Tuscarora Trail: Hike to Pinnacle Overlook & Pinnacle Shelter in Winchester, Virginia

I recently hiked a section of the blue-blazed Tuscarora Trail in Winchester to Pinnacle Shelter and Pinnacle Overlook. It was not easy, but it was a great hike.

The trailhead is located in the Shawneeland neighborhood, which is situated on a small mountain. You drive up and up and up to reach Timber Ridge Trail.

Timber Ridge Trail is not an actual trail. All the roads in Shawneeland are called trails, including Maple Trail, Timber Ridge Trail and Fir Trail. Yes, all roads.

Once you reach the trailhead, you are near the top of the mountain, so of course, the hike begins with a descent. As in, nearly 600 feet over the course of one mile.

Trail Stats 
Length5.6 miles
DifficultyStrenuous
Trail TypeLollipop
Elevation Gain1,365 feet
Duration4-5 hours
TerrainMostly dirt and rock trails, some grass and rock scrambles
Dog-FriendlyYes
FeeFree
Driving DirectionsClick Here

Biby Wilderness Trail

Since the trailhead is located in a neighborhood, there is no parking lot. Instead, you park parallel on Timber Ridge Trail where it meets Rockwood Trail.

You’ll see a double white blaze on a telephone pole and a small sign for the Biby Wilderness Trail. This 0.7-mile hiking trail leads to the Tuscarora Trail.

At the trailhead, you’ll be in full sun, but not to worry. You will quickly enter the woods and will be in nearly full shade for the majority of the hike.

You will see a mostly grassy trail to the right of the Biby Wilderness Trail sign. Before you take your first steps, enjoy the mountain views in the distance.

From here, begin your descent along the rocky switchback-laden trail. Take it slow on this white-blazed trail. You don’t want to miss the Allegheny View.

Allegheny View

At the .3-mile mark, you will reach a sign for the Allegheny View and a yellow-blazed spur trail. Turn left here for a rock scramble and a mountain view.

The view was pleasant, but it was also obstructed by leaves, so it may be better in late-fall or winter. The rock scramble is fun but it does not better the view.

As in, the view doesn’t improve the further down you go on the rock scramble. The best view is from the top of the scramble.

Re-trace your steps to the Biby Wilderness Trail, then turn left to continue along the switchback trail until you reach the Tuscarora Trail.

Tuscarora Trail 

At the trail sign, turn left onto the southbound section of the 252-mile Tuscarora Trail. You’ll find the hiking trail is mostly dirt and rocks, often way more rocks.

At the 1.0-mile mark, you will reach the second of several rock scrambles. This time of year, the fragrant mountain laurel is out in full force all along the trail, too.

The ascent now begins, but really, you go up a little, walk a flat section, go down, then back up again, then walk once more on a flat section.

You’ll arrive at a platform at the 1.8-mile mark. It looks like a zipline platform, but to be clear, there is no zipline. I really don’t know its use. Unusual.

In a few more steps, you’ll start to hear moving water, then an easy-to-miss spur trail turns up on the right at the 1.9-mile mark. This leads to a small waterfall.

The waterfall was nice, but it wasn’t much more than a trickle on this warm summer day. There is also a fire ring. It was definitely worth a quick diversion.

Pinnacle Shelter 

At the 2.2-mile mark, the trail splits, but you’ll want to stay right for the Tuscarora Trail. In a few more steps, you will reach the Pinnacle Shelter.

Turn right onto the spur trail to reach the three-sided Pinnacle Shelter. There is also a picnic shelter, two stone fire pits (one for cooking) and an outdoor privy.

From here, re-trace your steps to the Tuscarora Trail or continue walking on the path that runs behind the shelter. Both routes re-connect with the hiking trail.

Once you reach the Tuscarora Trail, turn right to continue on to the Pinnacle Overlook, which turns up on the right at the 2.9-mile mark.

Pinnacle Overlook 

It’s a beautiful rocky overlook with far-reaching mountain views. There are several overlooks, too. I personally thought the third one had the most superior vistas.

To the left of the overlook, you will see a white-blazed trail, which basically runs parallel to the Tuscarora Trail, but also runs alongside several more overlooks.

In a few more steps, this white-blazed trail will re-connect with the blue-blazed Tuscarora Trail. Then, at the 3.0-mile mark, a trail sign. Turn left for Pinnacle Camp.

At Pinnacle Camp, you’ll find a flat and well-shaded area that’s just right for pitching a tent and creating a campfire. There’s plenty of room for everyone, too.

Re-trace your steps to the trail, then turn left to continue on. In a few more steps, you will exit the forest and reach a graffiti-laden powerline clearing with views.

Stay to the left and you will re-enter the forest by way of the yellow-blazed Frye Path. Keep your eyes open, it is easy to walk on by (I missed it the first time).

Laurel Run Trail 

At the 3.5-mile mark, stay left for the white-blazed Laurel Run Trail. This trail soon re-connects with the blue-blazed Tuscarora Trail. Turn right when it does.

Re-trace your steps on the Tuscarora Trail and Biby Wilderness Trail to reach your vehicle. Don’t forget, the last mile is nearly all uphill until the end.

Wrap-Up Notes

From my car, this Shenandoah Valley hike took me just over three hours, including time spent exploring Pinnacle Shelter and Pinnacle Overlook.

As much as I enjoyed one of the top hikes near Winchester, the rocks scrambles were a drag at times. They definitely encourage you to take it slow though.

Despite the 90+ degree day, the temps at the top and along the hike were manageable. In full sun at the overlook, I was comfortable. Carry lots of water.