Wolftrap Farm has a long list of recommendations on their website for things to do nearby. Some of the highlights are listed here, but the full site is thewolftrapfarm.com/guest-information-booklet.
Monticello
931 Thomas Jefferson Pkwy, Charlottesville, VA 22902, (434) 984-9800
James Madison's Montpelier
11350 Constitution Highway, Montpelier Station, VA 22957, (540) 672-2728
Wilderness Battlefield
35347 Constitution Highway, Orange, VA 22160, (540) 693-3200
The Exchange Hotel Civil War Medical Museum
400 North Main Street, Gordonsville, VA 22942, (540) 832-2944
James Madison Museum of Orange County Heritage
129 Caroline Street, Orange, VA 22960, (540) 672-1776
Barboursville Vineyards
17655 Winery Road, Barboursville, VA 22923, (540) 832-3824
This is Emily's favorite winery of all time.
Horton Vineyards
6399 Spotswood Trail, Gordonsville, VA 22942, (540) 832-7440
Honah Lee Vineyard
13443 Honah Lee Farm Drive, Gordonsville, VA 22942, (540) 406-1313
Keswick Vineyards
1575 Keswick Winery Drive, Keswick, VA 22947, (434) 244-3341
Castle Hill Cider Llc
6065 Turkey Sag Road, Keswick, VA 22947, (434) 296-0047