This popular hiking trail and trailhead is located within the Terry Badlands Wilderness Study Area (WSA). This is a great day hike, which is a little over 1 mile to get to the natural bridges, and is a relatively easy to moderate hike. To get to the Natural Bridges trailhead, you must first traverse the Calyspo Trail via a four wheel drive vehicle. A small sign is located within the WSA to mark which way the trailhead is located. Wheeled traffic is restricted to the Calypso Trail only, as both sides of the trail are part of the WSA. An interpretive sign marks the beginning of the Calypso Trail, which provides this road access to the picturesque Terry Badlands Wilderness Study Area and the Natural Bridges recreational trail.

From Terry, take Old Highway 10 west of Terry for two miles, turn right onto the Milwaukee road. You will need to cross an old railroad bridge, one-way traffic only. After crossing the truss bridge, the Calypso Trail will start on your right hand side, follow it to the left by the interpretive sign – if you continue right you will go to the Calypso Special Recreation Management Area next to the Yellowstone River.