Horse Country & Wine: A May Weekend in Virginia's Hunt Country

Two Days, One Great Loop: Hunt Country Meets the Blue Ridge

If you're a DC-area traveler who loves wide-open landscapes, locally raised food, and the kind of quiet that's genuinely hard to find, the last weekend of May 2026 offers a rare convergence. On Saturday, May 23, the annual Hunt Country Stable Tour opens the gates of some of Virginia's most storied private equestrian estates in Upperville, Middleburg, and The Plains. Extend the trip by an hour west, and you land in Rappahannock County — where the Sperryville River District, working farms, and craft producers make for a complete weekend with almost no overlap.

Saturday: The Hunt Country Stable Tour

Organized by Trinity Episcopal Church Upperville, this self-driven tour takes visitors behind the gates of private equestrian facilities that are rarely open to the public. Think manicured hunt fields, historic barns, championship-level show facilities, and the kind of Virginia horse culture that's been quietly thriving since the 18th century.

The tour is self-paced, so you control how long you linger at each stop. Upperville itself sits on Route 50 about 55 miles from Washington, DC — and it's a natural corridor heading west toward Rappahannock County on Route 211. If you're already out there on a Saturday, continuing to Sperryville or Washington, VA adds roughly 40 minutes to the drive and drops you into an entirely different kind of Virginia countryside.

Saturday Evening: Sperryville River District

By late afternoon, the Sperryville River District is worth a stop. This cluster of studios, shops, and eateries along the Thornton River sits at the foot of Old Rag Mountain and has a distinctly unhurried character that pairs well with a long weekend mindset.

The district is home to several creative venues — including River District Arts at 7 River Lane, housed in a restored 1930s apple packing facility — as well as Copper Fox Distillery at 9 River Lane, where Wasmund's single malt whiskey is produced with daily tours. Note that Copper Fox's current operating status hasn't been confirmed recently, so it's worth calling ahead at (757) 903-2076 before making it a firm stop.

For dinner, New Iberia Kitchen at 3 River Lane offers Spanish and Louisiana-inspired comfort food in a converted 1930s apple packing shed. The restaurant recently announced its Sunday brunch resuming on April 20 at 10 AM, suggesting the kitchen is active — though a quick call to (540) 227-6647 or a check of their website at newiberiakitchen.com is advisable before you plan your evening around it.

Sunday: Farm Country and Free Concerts on the Horizon

Rappahannock County's Sunday morning moves at its own pace. If you're staying over, the area around Flint Hill and Washington, VA rewards slow driving and unhurried mornings.

Bean Hollow Grassfed at 15A Over Jordan Farm Lane in Flint Hill is a certified grassfed beef, lamb, and goat operation using regenerative grazing practices — the kind of farm that supplies the restaurants you've been eating at all weekend. Social activity has been quiet recently, so call ahead at (540) 675-1025 or visit beanhollowgrassfed.com before expecting a farm-stand experience.

If you're timing a return trip around the River District's free summer concert series, mark your calendar: the Sperryville Summer Concert Series runs every third Thursday from May through September. The 6th season kicked off May 21 with Rebecca Porter Music (honky-tonk, Appalachian grit, and Chamoru heritage), and future concerts follow the same format — gates at 5 PM, music from 6–8 PM, food trucks on site. All concerts are free, funded in part by a PATH Foundation Better Together grant. Full lineup at raac.org/concerts.

A Note on Venue Verification

Rappahannock County has a remarkably high density of independent venues — wineries, pottery studios, galleries, farm stands, distilleries — but a number of them have gone quiet on social media over the past year or more. Before building an itinerary around any specific stop, a quick phone call is genuinely useful. The venues listed in this article with confirmed intel are the safest bets; others in the area appear to still be operating but haven't been recently active online.

Planning Your Visit

Hunt Country Stable Tour

Date: Saturday, May 23, 2026
Location: Upperville, Middleburg, and The Plains, Virginia
Format: Self-driven tour of private equestrian facilities
Organizer: Trinity Episcopal Church Upperville

New Iberia Kitchen

Address: 3 River Ln, Sperryville, VA 22740
Phone: (540) 227-6647
Website: newiberiakitchen.com
Note: Sunday brunch recently resumed at 10 AM — call ahead to confirm current hours

River District Arts

Address: 7 River Lane, Sperryville, VA 22740
Summer Concerts: Every third Thursday, May–September; Gates 5 PM, Music 6–8 PM; Free admission
More info: raac.org/concerts

Copper Fox Distillery

Address: 9 River Lane, Sperryville, VA 22740
Phone: (757) 903-2076
Website: copperfoxdistillery.com
Note: Call ahead to confirm current tour hours

Bean Hollow Grassfed

Address: 15A Over Jordan Farm Lane, Flint Hill, VA 22627
Phone: (540) 675-1025
Website: beanhollowgrassfed.com
Note: Verify farm-stand availability before visiting