Things To Do
🍷 Things to Do in Charlottesville, VA
🌿 Explore Downtown Charlottesville:
Sunset drinks at The Doyle Hotel rooftop bar
Brunch at Bluegrass Grill & Bakery
Gourmet bites at Feast Market
Live music at Miller’s
🏛️ History & Iconic Landmarks:
UVA Lawn & Rotunda - (UNESCO World Heritage Site)
Monticello – Thomas Jefferson’s historic home and gardens
Montpelier – Home of James Madison
Highland – Estate of President James Monroe
🍇 Wineries & Breweries: Monticello Wine Trail
Pippin Hill Farm & Vineyards – Stunning views + elevated dining
King Family Vineyards – Beautiful setting + polo on Sundays
Veritas Vineyard & Winery – Classic Virginia wine experience
Barboursville Vineyards – Historic ruins + refined tastings
🌄 Outdoor Adventures:
Shenandoah National Park – Incredible, early fall colors
Blue Ridge Mountains – Rolling hills + vineyards
Appalachian Trail – Day hikes
💆 Relax & Unwind
Golf & spa day at Keswick Hall
The Clifton Inn – Elegant, countryside dining experience
Keswick Hall Resort & Golf Course
701 Club Drive, Keswick, VA 22947, (434) 979-3440
Monticello
1050 Monticello Loop, Charlottesville, VA 22902, (434) 984-9800
The Doyle Hotel Rooftop Bar - UP On The Roof
499 West Main Street, Charlottesville, VA 22903, (434) 205-0056
For all the days along the way