Virginia Piedmont · A concierge named Charles

Tell us when you're coming. We'll shape the trip.

Charles knows the gravel roads — the wineries worth the drive, the table that's hard to get — and quietly handles the bookings for you.

Meet Charles — your Piedmont concierge. He keeps the book on this country: the roads, the tables worth pulling strings for, the by-arrangement moments you won't find online. Tell him what you're after and he'll draft the days free.

Shape my wine-country weekend We're staying at a luxe inn Do Skyline Drive & Old Rag right Arrange something private

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Rappahannock County Farm Tour

Explore the Farms of Beautiful Rappahannock County

Waterford Fair

An 82-year tradition of heritage crafts, historic homes tours, and Americana in a National Historic Landmark village

Old Town Warrenton Fall Festival

A day of art, music, food, and strolling entertainment on Main Street in historic Old Town Warrenton

Virginia Fall Races

Steeplechase racing at Glenwood Park, Virginia's oldest continuous racecourse, just outside Middleburg

Middleburg Film Festival

Four days of awards-season cinema, panels, and galas in Virginia's hunt-country town of Middleburg

International Gold Cup

The fall steeplechase classic at Great Meadow, run over the timber and hurdle courses in late October

RAAC Fall Art Tour

Artists of Rappahannock

Montpelier Hunt Races

Steeplechase racing on the grounds of James Madison's Montpelier, the first Saturday in November

Virginia Gold Cup

Virginia's biggest day of steeplechase racing, run at Great Meadow on Kentucky Derby Saturday

Coming Up

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Copper Fox Distillery

Artisan distillery producing Wasmund's single malt whiskey with daily tours.

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Chester Gap Cellars

Boutique estate winery at 1,000-1,300 feet elevation on the Shenandoah Mountains.

DuCard Vineyards

Award-winning vineyard bordering Shenandoah National Park.

Foster Harris House

Luxury historic B&B with five elegant rooms and gourmet breakfast.

Gadino Cellars

Family-owned vineyard and winery near Shenandoah National Park.

Gay Street Gallery

Fine art gallery presenting award-winning representational landscape and figurative paintings.

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Gay Street Inn

Restored 1850s farmhouse B&B with five rooms and mountain views.

Glen Manor Vineyards

Award-winning winery with distinctive terroir in the Rappahannock region.

Middleton Inn

AAA Four Diamond historic inn circa 1840 with mountain views and stables.

Sharp Rock Vineyards Cottages

Two private cottages on vineyard with river views and Old Rag Mountain access.