Most days, Trappe Road just outside the village runs quiet past a locked gate and a stretch of pasture with Blue Ridge views nobody but the farm's own crew gets to walk. Ayrshire Farm has operated that way for years: a working organic operation, not a place you drop by. The one exception is Loudoun County's Fall Farm Tour, and this year the weekend lands on October 17 and 18.
For two days, one of Upperville's oldest working farms becomes the most public building in the village, and the timing does something worth noticing. The same weekend, Hunter's Head Tavern down the road on Route 50 is running its first fall season under new ownership since reopening in March, and the meat on that menu comes from the same pastures the Farm Tour opens up for a look. A resident who spends Saturday morning at the gate and Saturday night at the bar has effectively walked the entire supply chain between two points on the same two-mile stretch of highway.
What the gate actually opens onto
Ayrshire Farm is Virginia's first Certified Humane and Organic farm, and the Fall Farm Tour is the one weekend a year the public gets past the entrance at 21846 Trappe Road. The farm is one stop among 34 across Western Loudoun this year, part of a tradition that started in 1993 as a Fall Colors driving tour before it turned into the harvest-season, working-farm event it is now. Both days run 10 a.m. to 4 p.m., and the visit is built around a hayride from the parking area up to the main house and stables, past orchards and pastures with the mountains in the background.
The animals are the reason people actually come. Ayrshire raises heritage breeds that don't show up on most Loudoun farms: Scottish Highland, Ancient White Park, and English Longhorn cattle, Gloucestershire Old Spot pigs, Broad Breasted Bronze turkeys, and the Shire draft horses that do double duty pulling the hayride and working the soil between seasons. The farm store stays open through the visit, selling eggs, honey, and WholeHarvest Meat Boxes, along with stone-ground flours, grits, and cornmeal from Locke's Mill. This is also the weekend to reserve a Thanksgiving turkey if that's on the list, since the farm doesn't take walk-in orders the rest of the year the way it does during Tour weekend.
Where the loop closes
The building that now houses Hunter's Head Tavern has been on that stretch of Route 50 for nearly three centuries. It started as a log cabin built around 1750 by a Scotsman named Stephen McPherson on land he bought from the Reverend Dr. Charles Green, one of the Piedmont's early settlers. The cabin was expanded in the early 1800s into what locals called the Old Carr House, a building that at various points served as a general store, a blacksmith shop, and a home on what was then a 2,500-acre estate. The village itself takes its name from Joseph Carr, whose family bought the property and gave Upperville its identity.
The tavern opened in 2001 and built its reputation as the only farm-owned gastropub in the Piedmont, running on beef, pork, poultry, and eggs supplied by Ayrshire Farm just down the road. That supply relationship didn't change when the building did. Hunter's Head closed temporarily in December for renovations after a change in ownership, and reopened in March under new owners Noel and Alannah Sweeney, who brought in James Beard-nominated chef and Master Sommelier Jarad Slipp to run the menu. Slipp owns Tremolo and Knead Wine in Middleburg and previously served as estate director at RdV Vineyards, and his arrival marks the tavern's first real menu overhaul in years while keeping the same farm-to-table backbone it opened with.
What that means for anyone spending the weekend in the village is straightforward. The animals you meet at the farm gate on Saturday afternoon are the same breeds supplying the kitchen you'd walk into that night, and this fall is the first time both halves of that loop are running under fresh direction at the same time.
The other invitation on the same Saturday
October 17 isn't only a farm-tour day. Wheatland Equestrian is holding its Annual Gala Dinner that evening at Belle Grey Farm, also in Upperville, which means the village is hosting two very different versions of the same agricultural identity on the same date: a barefoot, kid-friendly morning at Ayrshire and a formal evening fundraiser a few miles away. Neither event competes with the other in any real sense, but they do split the day, and residents planning around both will want to treat Saturday as two separate outings rather than one long one.
The smaller thread worth knowing
Village Cheese Works of Upperville doesn't run a public event this weekend, but it's worth knowing the name. The cheesemaker supplies farm stores and markets around the county, and its presence on shelves alongside beef, honey, and flour from farms like Ayrshire is a reminder that Upperville's food economy isn't only horses and hunt breakfasts. It's a working dairy and meat supply chain that mostly stays invisible until a weekend like this one puts a farm gate wide open.
Planning the actual weekend
A few practical notes for anyone mapping out October 17 and 18:
- Ayrshire Farm is open 10 a.m. to 4 p.m. both days, rain or shine, with no admission charge.
- Thanksgiving turkey reservations are best made in person at the farm store during Tour weekend, since walk-in ordering isn't available the rest of the year.
- Hunter's Head Tavern's hours run Monday, Thursday, Friday, Saturday, and Sunday, with Tuesday and Wednesday closed, so a Saturday dinner reservation is the safer bet than a weekday drop-in.
- Wheatland Equestrian's gala at Belle Grey Farm is a ticketed evening event separate from the Farm Tour, worth checking directly with the organization for availability.
- With 34 farms participating countywide this year, planning even a short Ayrshire-and-tavern day still leaves room to add one or two more stops without overcommitting the weekend.
The two-day window closes fast. By October 19, the gate at Ayrshire goes back to being just a gate, and the loop between farm and tavern goes back to running quietly, the way it does the other 363 days of the year.
If you're weighing whether Upperville's mix of working farms, historic taverns, and quiet back roads is the kind of place you want to call home, Beckwith Bolle knows this village at ground level and can talk through what living here actually looks like beyond one good weekend.
