Hunt Country Stable Tour May 2026: Virginia Horse Country

Virginia's Hunt Country Opens Its Gates for One Day This May

If you've ever driven the rolling pastoral corridors of Route 50 between Middleburg and Upperville and wondered what lies behind those white-fenced estates and centuries-old stone walls, Saturday, May 23, 2026 is your answer. The Hunt Country Stable Tour — organized by Trinity Episcopal Church in Upperville — offers a rare self-driven, behind-the-scenes look at some of Northern Virginia's most celebrated private equestrian facilities, working farms, and historic stables.

This annual tradition draws visitors from across the DC metro area and beyond, combining the quiet grandeur of Virginia horse country with genuine access that money can't ordinarily buy. Think Olympic-caliber training rings, heirloom breed operations, and barns that predate the Civil War — all open for one morning and afternoon each spring.

What to Expect on the Tour

The tour is self-driven, meaning you set the pace, pick your stops, and linger as long as you like at the properties that speak to you. Past tours have included working hunter-jumper stables, steeplechase training facilities, and gentleman farms where thoroughbreds share pasture with heritage cattle. The route winds through Upperville, Middleburg, and The Plains — three of the most visually stunning communities in the Virginia Piedmont.

Whether you're a serious equestrian or simply someone who loves the landscape and history of hunt country, the tour is a genuine insider experience. It's the kind of day that photographs well and stays with you — the smell of fresh hay, the sound of hooves on packed earth, the scale of the Blue Ridge visible in every direction.

Make It a Full Weekend: Pair with Rappahannock Wine Country

The Hunt Country Stable Tour sits at the northern edge of a natural long-weekend itinerary for visitors based in or traveling through the Rappahannock County region. The drive from Upperville to Sperryville or Washington, VA runs about 45 minutes — making it easy to combine the stable tour on Saturday with a full day in Rappahannock on Sunday.

Wine lovers will find the region around Washington, VA dotted with tasting rooms worth building an afternoon around.
Foodies have no shortage of options in Sperryville and the surrounding area, from farm-to-table dining to artisan bakeries.
Lodging options in the region range from historic B&Bs in Washington, VA to vineyard cottages near Old Rag Mountain — book early for May weekends, which fill quickly as the spring season hits full stride.

About the Organizer

The Hunt Country Stable Tour is a long-running fundraiser presented by Trinity Episcopal Church, Upperville — one of the oldest Episcopal parishes in Virginia and itself a landmark worth seeing. Proceeds from the tour support the church's community programs. Tickets and route maps are typically available in advance; check with Trinity Episcopal Church Upperville directly for 2026 pricing and registration details as the date approaches.

Planning Your Visit

Event: Hunt Country Stable Tour
Date: Saturday, May 23, 2026
Tour Area: Upperville, Middleburg, and The Plains, Virginia
Format: Self-driven (your own vehicle)
Organizer: Trinity Episcopal Church Upperville
Tip: Start early — morning light in hunt country is extraordinary, and popular properties can draw small crowds by midday. Wear comfortable shoes; stable yards are not always paved.
Combine with: A Sunday in Rappahannock County — Sperryville, Washington VA, and the surrounding wine trail are roughly 45 minutes south on scenic back roads.

Note: Ticket prices and specific property listings for the 2026 tour had not been publicly announced at time of publication. We recommend contacting Trinity Episcopal Church Upperville directly for the latest details as May approaches.