If you have walked down Washington Street this summer, you have probably heard the old Fun Shop before you noticed anything had changed inside it. Saws. Hammers. The particular racket of a building being gutted down to a blank slate. A previous developer's plan to put a steakhouse in that space stalled out years ago and never recovered. What is going in there now is not a steakhouse, and it is not really a single restaurant either. It is the first piece of something that changes what going out to eat in Middleburg actually means.
What's Actually Going Into the Old Fun Shop
The space next to the post office is becoming La Caccia, an Italian restaurant from developer Kevin Ash, whose Chase Club project is building parallel outposts in Leesburg and Warrenton at the same time. The old Fun Shop building measures roughly 15,000 square feet, a little more than the floor area of the Middleburg Safeway, which gives some sense of the scale Ash is working with. The plan for the site includes La Caccia downstairs, a private members' club upstairs with two bars, an Italian café in the historic house on the property that will run breakfast through dinner, and what Ash describes as a speakeasy tucked behind the café. The three single-family houses already on the lot are being renovated rather than removed, a detail that came at the request of Middleburg Mayor Bridge Littleton.
La Caccia is not a standalone bet. It is one piece of a coordinated buildout that also includes the Huntōn in Leesburg, whose name La Caccia is meant to echo, and a French brasserie in Warrenton built in the mold of a lively, unpretentious neighborhood spot rather than a formal dining room. Members of the Chase Club get access to all three locations plus roughly 70 social events a year, from fly fishing trips to catered winery picnics. Ash, who also works as a stonemason, land planner, and restoration specialist, sums up his own role in three words: "I manage risk." That risk management now extends to an early conversation between the Chase Club and Salamander Resort about some level of reciprocity between the two, which would mean Middleburg's most established luxury address and its newest one start sharing members rather than competing for them.
The Three Lanes Middleburg Diners Already Know
Before this year, eating out in Middleburg meant picking one of two lanes. There was the estate and resort tier, built around an overnight stay or a special occasion, and there was the walkable tavern tier clustered along Washington and Madison Streets for a casual dinner or a drink after work. The Chase Club is introducing a third lane that did not exist in either form: a membership tier that ties Middleburg to two other towns.
Tier | What it looks like | Where you'll find it |
|---|---|---|
Estate and resort dining | Reservation-driven, often paired with an overnight stay or spa visit | Harriman's at Salamander Resort, Grayson's at Goodstone Inn |
Walkable town taverns | Casual, walk-in, clustered on Washington and Madison Streets | Red Fox Inn & Tavern, King Street Oyster Bar, Red Horse Tavern |
The new networked tier | Membership-based, shared across three towns | La Caccia and the Chase Club, linked to the Huntōn in Leesburg and a brasserie in Warrenton |
The distinction matters for anyone deciding where to spend a Friday night. The first two lanes have always been local decisions, tied to a single building or a single street. The third lane is regional by design. A Chase Club membership bought in Middleburg buys a table in Leesburg and Warrenton too, which is a different proposition than anything the town's dining scene has offered before.
Grayson's Shows the Estate Tier Isn't Standing Still Either
The Chase Club is not the only sign that Middleburg's food scene is in motion. Goodstone Inn, the historic estate on Snake Hill Road, opened its own new restaurant this summer. Grayson's is named after the property's resident llama and runs breakfast, lunch, dinner, weekend brunch, and a bar menu built around what the estate's own farm produces that week. It is a reminder that the estate and resort tier is not a fixed category waiting to be disrupted by whatever the Chase Club builds. Goodstone is investing in its own dining identity at the same time, which means the fall calendar has two parallel stories rather than one developer reshaping the town on his own.
What Else Is on the Calendar Before the Leaves Turn
The town's rhythm this season is not just about restaurants. The Middleburg Business and Professional Association's Summer Sidewalk Sale wrapped up the first weekend of August, timed to coincide with Virginia's tax relief weekend, and it is worth knowing about even after the fact because it tells you the town still runs on a predictable annual clock that locals can plan around next year.
What is still ahead:
- Middleburg's 5th annual Oktoberfest lands on South Madison and Federal Streets on September 19, with a beer garden and a local artist market running alongside it.
- The Virginia Fall Race returns to Glenwood Park on October 10, the same grounds that host the town's spring steeplechase.
- The Middleburg Film Festival runs October 15 through 18, four days of programming that fills the town's inns and restaurants well past the usual weekend crowd.
That last date is worth watching closely if you are curious whether La Caccia opens on schedule. A fall opening puts the restaurant's debut somewhere in the same window as the Film Festival, which means the first real stress test for the new space could be one of the busiest weekends the town sees all year.
What It Means If You Already Call Middleburg Home
The short version is that dining out here used to be a choice between two fixed categories, and neither category ever really talked to the other. An estate dinner at Goodstone or Salamander was its own occasion. A night at Red Fox or King Street Oyster Bar was a different, more casual one. What is arriving this fall is a third option built specifically to connect Middleburg to towns you might already be driving to anyway. If the Salamander and Chase Club conversation about reciprocity moves forward, even the estate tier stops being a closed loop.
None of this changes what makes Middleburg Middleburg. The Red Fox Inn is not going anywhere, and neither is the horse and hunt calendar that has defined the town for three centuries. But the map of where you can eat, and who you can eat there with, just got a new node that reaches past the town line on purpose. That is worth knowing whether you are deciding where to take out-of-town guests during Film Festival weekend or just trying to figure out what the construction noise on Washington Street has actually been about.
If you are watching Middleburg from a little further out, whether you already own here and are curious what these changes mean for the town's long-term draw, or you are weighing a move to hunt country yourself, Celeste Linthicum follows this market closely enough to talk through what it actually means for your specific situation. Schedule a consultation whenever you are ready to talk it through.