Downtown Charlottesville is a 25-minute drive from the southern end of Shenandoah National Park and the northern end of the Blue Ridge Parkway. It costs $30 per vehicle ($25 per motorcycle) to enter Shenandoah National Park, but the fee is well worth it. Because access is somewhat limited, the trails are that much better preserved. Generally there is less traffic on Skyline Drive than on the Blue Ridge Parkway. Backups on either road are extremely rare.
Entrance to the Blue Ridge Parkway is free. Both Skyline Drive and the Blue Ridge Parkway are popular among cyclists and motorcyclists. But you can't see the best views from the road. For the highest peaks, most dramatic overlooks and sunsets, toughest climbs, and best experiences, take to the trails detailed below.
Humpback Rocks Trail
This is the most talked-about hike in the area. It's hard to find a longtime local who hasn't made the climb. The vast majority of UVA students see the rocks before they graduate. To get there, drive west out of Charlottesville, hop on the Blue Ridge Parkway, and head south. The drive won't take more than 35 minutes.
Expect a short, steep climb--one mile, 700 feet up. Just enough of a challenge to make the view feel earned. The Rocks are a popular sunrise/sunset spot. The Humpback Rocks Trail intersects with the Appalachian Trail. Add an out-and-back leg on the AT to add miles to this hike.
Perhaps the best trail off Skyline Drive is Riprap Trail. It takes about 45 minutes to drive to the Riprap Trail parking lot from downtown Charlottesville. Remember that the entry fee to Shenandoah National Park is $30 per vehicle, a fee which will grant unlimited access to the park for a full week. The hike out to the ridge and back is not very strenuous. Expect broad views of the Shenandoah Valley there. The exposed rock along the ridgeline is beautiful and, for the young and young at heart, fun to play on. The entire loop is a little over 9 miles and should take 5 or 6 hours to complete. However, hiking out to the ridge and back is far shorter--more like 2.5 miles.
Rivanna River Trails
There are many ways to enjoy the trails along the Rivanna River. These wide, paved paths are perfect for hiking, running or bicycling. Most of this trail system is within Charlottesville's city limits. Access points can be found a mile or two away from the Downtown Mall.
Sugar Hollow is one of the most popular hikes in the area during the summer months. The trail ends at a cluster of swimming holes! Park near the end of Sugar Hollow Road, the closest vehicle access to the trailhead. You'll be near a river for a good portion of the hike, and hugging a mountain most of the way. An excellent loop--especially if it's warm enough to swim.
Ivy Creek Natural Area
The Ivy Creek Natural Area in Albemarle County offers a range of trails, each of which are relatively flat. You can bring your children, but you can't bring your dog (or any other pets, for that matter). Though this area is beautiful and natural, you won't be hiking in the mountains. If you think mountains look prettiest when they're not underfoot, this is the place for you.
The Saunders-Monticello Trail's popularity is its only flaw. Arrive very early in the morning for an optimal experience.
The main section of the trail is just over two miles long, and is beautiful throughout the year.
For a full understanding of what makes the trail so great, you'll need to experience it for yourself. Highlights include sweeping views of Charlottesville and Albemarle County (especially when the trees are bare) and access to a wide network of narrower paths, some of which lead as high as the edge of Carter Mountain Orchard.
Highland Rustic Trails
Just over the mountain from the Saunders-Monticello Trail are the Highland Rustic Trails: a system of rolling, scenic trails adjacent to the historic home of James Monroe. Be sure to tour the historic properties of James Monroe's Highland while you're there. Click here for a full map of the trail system.
These are, of course, but a few highlights. Dozens of trails crisscross the city and county. Neither are pleasant walks within the city limits--through grounds or along the Downtown Mall--detailed above. For more things to do for free in Charlottesville and Albemarle County, click here.
Winter Hiking Tips
Many enjoy hiking the trails above in winter. In winter, there are no bugs to worry about. The sun is less harsh (though sunscreen is still advised for longer winter hikes). Be sure to wear layers and avoid cotton fabrics. Woolen or synthetic layers dry much faster. This is why most hiking socks are made of wool. If you plan to hike at higher altitudes--Riprap or Humpback, perhaps--hand or toe warmers are strongly advised, especially in January and February. When hiking in colder weather, it's important to stay warm rather than get warm. From the heat of your car to the summit of your chosen mountain, bring what you need in order to keep the cold at bay.