewhere to make it pencil out.
A Mile Down Snake Hill Road, the Same Story in Reverse
Goodstone Inn didn't need a vacant building. It already had a restaurant, on a 265-acre working estate with its own gardens and farm. What it did was retire an old identity and build a new one inside the same walls.
Grayson's, announced by Goodstone in June, is named for the estate's resident llama, a detail that only makes sense once you understand the restaurant's whole premise: an estate-driven menu built around what the farm actually produces that week. General manager Michael Smith framed it as an attempt to tell the story of the property itself, from the ingredients on the plate to the hospitality around the table. The restaurant now runs breakfast daily, lunch and brunch service, and dinner nightly, with a bar menu added to the lineup.
None of that required new construction. It required a decision that the dining room deserved a name of its own, one that pointed to the farm rather than to the inn's general reputation.
Same Space, New Name
| Location | What It Was | What It's Becoming | Status as of August 2026 |
|---|---|---|---|
| Washington Street, beside the Post Office | Vacant retail (the "Fun Shop"), a stalled steakhouse concept before that | La Caccia (Italian cafe, breakfast/lunch/dinner) with The Chase Club upstairs | Under construction, opening this fall |
| 36205 Snake Hill Road, Goodstone Inn | The estate's longstanding dining room, known to regulars as the Bistro or the Conservatory | Grayson's, an estate-driven restaurant named for the farm's resident llama | Open now, launched June 2026 |
Why the Village Grows Sideways, Not Outward
Neither project added square footage to Middleburg. One reused a building that had already failed once under a different concept. The other reused a kitchen and dining room that had operated under two prior names before this one. That's not a coincidence specific to these two projects. It's close to the only way commercial change happens in a town this size.
Middleburg doesn't have vacant lots waiting for new construction on its main commercial block. What it has is a small, fixed set of structures that occasionally change hands or change concepts. When that happens, it tends to happen all at once and it tends to take a while to arrive, because there's no shortcut around the number of buildings involved. Ash's own account of the timeline, from an undetermined restaurant concept in April to a named project with renderings by July, shows how much work happens before anything visible starts on the street. Goodstone's rename happened faster, but it was still built on infrastructure that had existed under other names for years.
If you've lived here a while, you already do this without thinking about it: you call a building by what it used to be. The old Fun Shop. The Bistro at Goodstone. That habit isn't nostalgia so much as an accurate map of how the place actually works. New identities arrive. The buildings underneath them mostly don't.
What to Watch This Fall
La Caccia doesn't have a firm opening date yet, only "this fall," per the most recent reporting. Given that Ash's Clay Construction crew is still finishing buildout on both the restaurant and the club level, and given his own comments about how long these projects tend to take once the town's review process is involved, treat any specific date you hear secondhand with some skepticism until the town or the restaurant confirms it directly.
Grayson's, by contrast, is already open and taking reservations, with breakfast starting at 8 a.m. daily and dinner service running into the evening seven nights a week.
If the pattern holds, the next building to change hands on Washington Street won't be a new one either. It will be something else you already know by its old name, waiting for someone with the patience to start from a blank slate.
Have questions about what's happening on a specific block or property in Middleburg, or curious how changes like these tend to ripple through the rest of the village? Bretton Molenaar has spent years watching how this town actually moves. Let's Connect.
