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September 13, 2025
Charlottesville, VA

Hayley & Oliver

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    Things To Do

Things To Do

Downtown Mall

Charlottesville, VA 22902

Enjoy local dining, boutiques, galleries, and historic architecture on one of the longest pedestrian malls in the U.S.!

Monticello Wine Trail

Charlottesville, VA 22902

Enjoy tastings at some of our favorite vineyards like King Family Vineyards, Barboursville Vineyards, Pippin Hill Farm & Vineyards, and countless others - all offering scenic views and delicious wines!

Charlottesville City Market

100 East Water Street, Charlottesville, VA 22902

Enjoy the Saturday morning farmer's market, located near the downtown mall, with fresh produce, artisanal goods, and local crafts.

Eat & Drink

Feel free to ask us about specific recommendations but a few of our local favs are Bodo's Bagels, Ivy Provisions, Take It Away, Tavola, Lampo Pizza, Continental Divide, The Alley Light, and SO many more!

Outdoor Adventures

Take a hike the in Blue Ridge Mountains/Shenandoah National Park on Skyline Drive, just 30 minutes away. You can also visit the Saunders-Monticello Trail –an accessible walking path that leads toward Thomas Jefferson’s Monticello.

Carter Mountain Orchard and Country Store

1435 Carters Mountain Trail, Charlottesville, VA 22902

A local orchard with apple picking, cider slushies & donuts (the BEST), and hayrides - great for guests of all ages!

Historical Sightseeing

Tour Monticello (Thomas Jefferson’s historic home and gardens), Highland (the lesser-known estate of James Monroe for a quieter historic experience), or the Rotunda & UVA Lawn (University of Virginia’s central campus).

For all the days along the way
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