Upperville is easy to mistake for a village that never changes. Route 50 runs through it the way it did fifty years ago, the stone walls hold their line, and the calendar of horse shows and garden club meetings looks familiar from one decade to the next. That reading is half right.
Look closer at the addresses a resident actually visits in a given week, and 2026 has been a year of quiet turnover. The tavern on the east end reopened in March under new owners. The Wednesday market at Buchanan Hall is in its sixth season and has quietly grown into the village's most reliable weekly gathering. And the tasting room on Crenshaw Road is producing wine under a French-trained winemaker who trained in Bordeaux. None of it announces itself. All of it matters if you live here.
The Tavern Under New Hands
The Old Carr House at 9048 John S. Mosby Highway has been serving food since 2001, but it spent the tail end of last year closed for renovation. Historic local staple Hunter's Head Tavern in Upperville has reopened under new ownership and minor renovations. Formerly owned by Sandy Lerner, the founder of Cisco Systems who recently sold a large chunk of her Ayrshire Farm, Hunter's Head has had a 24-year run as a historic 18th-century gastropub in a building dating back to a 1750 log cabin. Noel and Alannah Sweeney, owners of Trinity Farm, purchased the property in late 2025 with a stated desire to preserve the restaurant as a centerpiece of the community.
The stewardship question was real. Noel Sweeney said he was afraid that no one would step up to buy it and it could possibly return to being a residence, which would leave a significant hole in the community. For a village whose main street counts its public rooms in single digits, losing the tavern would have been a structural loss, not a sentimental one.
Day-to-day operations are being run by a familiar name from down the road in Middleburg. The tavern's next chapter is being guided by Jarad Slipp, a Middleburg-based restaurateur and master sommelier known for Tremolo Bar and Knead Wine, who now oversees daily operations. Slipp says he has driven by Hunter's Head twice a day, every day, for ten years, and calls it iconic. At its core, Hunter's Head remains a pub, one that now leans more deliberately into its British roots. Slipp, who previously worked in London under Gordon Ramsay, is refining the menu while keeping it grounded in tradition, and guests will find familiar options alongside a Sunday roast served all day. The beer list still runs to Guinness and Miller Lite. The wine list does not.
One meaningful practical change: the Ayrshire Farm supply chain that defined the kitchen for two decades is no longer the operating premise. Under Lerner's ownership, Hunter's Head was the first certified organic, sustainable and Certified Humane restaurant in Virginia, serving products raised on Ayrshire Farm. A separate sale of the majority of the farm means the two entities are no longer connected. The Sweeneys' own Trinity Farm sits adjacent, so the sourcing story stays local, but the specific certifications that defined the old menu are a chapter that has closed.
Wednesdays at Buchanan Hall
If the tavern is the village's evening anchor, the Wednesday market is its late-afternoon one. The Buchanan Hall Community Market returned for its 6th season on Wednesday, May 20, 2026, and runs weekly through October from 4:30 to 7:30 PM on the historic grounds of Buchanan Hall in Upperville. Each week features a curated mix of hyper-local vendors offering fresh farm goods, artisan products, dinner options, wine, and now beer, alongside free rotating live music curated by Janet Emma Garbe. The market also includes monthly family-friendly programming courtesy of Oak Spring Garden Foundation.
That programming detail matters more than it reads. Buchanan Hall is not a farmers market operator; it is a nonprofit event hall that took on the market during the shutdown years and never let it go. For over 100 years, Buchanan Hall has fulfilled its 501(c)(3) mission to provide a central gathering place for cultural and community events. Its commercial commissary kitchen is home to several local food businesses, including Auntie Rachelle of Auntie Rara's Ice Cream. The hall also provides meeting and event space for the Upperville Colt & Horse Show, Virginia Point-to-Point Foundation, Foxcroft School, Wakefield School, Piedmont Fox Hounds, Land Trust of Virginia, and the Piedmont Symphony Orchestra, among others.
