Horse show week hides how small Upperville actually is. For seven days at the start of June, Grafton Farm and the Salem Showgrounds fill with international riders, seventy-plus boutique vendors, and the two new 2026 additions to the schedule: a $25,000 Thoroughbred Hunter Derby and an $8,000 Thoroughbred Jumper Classic. Then the trailers pull out, Route 50 goes quiet again, and the village returns to what it is the rest of the year — a mile of stone walls, one church steeple, one working tavern, and a lot of gated driveways.
That thin roster is the thing to understand about summer here. TripAdvisor lists two restaurants inside Upperville proper. The main winery is closed most of the week. The most famous garden opens to the public only a handful of times a year. Once you know which anchors are open on which days, the summer plans themselves. If you don't, you drive Route 50 and wonder where everyone went.
The First Weekend Is Slater Run's Weekend
Slater Run Vineyards, at 1500 Crenshaw Road, is the anchor most residents plan around, and the reason is a scheduling quirk that isn't obvious from the road. Slater Run is normally closed to the public. From May through October, it opens the tasting patio only on the first weekend of the month for wine and views out over hunt country. That's it. Miss the first weekend, and you're waiting until the next one.
The Patusky and Slater families have been farming the Goose Creek property for 300 years, added grapes in 2010, and now run a fully solar-powered winery producing 19 wines from 13 acres of vines. The dry French style and the by-appointment cadence are deliberate. If you live within thirty minutes of Upperville, the useful thing is to put the first Saturday of every summer month on the calendar in January and treat everything else as a bonus.
Hunter's Head Has a Different Kitchen Now
The other permanent anchor is Hunter's Head Tavern, at 9048 John S. Mosby Highway, in the Old Carr House. The building dates to the mid-1700s. Sandy Lerner bought it in 2001, restored the exposed beams and fireplaces, and built the menu around meat, poultry, and eggs from her own Certified Humane and Organic operation up the road at Ayrshire Farm. That supply chain still runs, which is why Hunter's Head is described as the Piedmont's only farm-owned gastropub.
What has changed is the kitchen. Hunter's Head is now operating under Jarad Slipp, who came up through the wine program at RdV Vineyards before that estate was sold to the Bouygues family of Bordeaux and renamed Lost Mountain Vineyards. Reviews since the transition are mixed. Some longtime regulars say the menu has narrowed, and the execution isn't yet as good as it was in the Lerner years. Others visiting in June 2026 report that the patio experience is the same one they remember, dogs are welcome, and the Sunday roast is intact. For a resident, the practical read is that the room and the sourcing are still the reasons to go, and the menu is in a period of resettlement, worth checking a second time if a first visit under the new team disappointed.
Note the hours before you drive. The tavern is closed on Tuesday and Wednesday and opens at 11 the rest of the week. That two-day gap in the middle of the week is the single most common reason people show up to a locked door.
What the Horse Show Actually Adds to the Summer
The Upperville Colt & Horse Show ran June 1 through 7 this year and remains, at 173 years old, the oldest horse show in the United States. It has been held on the same Grafton Farm and Salem Showgrounds along Route 50 since 1853. Admission and parking are free all week, which is the part that matters if you live nearby.
The 2026 program leaned harder on public-facing programming than in past years. Beyond the two new Thoroughbred classes, the week included the Wall of Honor ceremony, a Therapeutic Equine Celebration, a Pup Parade on Saturday, Leadline classes for the youngest riders, and the Horses & Horsepower Invitational Car Show on Sunday. Art Under the Oaks ran Wednesday through Saturday. More than seventy retail vendors and food trucks worked the grounds. For residents, the horse show is less an event to attend once than a week where the village functions like a small festival grounds you can drop into for an hour between errands.
The Walk Between the Villages
The most underused piece of Upperville's summer is the Goose Creek Bridge, roughly halfway between Upperville and Middleburg off Route 50. It's a preserved Civil War site marking an 1863 cavalry and artillery engagement, with a small parking area, one modest sign at the highway, an interpretive path, and a short walk across the stone bridge itself. The entire loop is less than a half mile and takes less than an hour.
The reason to know about it is what it does to a summer afternoon. A first-weekend Slater Run visit ends around five. Hunter's Head opens for dinner. Goose Creek Bridge fills the gap without a drive back into Middleburg, and the shaded stone-and-water setting is one of the few free, publicly accessible outdoor spots in this stretch of Route 50 that isn't private land behind a hedge.
Oak Spring and Trinity, Working in the Background
Two Upperville landmarks shape the village's summer even when they aren't open. Trinity Episcopal Church sits on a thirty-five-acre campus with a French Norman steeple visible from most of Route 50 in town. The parish dates to the 1800s; the current building was rebuilt in the 1950s as a gift from Paul and Bunny Mellon. The church also runs Trinity Thrift and Boutique, which is the closest thing Upperville has to a shopping stop and is worth checking on a slow Saturday for the kind of estate consignment that tends to filter through a village of this size.
Oak Spring, the Mellon family's four-thousand-acre estate at the edge of the village, is the other quiet anchor. Bunny Mellon, who helped Jackie Kennedy design the White House Rose Garden, kept a walled garden here called Little Oak Spring — reflecting pools, mature trees, a cottage full of baskets. The Oak Spring Garden Foundation opens the property to the public only a few times each year, and the summer openings fill up quickly. Watching the foundation's public program calendar is the single thing that separates residents who have been inside Oak Spring from those who have driven past it for a decade.
A Saturday That Actually Sequences
Once you understand which anchors are open on which days, a summer Saturday in Upperville stops requiring guesswork. A version that works on the first weekend of the month, in July or August:
- Late morning at Slater Run's patio while the temperature is still manageable, first-weekend hours only
- A stop at Trinity Thrift and Boutique on the way back through the historic district
- Mid-afternoon walk across Goose Creek Bridge, shaded and short
- Dinner at Hunter's Head Tavern, Thursday through Sunday hours, patio if the dog is coming
On the other three weekends of the month, the sequence collapses to Hunter's Head and the bridge, or a longer drive out to Bluewater Kitchen, and most residents use those weekends for their own gardens, the horse show grounds when there's a fall event, or the drive to the wineries clustered around Delaplane and Markham, eight miles west. The point is that Upperville isn't slow in summer. It's scheduled. The village rewards residents who read the calendar, while confusing everyone else.
If you're thinking about what a summer here actually looks like from inside a house on one of these lanes, or you already own here and are wondering what the market is doing on the properties you drive past every day, that's the conversation I like having in person. Diana Geremia has represented buyers and sellers across Western Loudoun and the Piedmont for nearly two decades and knows the difference between the Upperville the road signs show and the Upperville that runs on first-weekend patios and Thursday-through-Sunday kitchens. Let's Connect.
