Hunt Country & Wine: A Rappahannock Spring Weekend

A Blue Ridge Spring Weekend Worth Planning Around

If you're mapping out a late-May escape from the DC metro area, the stretch of Virginia between Middleburg and the Blue Ridge foothills is about as good as it gets right now. The landscape is fully green, the mountain views are clear, and the region's farms, wineries, and artisan makers are hitting their spring stride. This guide shows you how to string together a genuinely memorable two-day trip — anchored by the Hunt Country Stable Tour on Saturday, May 23 — with stops in and around Rappahannock County on either side.

Saturday: Hunt Country Stable Tour (May 23, 2026)

The centerpiece of this weekend is the Hunt Country Stable Tour, organized annually by Trinity Episcopal Church in Upperville. This self-driven event takes visitors behind the gates of some of Virginia's most storied private equestrian facilities — working stables, meticulously kept farms, and estates that are otherwise closed to the public. Stops span Upperville, Middleburg, and The Plains, giving you a rare look at the living tradition of Virginia horse country.

The tour is self-paced by car, which means you can linger at the properties that interest you most and move on when you're ready. If you've ever driven Route 50 west through Middleburg and wondered what's behind those stone walls and white board fences, this is your answer. Check directly with Trinity Episcopal Church Upperville for ticket details, route maps, and any morning start times before you go.

What to Expect on the Tour

Behind-the-scenes access to private equestrian facilities not otherwise open to visitors
Working farms and stables across Loudoun and Fauquier horse country
A self-driven format — go at your own pace, linger where you like
Organizer: Trinity Episcopal Church, Upperville, VA

Plan to spend a solid morning and midday on the tour route, then point your car west toward Rappahannock County for the afternoon and evening.

Saturday Afternoon: Into Rappahannock Wine Country

From The Plains or Upperville, it's roughly 30–40 minutes west on Route 211 or 522 into the heart of Rappahannock County — and the transition from manicured hunt country to Blue Ridge farmland is itself part of the experience. The road narrows, the mountains get bigger, and the pace slows down in the best possible way.

The county has a cluster of wineries that have been drawing weekend visitors for years. Sharp Rock Vineyards sits at the foot of Old Rag Mountain on Sharp Rock Road in Sperryville — an award-winning family vineyard with a setting that's hard to beat on a clear spring afternoon. DuCard Vineyards in Etlan borders Shenandoah National Park directly, making it one of the more dramatically situated tasting rooms in the region. Both are worth a call ahead before visiting, as hours can vary by season.

If you're approaching from the north on Route 211, Magnolia Vineyards in Amissville sits right on that corridor — a cozy farm-style tasting room that makes a natural first stop as you enter the county's orbit.

Saturday Evening: Washington, VA

Spend Saturday night in Washington, Virginia — the county seat and one of the most charming small towns in the mid-Atlantic. The historic district along Gay Street and Main Street is walkable and unhurried. Several lodging options have long anchored the town, including the Foster Harris House at 189 Main Street (a luxury historic B&B with five rooms and a gourmet breakfast) and the Gay Street Inn at 160 Gay Street (a restored 1850s farmhouse with mountain views). Both are worth reaching out to directly for availability — call ahead, as these are small properties.

While you're in town, Middle Street Gallery on Gay Street and Gay Street Gallery at 337 Gay Street represent over four decades of local fine art history between them — ideal for a pre-dinner browse.

Sunday: Sperryville's River District

Sunday morning belongs to Sperryville. The town's compact River District packs an impressive amount of character into a small footprint — pottery studios, art galleries, a craft distillery, and a small-batch brewery all within easy walking distance of each other.

Copper Fox Distillery at 9 River Lane produces Wasmund's single malt whiskey and reportedly offers daily tours — it's one of the more distinctive stops in the county for spirits lovers. Hopkins Ordinary Ale Works at 47 Main Street operates a small-batch brewery in a B&B cellar setting with a beer garden and unfiltered house beers.

For ceramics, Sperryville Pottery at 42 Main Street offers handcrafted pieces and pottery classes, while River District Potters at 7 River Lane is a four-potter collaborative working in functional and artistic ceramics. River District Arts, also at 7 River Lane, operates out of a restored 1930s apple packing facility — the building itself is worth a look.

Note: Several of these venues have shown limited recent social activity. We strongly recommend calling ahead before building your itinerary around any single stop.

Planning Your Visit

Hunt Country Stable Tour

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

Sharp Rock Vineyards

Address: 5 Sharp Rock Rd, Sperryville, VA 22740
Phone: (540) 987-8020
Website: sharprockvineyards.com
Call ahead to confirm hours before visiting

DuCard Vineyards

Address: 40 Gibson Hollow Ln, Etlan, VA 22719
Phone: (540) 923-4206
Website: ducardvineyards.com

Magnolia Vineyards

Address: 200 Viewtown Rd, Amissville, VA 20106
Phone: (703) 785-8190
Website: magnoliavineyards.com

Foster Harris House (Lodging)

Address: 189 Main Street, Washington, VA 22747
Website: fosterharris.com

Gay Street Inn (Lodging)

Address: 160 Gay Street, Washington, VA 22747
Phone: (540) 316-9220
Website: gaystreetinn.com

Copper Fox Distillery

Address: 9 River Lane, Sperryville, VA 22740
Phone: (757) 903-2076
Website: copperfoxdistillery.com

Hopkins Ordinary Ale Works

Address: 47 Main Street, Sperryville, VA 22740
Phone: (540) 987-3383
Website: hopkinsordinary.com

Sperryville Pottery

Address: 42 Main Street, Sperryville, VA 22740
Phone: (540) 987-1000
Website: sperryvillepottery.com

Many venues in Rappahannock County keep informal hours or adjust seasonally. Always call ahead or check venue websites before making a long drive — it saves disappointment and ensures a better experience.