Why would a private social club with $2,500 annual dues need another Virginia address in a town where the sidewalks empty out well before 9 p.m.?
That is the question sitting behind the scaffolding on Washington Street, where, as The Georgetowner reported, developer Kevin Ash has spent 2026 gutting the old Fun Shop building. Middleburg's fall calendar looks the way it always has on paper: a polo classic in September, an Oktoberfest that closes two downtown blocks, a steeplechase every October that has run since Eisenhower was in office. Those events are built for people who drive in. What is going up a block from the post office is built for people who already live close enough to walk.
What's Actually Going Up Behind the Scaffolding
The Fun Shop was 15,000 square feet of empty retail space, larger than the Middleburg Safeway, which runs 12,500 square feet. Ash and his team at Clay Construction had to clear the whole thing down to a shell before starting over. What comes back will be an Italian restaurant called La Caccia, Italian for "the hunt," a name that echoes his Leesburg restaurant, the Huntōn. The historic house on the property becomes an Italian café serving breakfast, lunch and dinner, with a speakeasy tucked behind it. Reporting on the buildout notes the speakeasy already has its ABC license.
Three single-family houses on the site are being renovated at the request of Middleburg's mayor, Bridge Littleton. Architect Michael Wood of Woodworks Architects has been walking the Historic District Review Committee through the plans, and one detail stands out: a rooftop garden, which would be the first of its kind in Middleburg. The idea was spurred directly by how popular the rooftop at Ash's Hotel Burg in Leesburg turned out to be. As of March 2026, reporting on the project put the target at a fall 2026 opening, with the restaurant's name and speakeasy still being finalized at the time.
A Club Built on Reciprocity, Not Just Exclusivity
Upstairs from La Caccia will be another location of The Chase, Ash's members-only social club. The math on this only makes sense once you see how the other locations work. In Leesburg, The Chase already has 450 members. In Warrenton, where Ash is also developing the Warren Green, he has said the club there could hold between 300 and 400. Annual dues run $2,500 and include reciprocity across all three locations, which means a member who joins in one town can use the others.
Ash has pushed back on the idea that a private club sits awkwardly in a small hunt-country town. Fauquier Now quoted Ash saying, "it's no different than joining the fitness club." The Georgetowner reported that Ash had said the Middleburg location was working out some form of reciprocity with Salamander Resort, describing it as "a very positive relationship about how the Salamander and the Chase Club could work together in the future." Read that plainly and it means someone with a Salamander spa membership could, in theory, be upstairs at the Chase bar on a Wednesday night. That is a different kind of infrastructure than a steeplechase. It is not designed to pull in a crowd for one Saturday a year. It is designed to give people who are already local somewhere to go on the nights nothing else is happening.
For a sense of what that membership experience actually includes, the Leesburg location offers more than 50 curated events a year, among them monthly wine tastings and talks hosted by Orvis, plus access to a rooftop bar, a speakeasy, and coworking space. Nearly half of its founding members are women. None of that programming is specific to Middleburg yet, but it is the model Ash is exporting.
The Season Everyone Already Knows
None of this replaces the fall calendar Middleburg has run for generations. That calendar already came through once last month. The National Sporting Library & Museum held its Polo Classic on September 13, with proceeds supporting the museum's work preserving equestrian and field-sport literature and art. Middleburg's own Oktoberfest followed on September 19, its sixth year running, closing South Madison and Federal Streets to traffic for biergartens, German food and live music.
What is still ahead is bigger. On October 10, Glenwood Park hosts the 72nd running of the Virginia Fall Races, sanctioned by the National Steeplechase Association. Glenwood Park itself is the oldest continuous racecourse in Virginia, established in 1911 on 150 acres that are now protected in perpetuity through a conservation easement. Proceeds from the race day benefit the Inova Hospital Foundation and the Glenwood Park Trust. Later in the season, the Byrne Gallery marks its 30th anniversary with an exhibition of oil and enamel paintings by Yuri Gorbachev running through November and December, his 22nd consecutive show with the gallery.
That is the visitor-facing Middleburg, the one built around a handful of marquee weekends that draw crowds from well outside town. It has not gone anywhere and it is not competing with what is happening on Washington Street. It is running in parallel.
Two Economies, Running at the Same Time
The tell is in what else opened this year, quietly, with none of the fanfare of a steeplechase. Goodstone Inn's new restaurant, Grayson's, opened in June, named after the estate's resident llama, serving farm-to-table breakfast, lunch, dinner, weekend brunch and a bar menu built around the daily rhythm of a working farm rather than a special-occasion calendar. Granted Wellbeing, a new Ayurveda-focused wellness space founded by Maggie Grant, held its grand opening on September 12 at 15 South Madison Street, offering infrared sauna sessions, color therapy and warm oil scalp massage. Neither of these businesses is scheduling around a race weekend. Both are built for a Tuesday.
Put the Fun Shop corner next to Grayson's breakfast service and Granted Wellbeing's sauna bookings and a pattern holds. Someone is betting that Middleburg's population of everyday residents, not just its weekend visitors, is large enough and settled enough to support a members' club, a full-service Italian café, and a wellness studio that all depend on repeat, weeknight business rather than a single big Saturday. The fall calendar proves the town can still pull a crowd once or twice a month. The Fun Shop corner is a bet that the town can also fill a dining room on a Wednesday, which is a much harder thing to prove and a much more interesting one if it works.
If you are weighing what a shift like this means for property values, foot traffic, or the long-term character of a town you already call home, that is exactly the kind of on-the-ground read LifeStyle via Real Estate tracks across Middleburg and the rest of Northern Virginia's hunt country. Schedule a consultation with Cheryl Folmer if you want to talk through what these changes could mean for your own plans.
