8 days in Chesterfield & Charlottesville Itinerary

Chesterfield Court House is an unincorporated community that is the county seat of Chesterfield County, Virginia, United States. Keep things going the next day: do a tasting at Upper Shirley and then admire the majestic nature at Pocahontas State Park.

Discover how to plan a Chesterfield trip in just a few steps with Klarna Trips's itinerary builder.

Albany to Chesterfield is an approximately 7.5-hour car ride. Traveling from Albany in September, you can expect nighttime temperatures to be somewhat warmer in Chesterfield, with lows of 63°F. Finish up your sightseeing early on the 10th (Mon) so you can go by car to Charlottesville.

Situated at the foothills of the Blue Ridge Mountains, Charlottesville is perhaps best known as the home of three of the United States' founding fathers, including Thomas Jefferson.

Do some cultural sightseeing at Monticello and James Monroe's Highland. Visit James Madison's Montpelier and Jefferson Vineyards for their historical value. Get out of town with these interesting Charlottesville side-trips: National Museum of the Marine Corps (in Triangle), Virginia Safari Park (in Natural Bridge) and Stonewall Jackson Memorial Cemetery (in Lexington). There's much more to do: do a tasting at Barboursville Vineyards and Historic Ruins, don't miss a visit to University of Virginia, experience rural life at Carter Mountain Orchard, and indulge your taste buds at Pippin Hill Farm & Vineyards.

To see reviews, other places to visit, where to stay, and other tourist information, read our Charlottesville trip maker.

You can drive from Chesterfield to Charlottesville in 1.5 hours. In September, plan for daily highs up to 80°F, and evening lows to 60°F. Finish your sightseeing early on the 15th (Sat) so you can travel back home.