Prettyboy Dam Loop

Starting from the south side of the old bridge at Masemore Rd, head west along Gunpowder South Trail (White). The trail is narrow and a bit overgrown, but super idyllic and peaceful. You may find people fly fishing in the river. It isn't long before it becomes more technical as you come up on some huge rocks that you have to manage over for the foreseeable future. If unsure of the path, err on the side of staying along the water. There are ample huge rocks in the shade in the river, so taking a snack break to enjoy the moment is a must.Up and down over the rocks you'll go, and the trail will have you put in a little elevation while you duck branches then back down by the water. Just as you get tired, the air will start to feel cooler as you get closer to the dam - it's mist being a nice reprise on a hot day. At the dam, you can scale up a steep bit of final trail if you want, but not much of a view - do it anyway because why not. After you are done taking in the view of the dam, head back the way you came until you get to a small water crossing, then head right (south) and take the Highland Trail back. It's a beautiful wild forest along a small creek, but then you scale up to the top and have a nice smooth hike back through the forest before making your way back down to the Gunpowder South Trail (White) and back out to Masemore Rd. At a non-aggressive steady pace, the 4.5 miles should take about 2-2.5 hours. Recommend some hiking boots to take care of your ankles, poles if you are uneasy on rocks (and for the couple short bits of elevation), and bug spray if it's warm out. There's some parking at the bridge at Masemore Rd and Gunpowder South Trail (White) here https://goo.gl/maps/9etUgJGp6JY61kEe9 - maybe about 10 cars worth. Not sure how busy this parking lot gets versus others near by.