The Saunders-Monticello Trail
Distance: about 4 miles round-trip
Biking: yes (better suited for mountain bikes; trail closes to bicycles in inclement weather)
Dogs: no (dogs are allowed on the secluded farm trails, but only on a very small portion of the Monticello trail)
Kid friendly: yes
Wheelchair/stroller accessible: yes
Once I discovered this trail, I couldn’t believe that I had lived in Charlottesville for so long without knowing about it. It is now one of my favorite running spots and I take all of my out-of-town company there to show it off.
If you park in the large parking lot off Route 20, the trail takes you under Route 53.
After you cross back over 53 via Saunders bridge, you continue through the Monticello gate, past the picnic area on your right to the end of the trail. The trail ends at the Monticello bus parking area. If you wish, you can continue across the parking lot and visit the Monticello store and museum. Or, you can turn around and head back to your car. If you arrive at the Monticello gate before operating hours (as I usually do) you will be greeted by a Monticello employee who will politely tell you that you need to turn around.
Directions from Charlottesville:
Take Route 20 South out of town. You will pass Piedmont Virginia Community College on your right and the Trail at Monticello parking area on your left. You will have to make a U-turn at the intersection of 53 and backtrack to the Trail at Monticello parking area, which will now be on your right.
(***update: It was just brought to my attention that it is now illegal to make a U-turn at the intersection with 53. You can make a left, then turn around in the small parking lot on the right to get back to the larger lot off of 20. You could also take Avon Street Extended South out of Charlottesville, then turn left onto Mill Creek Drive just after the Food Lion. This way, you will pass Monticello High School on your left, then make a left onto Route 20 at the traffic signal. Going this way, you will continue straight through the intersection with 53, then turn right into the large parking lot pictured below.)
There is an additional (much smaller) parking lot on Route 53. If you park at this lot and, facing the trail, choose the path to your right, it is exactly 4 miles round-trip to the Monticello bus lot and back. If you take the path to your left, you will finish just shy of 4 miles.
You can also access a network of singletrack trails from here.