Rocky Mount Trail Loop in Shenandoah National Park is a roughly 10 mile dog-friendly loop offers great views from the ridgeline and stunning wildflowers in the spring and fall colors in October and November.
The trail begin 0.1 miles north of Two Mile Run Overlook at milepost 76.2 on Skyline Drive. You can park at this overlook for the night, just make sure you fill out a (free) wilderness permit and walk the short way on Skyline Drive to the trailhead.
Immediately climb a wooded knoll before heading northeast on a ridgeline. Reach a trail junction at 2.2 miles and take a left towards the summit of Rocky Mount. At mile 3.3 there is a small trail to the left that leads out to an amazing view of the Blue Ridge and the Shenandoah River to the right.
You will summit Rocky Mount at 2,741 feet and then begin your descent on a lesser-used trail. At 4.6 miles you will reach a tributary of Gap Run and rock-hop two streams. There are good campsites on the flats of Gap Run, or you can find a good spot near the summit if you are overnighting it. Just keep in mind there are no "official" spots so you will have to get creative.
Follow the blue blazes until you reach mile 6 and and another trail signpost. At mile 7.6 you will reach the first junction in the trail where you will retrace your steps 2.2 miles back to Skyline Drive. The entire loop is 9.8 miles with 2,200' elevation gain and well marked.