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Henley Hollow Trail is a 8.2 mile lightly trafficked out and back trail located near Speedwell, Virginia that features a waterfall and is rated as moderate. The trail offers a number of activity options and is accessible year-round. Dogs and horses are also able to use this trail.

8.2 miles
1,742 feet
Out & Back

dog friendly


horseback riding

mountain biking

nature trips


bird watching





wild flowers


A nice trail that follows a creek then winds up the mountain past a very small but nice waterfall and up onto the ridge line ending at the horse trail. Little Dry Run Trailhead is just on the other side of the highway. You can do the 11 mile loop which connects three trails, the Highlands Horse Trail, Little Dry Run Trail, and Henley Hollow Trail.

Monday, December 25, 2017

Another review... You can complete a 14.8 mile loop hike by hiking up the Henley Hollow Trail, then turning right onto the Virginia Highlands Horse Trail. Once you get to FS14 turn right then hang a left and hike up the Dry Run Gap Trail. Some of this trail is the old road bed of Hwy 21. You will see a couple of old concrete bridges along the way. Continue on by turning left onto the Iron Mountain Trail to it's end at the Divide Trail, which takes you down the mountain back to Forest Service Road (FS14) which is where you will jump back onto the Virginia Highlands Horse Trail which will take you up to Horse Heaven and then back to the Henley Hollow Trail.

Wednesday, November 29, 2017

Nice trail that has a very small waterfall (sometimes a drip) close to the top of the ridge. Trail starts next to Hwy 21 and ends at the Horse Trail (Dirt Road) on the ridge top. Take the Horse Trail to the left to an area called Horse Heaven or turn right and hike down to the CC Camp Road and folllow it to the right to Hwy 21. You can remain on the Horse Trail from the ridge top and follow it across Hwy 21 to Little Dry Run Trail which will take you back down to the Henley Hollow Trailhead. Total loop is between 11 & 12 miles.

Wednesday, June 07, 2017

nice hidden gem. trail comes to a clearing with a dirt road, not sure where road leads to, turned around and went back. trail seemed to be like 4 miles in and out!! Several small streams you will need to pass

Sunday, July 24, 2016

About a 600 ft. Elevation change over the 2 mile point to point trail. Trail used for horseback riding, mountain biking and hiking. Trail ends at a junction with a horse trail.

25 days ago

Sunday, October 15, 2017

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