Overview
Henley's Orchard sits at 2192 Holly Hill Farm in Crozet, in the foothills of the Blue Ridge a few miles west of The Square. The orchard has been continuously farmed by the Henley family since 1932, through four generations and most of the twentieth century's worth of agricultural change in central Virginia. It is now an estate cidery, a wholesale and retail orchard, a wedding venue, an event barn, and the host of one of the village's best fall traditions.
Almost no business in the Charlottesville area has the family-continuity story Henley's has. That is the thing to know going in.
Family-run since 1932
The orchard was established in 1932 by Joseph T. Henley, Sr. Joe held a degree in agriculture and was the first State Fruit Inspector for the Commonwealth of Virginia, which gave him the technical fluency to turn a small homestead into a working farm. He bought the original 5 acres for an apple orchard. Over the next 28 years, he expanded the apple operation, planted peaches, started a herd of cattle, and put many acres into hay. By the time Joe handed off the farm, it was a serious agricultural concern.
The orchard passed to Joe's son, Joseph T. Henley, Jr., who expanded it further. From Junior, it passed to his son Tim Henley. Today, Tim and his wife Sarah run Henley's together with their three adult children:
- Jacquelyn Henley, Head Cider and Wine Maker at the Estate Cidery. Also runs Central VA Horse Boarding and teaches horseback riding when she isn't pressing fruit.
- Brook Henley, Chief Financial Officer of the Henley Organization. Manages operations across the orchard, cidery, and wedding venue. Generally accompanied by his dog, Kevin.
- Steele Henley, Chief Mechanical Officer. The person you'll find on, under, or repairing one of the tractors, trucks, and miscellaneous farm machinery that an operation this size requires.
The Henleys also expanded the wholesale market into Richmond and Harrisonburg and upgraded the retail operation, which they call The Shed. The Shed is what most visitors interact with, a tasting room, retail counter, and gathering space.
What's grown, what's poured
The orchard runs apples and peaches as its core crops. Apples are the foundation; peaches are seasonal but substantial. Pumpkins and a handful of other fall produce round out the late-season offering. Most of the wholesale fruit goes to grocery and farm-market accounts in central Virginia.
The Estate Cidery, Jacquelyn's domain, produces hard ciders and peach wine from the orchard's own fruit. The lineup rotates with what's pressed, but the staples are dry to off-dry hard ciders, a peach wine made from estate peaches, and seasonal small-batch experiments. The tasting flight at The Shed walks you through whatever's pouring on a given visit.
You can pick up cider by the bottle to take home, glasses to drink on the property, and gift packs through the holiday season. The cidery is dog-friendly and family-friendly outdoors. Indoors, the tasting bar is more grown-up but still casual.
HenleyFest and the calendar
The headline event is HenleyFest, every weekend in October. Live music, hayrides, a pumpkin patch, food trucks, a bonfire on cooler nights, the farm-festival atmosphere that draws Charlottesville families out for an afternoon. Each weekend has its own programming; the cidery and orchard run extended hours through the month. Tickets and weekend-specific details on henleysorchard.com.
Outside of October, the orchard hosts weddings at the property's event barn and ceremony lawn, Sarah and Brook handle the venue side. Capacity ranges depending on configuration; the venue books well in advance. Couples looking at Henley's almost always also walk King Family Vineyards, Stinson, and Veritas; each property handles a different style of event.
Visiting
Address: 2192 Holly Hill Farm, Crozet, VA 22932. Phone (434) 823-7848.
Tasting room hours: Thursday through Sunday during the regular season; expanded hours during HenleyFest and the holiday months. Confirm before driving out, the orchard's website calendar is the source of truth.
Pick-your-own: the orchard runs limited PYO depending on crop conditions. Apples are usually the main PYO offering in late September and October, peaches in midsummer when the crop is on. Check ahead.
The Shed: retail counter for cider, peach wine, gifts, and seasonal produce. Open most of the year; expanded in fall.
The drive out is part of the experience. Holly Hill Farm Road winds through farm country with the Blue Ridge to the west. On a clear October weekend, the trip is one of the genuinely scenic drives in the Crozet area.
Why it matters
Most American small farms that started in 1932 are gone. The ones that survived made it through the consolidation of the 1960s and 70s, the corporate-agriculture wave of the 80s, the suburbanization pressure of the 90s and 2000s, and the wedding-and-cidery pivot that has kept a handful of orchards in this part of Virginia commercially viable through the 2010s and 2020s. Henley's made it through all of those by adapting at each stage, wholesale apples, then peaches, then cattle, then weddings, then cider, then HenleyFest, without selling and without breaking up the land.
Four generations is a long time. The Henley kids running the orchard now grew up on it, and so did their father, and so did their grandfather, and the great-grandfather who started it knew agriculture well enough to be the state's first fruit inspector. That kind of continuity is hard to fake and hard to overstate the value of in a small community.
If you have an hour and want to spend it in Crozet on a fall Saturday, drive out. Get a flight at the cidery. Walk the orchard. Buy a peach or two for the road. The trip is the point.
More cidery in Crozet
Frequently asked questions
Where is Henley's Orchard Estate Cidery?
Henley's Orchard Estate Cidery is located at 2192 Holly Hill Farm, Crozet, VA 22932, in Crozet, Virginia.
How do I contact Henley's Orchard Estate Cidery?
You can call (434) 823-7848 or visit https://www.henleysorchard.com. Hours and current information are most reliable directly from the business.
What kind of business is Henley's Orchard Estate Cidery?
Henley's Orchard Estate Cidery is categorized as cidery in our Crozet directory. See the description and quick facts above for what makes this listing distinctive.
