GetHiking! Charlottesville (Charlottesville, VA)

The 44.4-mile Washington and Old Dominion Trail (W&OD), one of suburban Washington, D.C.’s most popular rail-­trails, is a fantastic link between the state’s rural and historical past and the nation’s capital.

The trail is paved and exceptionally well marked, with mileposts every 0.5 mile and interpretive signs telling the story of the people and places along the rail line. The first 10 miles of the W&OD trail, stretching from Purcellville (western endpoint) to the historic town of Leesburg, travel through the rolling hills of Virginia Piedmont farmland. Horses graze, cornfields flourish, and trail crowds thin out somewhat.
As the trail continues, it passes through Sterling and Ashburn, which features a year-round trailside barbecue restaurant. The town of Herndon features an old caboose, as well as a trailside train depot, used as a visitor center.
The wooded trail surroundings feel a bit more suburban as the path continues through to the communities of Reston and Vienna. In Vienna, there is yet another caboose and train depot.

From west to east, the elevation gradually declines. The leafier suburbs quickly become more urban, as the W&OD Trail makes its way towards its eastern terminus in the unincorporated community of Shirlington in Arlington.

This will be a two-day ride. On Friday (5/29), we'll ride west from Sterling to Purcellville for 21 miles, have lunch along the way, and ride back to Sterling. Total distance of 42 miles. On Saturday (5/30), we'll ride east from Sterling to Shirlington for 23 miles, have lunch along the way, and ride back to Sterling. Total distance of 46 miles. These two rides are optional. You can choose to do just one or both.

Disclaimer: GetHiking Charlottesville Organizers are not professional guides. Expect the same risks and take the same precautions you would take if you were riding alone. With your RSVP, you agree with this disclaimer.

Weather: (as of 5/28/2026)
Fri (5/29): High 80F, sunny.
11 am - 69F, sunny.
1 pm - 73F, sunny.
3 pm - 77F, sunny.
Sat (5/30): High 72F, mostly sunny.
9 am - 64F, sunny.
11 am - 65F, sunny.
1 pm - 69F, sunny.

Notes:
1. This is a no drop ride. Pace is 10-14 mph. At each crossing on the trail that's controlled by a stop sign or light, we will stop and consolidate the group on the other side of the trail.
2. Reference guide: https://www.traillink.com/trail/washington-and-old-dominion-railroad-regional-park-(wod)/.
2. Mandatory equipment: helmet, repair kit/spare tube/pump.
3. Suggested trip equipment: cool-weather gear, cash, cell phone, ID/car keys, sunglasses, snack/drink, cable lock. Leave change of clothes and water (for rinsing) in your vehicle.
4. A final itinerary or cancellation notice will be posted 3-5 days before the ride.

Final Itinerary: All events are optional and subject to change. Times are approximate.
Friday (5/29):
10:30 am - meet at Sterling/Pacific Boulevard Washington & Old Dominion Trail Parking Lot for start of ride and group introduction.
11 am - ride west to Purcellville for 21 miles, have lunch at Magnolias at the Mill (198 N 21st St, Purcellville), and return to Sterling for another 21 miles. Total - 42 miles.
4 pm - check-in at local hotels. I have a reservation at TownPlace Suites by Marriott Dulles Airport, 22744 Holiday Park Dr, Sterling.
5:30 pm - meet for dinner at Siam Spice Thai Cuisine, Gordon Kitchen, 506 Shaw Rd # 329, Sterling.
Saturday (5/30):
8:30 am - meet at the same parking lot for the start of the ride.
9 am - ride east to Shirlington for 23 miles, have lunch at Weenie Beenie (2680 Shirlington Rd, Arlington), and return to Sterling for another 23 miles. Total - 46 miles.
3 pm - end of our 2-day adventure. And, drive safely home.

This hike feels like a compact Blue Ridge experience—not a single “wow” moment like a huge summit, but a steady sequence of smaller highlights: a tucked-away waterfall, quiet woodland loops, and a few rocky viewpoints.

This route—starting near the Humpback Rocks Picnic Area and linking Morgan’s Loop, Upper Shamokin Falls, and Cedar Cliffs— is one of those classic Blue Ridge Parkway hikes that packs a lot of variety into a relatively compact outing: waterfall, forest, ridgeline, rocky viewpoint, and some rugged terrain.

The trail includes some steep, uneven, and occasionally slippery sections, especially near the falls and on rocky terrain. Trekking poles and sturdy shoes are strongly recommended for stability and comfort.

Starting/Ending Point: Humpback Rocks Picnic Area (about MP 8.5) on Blue Ridge Parkway

• Take the Blue Ridge Parkway
• Turn into Humpback Rocks Picnic Area (about MP 8.5) Look for Sign. (This is not Humpback Rocks Parking Area)
• Go to the back parking lot near the AT Trailhead.

Please do not use a GPS pin—it may direct you to the wrong location.

Hike Distance: 6.5 Miles

Route: Start at the Humpback Rocks Picnic Area and take the connector trail to the Appalachian Trail. Head south toward the Wintergreen Resort, then pick up Morgan’s Loop, which leads down to Upper Shamokin Falls and continues toward Cedar Cliffs. From there, return by following the old AT alignment back to the current AT, and retrace your steps to the picnic area.

RSVP Expectations: If you are unable to attend, please update your RSVP to “No” as soon as possible. This allows hikers on the waitlist the opportunity to join.

Dog Policy: No dogs, please — we love them, but leave your furry friend at home.

Recommended Items: Broken-in Hiking Boots, Trekking Poles, Lunch/Snacks, 2-3 Liters of Water, Good Day Pack, Tick Repellent, Layers of Clothing for Spring Weather, and any additional items you need for comfort and safety.

Start Time: We begin our hikes on time. We may not have cell service at the trailhead. Please be on time.

Weather Policy: The hike may be canceled or postponed the day before if rain or icy trails are forecast. We’ll make the final decision by 7:00 a.m. on the morning of the hike and post updates in the comments. Steady rain with not much chance of clearing and/or dangerous conditions will call for postponing the hike.

Disclaimer: GetHiking Charlottesville’s organizers are not professional guides. Participants should expect the same risks as hiking independently and take appropriate precautions.
By RSVPing and attending, you acknowledge:

• You are solely responsible for your own safety and well-being.
• You are participating at your own risk.
• You will not hold the organizers liable for injury, loss, or damage arising from this event.