Shepherd Mountain & Battle of Pilot Knob – Missouri

On the way to several sites in Missouri such as Johnson Shut-Ins or Taum Sauk Mountain, Nicole and I would always drive through the small town of Pilot Knob, Missouri. There is a sign in the center of town for the Shepherd Mountain Hiking Trail.  So on a super foggy, but unseasonably warm January day, we decided to check out this hiking trail.


From the parking lot, you are faced with the immediate decision to take the “steep” path or take the “less steep” path. Both will get you to the same place, the “less steep” option just adds a bit of distance.


Being that this was our first hike in quite a while, we opted for the “less steep” option which was still steep by the way =)


Once the trails join back up, there are several good overlooks of the small town below…except when it is foggy LOL!


We finally reached the summit!


The pups were super happy to be out on the trail after a long and really cold winter. Look how cute Dexter and Ellie look! P.S. Take a look at the mud on Dex…since this trail is fairly new, the ground is not hard packed like other trails. The ground was thawing so was extremely muddy.

Along the trail, you pass several signs noting different encampment spots during the Battle of Pilot Knob.

At one time they even tried to open a ski lift on the mountain and the remains still stand today.

After we finished up this trail, we headed over to the Battle of Pilot Knob State Historic Site. It is in the middle of town and visible from Shepherd Mountain. During the Civil War, the Union Army occupied Fort Davidson which stood at this location. The moat and dirt walls still stand.

In late 1864, the Confederates were perched on Shepherd Mountain and began to attack the fort. In the picture below, Fort Davidson sat in the depression and in the distance you can see Shepherd Mountain. You can read more on the history of the battle here!


There is also a beautiful grove of pines =) Props to Nicole for finding these cute pine cones!

In addition to the self-guided walk around the battlefield, there is one paved trail.

We took a quick walk around and noticed the pink granite that is very common in this part of Missouri. El decided to climb on the rock pile…


Overall, it felt great to get outside and hike. Be sure to check out these two sites! Also, I recently created a Facebook page so please follow me on Facebook, just search for Planned Spontaneity Hiking!

Categories: Battle of Pilot Knob, Shepherd MountainTags: , , , , , ,


  1. Thanks for sharing this adventure. We had spent some time not too far from there called Twin Rivers Landing. It is a beautiful area around there. So glad you were able to get outside in January. Love the pics and the history lesson!!!!


  2. Gorgeous pictures (again)!!


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