Its proximity to the eastern Blue Ridge provides the Charlottesville region with some special and challenging climbs up from the valley on either side. Here is a list of most of the major climbs up to the Blue Ridge near Charlottesville. Almost all of the roads on these climbs are in excellent condition. Note that the Shenandoah Valley is about 500-600 feet higher than western Albemarle County, so the climbs from the west are generally shorter than from the east (although some of them are particularly steep).
The climb to Afton Mountain (1900 feet elevation) from the east is moderately challenging but is probably the easiest climb up to the Blue Ridge from that side. It includes 1.5 miles on US 250, but the road is two lanes going up and is considered safe. This climb is part of the Afton - Sherando - Waynesboro route.
Reeds Gap (East)
Beech Grove Road (Route 664) climbs up to mile 13.5 on the Parkway from the east. A relentlessly increasing grade with no breaks makes this a very challenging climb, as much mentally as physically. Local tradition has it that early in his career, Lance Armstrong had to climb it during a race and later complained that it was "too steep for competition".
Wintergreen (aka Devil's Knob)
Beech Grove Road (Route 664) climbs up to the Wintergreen Resort. This follows the same route as Reeds Gap (East) to a mile from the top, then turns into the Wintergreen Resort community and continues up to the top of Devil's Knob. This the highest climb in vertical feet of any in the area; much of it is very steep, and it is more shady than the Reeds Gap climb. Wintergreen has a long history of welcoming cyclists, but remember that it is a private resort; please use it with appropriate consideration.
Reeds Gap (West)
Reeds Gap Road (Route 664) climbs up to mile 13.5 on the Parkway from the west. Shorter than the east side climb, it nonetheless has some very steep sections.
Love Road (Route 814) climbs up to Mile 16.1 on the Parkway from Sherando valley on the north/west side. This climb is steady and very scenic, and not as steep as most of the other climbs listed here.
Crabtree Falls Highway (Route 56) climbs up to Mile 27 on the Parkway from the east. This is a quite long, moderately to very steep climb that ascends in more of a stair-step fashion compared to the other climbs. It is very scenic and shady, following the Tye River and other streams for a good part of its course. There is a store at Montebello, about three-quarters of the way up. This climb is on the Crabtree Falls - Devils Knob route.
The Tye River Turnpike (Route 56) climbs up to Mile 27 on the Parkway from the west. Shortly after leaving the town of Vesuvius, the route begins to climb steeply and steadily for 2 miles, then the grade moderates somewhat as it reaches the Parkway. This is a truly beautiful experience, part of the TransAmerica Bike Route, and is not to be missed. This climb is on the Humpback Rocks - Vesuvius route.