You mentioned Winchester VA above. I have enjoyed stopping over in that town, during my trips to Washington DC and to southern NJ.
On one of my trips, I found the State Arboretum of Virginia a half hour away on US Rt. 50. What a great place! They have a variety of gardens, but I was agape at the fine collection of conifers, many of which I had never seen growing in this part of the country. There is also a gridded out grove of Ginkgo, unusual in itself. This site is also the home of the Blandy Experimental Farm. It is well worth a stop.
https://blandy.virginia.edu/
You also mentioned Charlottesville, which isn't far off the Blue Ridge Parkway. A nifty site that isn't often known/visited is adjacent to the Parkway: Swannanoa. This was the summer home of the folks that built the Maymont estate that is now a city park in Richmond. It has had a storied life through the 20th century, with ups and downs. It has the biggest Tricolor Beech I've ever seen, and interesting architecture.
https://skyline-swannanoa-inc....
You are all probably well aware that there are a plethora of vineyards/wineries in this area, and many fine places to eat as well. Way back 30 years ago when I first visited this area, it was on a trip to Fishersville to buy a swath of fine perennials from Andre Viette Nursery.
https://inthegardenradio.com/
