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Virginia Wine Country Road Trip

Progressive farms and serious wineries have blossomed in recent years, but life here continues at a blissfully slow pace
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Rating: 5 out of 5 by EveryTrail members
Difficulty: Easy
Duration: Multiple days

Overview :  East of the Blue Ridge Mountains, the Piedmont region of Virginia still has the same rolling hills and fields that captivated Thomas... more »

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Points of Interest

The restored interior of this intimate inn’s Georgian villa, in Virginia’s burgeoning wine region 20 miles from Charlottesville, is a refined mix of damask, oil paintings, four-poster beds, and claw-foot tubs. Three palatial suites have private balconies with views of the vineyards, lake, and majestic Blue Ridge Mountains; the Octagon Suite also... More

2. Bittersweet

The Warehouse District shop sells flirty silk tops and Frye boots.

Address:
106 E. Main St.
Charlottesville, Virginia
United States

Phone:
(434) 977-5977

3. Calhoun’s Country Hams Shop

For more than 40 years, folks have flocked here for hand-rubbed, air-cured meats. Sandwiches are piled high with silky slices; pick up a bone-in whole ham to bring home.

Address:
219 S. East St.
Culpeper, Virginia
United States

Phone:
(540) 825-8319

Built by a master carpenter on the edge of the University of Virginia campus in 1817, the eight-room hotel retains its Federal-era charm with carved fireplace mantels and four-poster beds.

Address:
1211 W. Main St.
Charlottesville, Virginia
United States

Phone:
(434) 974-4663

5. Georgie

The shop stocks dresses by Alice + Olivia and 3.1 Phillip Lim.

Address:
126 Garrett St.
Charlottesville, Virginia
United States

Phone:
(434) 295-5001

6. Main Street Market

A hive of shops perfect for supplying a picnic basket.

Address:
416 W. Main St.
Charlottesville, Virginia
United States

In 1770, Jefferson sold some of the land surrounding Monticello, his sprawling Palladian home up in the hills just outside Charlottesville, to an Italian grower whose experiments with hybrid American-European grapes were among the first such plantings this side of the Atlantic. Grape growing at Monticello ceased by the 19th century, but the old... More

The juicy pulled-pork platter draws ‘cue fans from across the state. Sides of sugary baked beans and heaps of crispy fries don’t hurt either.

Address:
313 Washington St.
Madison, Virginia
United States

Phone:
(540) 948-3130

9. Pillow Mint

The shop sells John Robshaw quilts and Blissliving bedsheets.

Address:
310 Second St. S.E.
Charlottesville, Virginia
United States

Phone:
(434) 293-3582

Dishes at wood-beam-ceilinged The Local showcase homegrown ingredients, as in Blue Ridge Mountain brook trout with Cajun rémoulade. Virginia gets its own section on the wine list.

Address:
824 Hinton Ave.
Charlottesville, Virginia
United States

Phone:
(434) 984-9749

Tour this Jefferson-built institution.

Address:
Charlottesville, Virginia
United States

Phone:
(434) 924-7969

12. White Hall Vineyards

The winery makes a jammy Petit Verdot.

Address:
5282 Sugar Ridge Rd.
White Hall, Virginia
United States

Phone:
(434) 823-8615