For someone who lives here, that list is the point. When you buy an ice cream at the market from Auntie Rara, you are buying from a business that rents a licensed kitchen from the same building where the Herb Society meets. The market is a face on an institution that has been threading civic life together in the village for a century. A few practical notes for the weeks ahead:
- Bring a lawn chair or picnic blanket; there is no formal seating.
- Beer joined the wine offering this season, so plan the walk home accordingly.
- The music rotates, so the Wednesday you skip is not the Wednesday you catch.
- The season closes in October. There are fewer market Wednesdays left in 2026 than most residents count on.
A Thursday-to-Monday Vineyard
Three miles south of the highway on Crenshaw Road, Slater Run sits on land the same family has farmed since long before Virginia was a wine state. A vineyard and winery in Hunt Country, Slater Run continues a family farming tradition. For 300 years, the Slater family has farmed along Goose Creek in Virginia, mostly growing cereal crops and beef cattle. In 2010, they added grapevines to that farming tradition.
The tasting room is worth understanding on its own terms because it is not built around weekend tourism. Hours run Monday and Thursday from 11 AM to 5 PM, and Friday, Saturday, and Sunday from 11 AM to 6 PM, with Tuesday and Wednesday closed. That two-day midweek closure is what keeps the room from feeling like the Loudoun wineries closer to the Beltway. The winemaker, Katell Griaud, was raised at her family's winery in Monbazillac, France, and received her undergraduate and graduate degrees in winemaking from Bordeaux University. A Thursday afternoon tasting here is closer in feel to a working farm office than a bachelorette destination, and the Cabernet Franc reflects it.
How the Week Actually Reads
Put the three anchors on a calendar and a resident's rhythm begins to make sense. The village is not a place you visit; it is a place whose infrastructure rewards showing up on the right day of the week.
- Thursday: Slater Run reopens after its two-day close. A short flight after work, before the weekend crowd finds Crenshaw Road.
- Wednesday, 4:30 to 7:30: Buchanan Hall market. Dinner and produce in the same trip; the walk from the parking lot to the music is under two minutes.
- Sunday: The all-day roast at Hunter's Head. Arriving at 2 PM is now a defensible choice, not a workaround.
- Monday: Closed at the tavern, but Slater Run is open. This is the quiet slot most residents underuse.
- Tuesday: The village genuinely rests. Both Hunter's Head and Slater Run are closed. If you have been trying to figure out why the parking on Route 50 looks strange midweek, this is why.
What Stays the Same
Turnover at three of the village's most-visited addresses would be a bigger story in a place with less continuity underneath. Upperville has more continuity underneath than almost any place in Northern Virginia. For more than two decades, Hunter's Head Tavern has been a cornerstone of Virginia's Piedmont. The building dates back to a 1750 log cabin. It later expanded into what was known as the Old Carr House, serving as a home, general store, and blacksmith shop before falling into disrepair. It was restored in the late 1990s by former owner Sandy Lerner, co-founder of Cisco Systems.
Buchanan Hall carries a similar weight. Established in 1920, the building was constructed by Brigadier General James A. Buchanan, who sought to build an elegant hall in the village of Upperville for his daughter's wedding. The original wooden floors and acoustics have hosted concerts by Patsy Cline, Duke Ellington, and Chauncey Brown. That the same room now hosts a Wednesday market with local bread and cider is not a downgrade. It is what a healthy civic building looks like across a century.
The thesis holds either way you approach it. Upperville is not preserved in the sense of frozen. It is preserved in the sense of maintained by people who keep taking responsibility for it. The tavern changed hands rather than closing. The market grew rather than ending. The vineyard added a French winemaker rather than expanding into a wedding factory. If you live here, the reason your week works the way it does is that a handful of specific people, in specific buildings, made specific decisions this year to keep it working.
That is worth noticing on a Wednesday evening between the cheese vendor and the second glass of wine.
Let's Connect
Understanding how a village actually operates from the inside is the same skill set that matters when a country property changes hands. If you own land, a farm, or a residence in the Upperville area and are thinking through the long arc of stewardship, Bretton Molenaar at Thomas & Talbot Estate Properties is available for a discreet conversation grounded in local knowledge and ownership experience.
