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Day 6Mon, Aug 31, 2026

Charlottesville Loop

Peach orchard, UVA (Poe Room), wineries, Monticello and Highland — back to the Iris Inn.

17

Stops

3h 41m

Drive

113

Miles

$21

Fuel

Tourist Info (PDF)

Original itinerary PDF

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The Route

Stop by Stop

  1. 1

    Iris Inn

    191 Chinquapin Dr, Waynesboro, VA

    📞 (540) 943-1991🔗 Website

    Garden Path Cottage • Breakfast 8–10

    Documents (0)

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    12 miles
  2. 2

    Chiles Peach Orchard

    1351 Greenwood Rd, Crozet, VA

    📞 (434) 823-1583🔗 Website

    Hours: 9–6

    Documents (0)

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    12 miles
  3. 3

    Charlottesville Safety Rest Area

    I-64 W, mile 113, Charlottesville, VA

    Documents (0)

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    19 miles
  4. 4

    Foods of All Nations

    2121 Ivy Rd, Charlottesville, VA

    📞 (434) 296-6131🔗 Website

    International grocery • 7:30 – 7

    Documents (0)

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    0 miles
  5. 5

    The Aviator Statue

    160 McCormick Rd, Charlottesville, VA

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    0 miles
  6. 6

    Edgar Allan Poe Room

    13 West Range, Charlottesville, VA

    UVA — museum display

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    3 miles
  7. 7

    Costco

    3171 District Ave, Charlottesville, VA

    📞 (434) 328-7023🔗 Website

    Gas up for next day

    Documents (0)

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    12 miles
  8. 8

    Eastwood Farm and Winery

    2531 Scottsville Rd, Charlottesville, VA

    📞 (434) 264-6727🔗 Website

    12–5 • 5 pours • Cheese $28, Chocolate $12

    Documents (0)

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    8 miles
  9. 9

    Trump Cidery

    3550 Blenheim Rd, Charlottesville, VA

    📞 (434) 326-5032🔗 Website

    Flight of 3/6 flavors • 12–6

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    0 miles
  10. 10

    Trump Winery

    3550 Blenheim Rd, Charlottesville, VA

    📞 (434) 984-4855🔗 Website

    11–5 • Tastings $25–$45

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    4 miles
  11. 11

    James Monroe's Highland

    2050 James Monroe Pkwy, Charlottesville, VA

    📞 (434) 293-8000🔗 Website

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    0 miles
  12. 12

    Jefferson Vineyards

    1353 Thomas Jefferson Pkwy, Charlottesville, VA

    📞 (434) 977-3042🔗 Website

    11–6 • 8-pour w/ pairing $50

    Documents (0)

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    2 miles
  13. 13

    Michie Tavern

    683 Thomas Jefferson Pkwy, Charlottesville, VA

    📞 (434) 977-1234🔗 Website

    Mid-Day Faire 11:30–3 • $26.95

    Documents (0)

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    1 mile
  14. 14

    Carter Mountain Orchard

    1435 Carters Mountain Trl, Charlottesville, VA

    📞 (434) 977-1833🔗 Website

    9–6 • Wine flights

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    3 miles
  15. 15

    Thomas Jefferson's Monticello

    1050 Monticello Lp, Charlottesville, VA

    📞 (434) 984-9800🔗 Website

    Walking involved

    Documents (0)

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    25 miles
  16. 16

    Rockfish Gap Visitors Center

    20 Afton Circle, Afton, VA

    📞 (540) 943-5187🔗 Website

    Gas stop

    Documents (0)

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    4 miles
  17. 17

    Iris Inn

    191 Chinquapin Dr, Waynesboro, VA

    📞 (540) 943-1991🔗 Website

    Documents (0)

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