the most beautiful virginia road trip
Virginia is a state that offers so much. It has the mountains, the sea, some large cities, gorgeous rural towns, and gosh – so full of history. It’s one of our favorite destinations and this was one of our favorite fall trips ever. Here is what we did and some other tips if you find yourself in the area.
what part of virginia?
Southwestern and central Virginia is the area we visited. We were mainly in Roanoke, Natural Bridge, Staunton, Wintergreen Resort, and Charlottesville.
We stayed in Wintergreen Resort which was a great home base because all these other things are just about an hour from there. In our search we found staying in Charlottesville to be very expensive for a group of our size (11 adults and 4 kids) so staying out a little farther is more affordable and beautiful because this area is in the mountains!
what to do
These are the things we prioritized and a few others we wished we could’ve done but didn’t have time for.
NATURAL BRIDGE | A Virginia State Park with a naturally occurring 200-foot bridge that will stop you in your tracks. There are some trails for hiking and a visitor’s center. We spent about 2-2.5 hours here.
NEARBY NATURAL BRIDGE | There are lots of other attractions nearby: Virginia Safari Park, Dinosaur Kingdom, Natural Bridge Caverns, and the Natural Bridge Zoo.
FARMS + MORE | We found an Asian Pear orchard/you-pick flower farm/wine tasting room and that was the obvious next spot for us! Virginia Gold Orchard is beautiful so 10/10 recommend going there as long as fruit and flowers are in season.
hiking
Staying in the Wintergreen area means you’re by the Blue Ridge Parkway and just a few miles to the southern entrance to Shenandoah National Park. We did the popular Humpback Rocks hike (the long version) which was plenty for the kids and adults. There are dozens of other hikes within a span of 10-15 miles so if you want others then just check AllTrails for more options.
OTHER THINGS THAT LOOKED COOL IN THIS AREA | These are the other things I had saved to explore if we had time: Blue Ridge Tunnel, Frontier Culture Museum, Summer Tubing at Wintergreen.
charlottesville + monticello
Visiting Monticello, like any other plantation or site built on chattel slavery is a somber experience. There is a 45-minute house tour that then allows for free roaming of the grounds and other exhibits. There are several other tour options including a gardens/grounds-only tour that might be best for kids who can’t handle the guided tour.
THE DAIRY MARKET | We just love food halls and Charlottesville has a cool one.
WHAT ELSE WE HAD OUR EYE ON | This immersive art experience called The Looking Glass looked neat. The park itself wasn’t as much of a hit as I’d hoped, maybe if/when there are other events happening! The historic downtown looks like a great place to stroll but we ran out of time for that. We heard Carter Mountain over and over again as a great place for apple picking too.
wineries, Breweries & distilleries
I was surprised to see so many of these! On the drive from Wintergreen to Charlottesville we probably passed 15. They all looked so great. Here is a guide to the breweries and distilleries and the wineries.
other parts of virginia
Roanoke isn’t far and has lots to explore. Check out this kid-friendly section of their website for ideas. I also keep my eye on The West End Mom for all things in Richmond (on the east side of Charlottesville).
If you haven’t considered a road trip to Virginia before then I hope this opened up new ideas!
