Woods-Upland Trail loop hike map (click to enlarge)

Length: .9-mile loop
Time: 30 minutes
Difficulty: Easy

A short loop hike through the interior of Theodore Roosevelt Island can be made by hiking the sections of the Woods and Upland trails that lie south of the Roosevelt Memorial. As with any hike at the park, this one starts at the end of the footbridge that leads to the island from the Virginia mainland. Take a right on the wide, gravel path—the Swamp Trail—that you find yourself on as soon as you come off the bridge. To get your bearings, there is a trail map posted on a bulletin board. Take a photo of it with your phone and refer to it as you hike, because there are no directional signs posted at any intersections.

You don’t get fifty yards before you come to the intersection with the Woods Trail, which forks off to the left. No sooner do you turn than the trail splits again, this time with the left fork branching off towards the Roosevelt Memorial. Stay right to remain on the Woods Trail and continue towards the southern end of the island.

Like all of the original trails designed by landscape architect Frederick Law Olmsted Jr., son of the famed Frederick Olmsted Sr., the Woods Trail is a wide gravel path that is largely free of rocks and roots on the surface. It remains shaded for its entire quarter-mile length.

Typical terrain of the Woods Trail, Theodore Roosevelt Island

The Woods Trail ends by merging into the Swamp Trail, though because it is a V-shaped intersection with the Swamp Trail coming in at a sharp angle to your rear, you may not even notice that you changed trails. Just keep hiking straight until you reach the restroom building.

The restroom is the only building that has been on the island since it became a park. It was always part of Olmsted’s plan, dating back to the 1930s, but it wasn’t built until the mid-1950s. It is usually open from April though September. When closed, there is a portable toilet located near the building.

Restroom at the southern end of Theodore Roosevelt Island

The trail forks once again just past the restroom. The path to the left leads up a moderate hill to the Upland Trail, which is your next destination. Stay straight if you want to remain on the Swamp Trail.

Connector to the Upland Trail on Theodore Roosevelt Island

The Upland Trail is what I call a lollipop trail, meaning that you hike out on a stick before coming to the loop, then hike around the loop and return back to the start on the stick. On this hike you are joining the trail at the far end of the loop and will only hike the eastern half of it before hitting the intersection with the stick and returning back to the start, which in this case is the Roosevelt Memorial. I took a right at the intersection of the connector trail and the Upland Trail and hiked the loop in the counterclockwise direction.

The Upland Trail, and the Woods Trail for that matter, is a typical nature trail. At one point there must have been a brochure to go along with it for there are numbered posts that mark spots where you could read information about the history of the island or about the plants and animals you might find at a particular location. However, there is no longer a National Park Service Ranger presence on the island, so if such a brochure still exists—which I doubt—I wouldn’t have a clue as to where to find one. In lieu of the printed brochure, there are a few signs posted on the side of the trail that note the history of the island and its native plants and animals.

Typical terrain of the Upland Trail and the #8 post along the trail

Other than walking through the woods on a wide and smooth-surfaced trail, there’s not much to the Upland Trail. The only thing of interest would have been the ruins of the old John Mason mansion, but those behind the park’s creation decided to remove the house and outbuildings when the island was originally landscaped. Any below ground features were buried. Mason was the son of George Mason, one of the founding fathers of the United States (there is a memorial to him just off the National Mall near the Jefferson Memorial). When it came time to make a decision about preserving the mansion, some people felt that John Mason was not a significant historical figure, plus his son ended up being an instrumental part of the Confederate uprising during the Civil War, so they didn’t want his legacy preserved on an island that was supposed to be a memorial to Roosevelt.

Information sign about the John Mason estate

The next intersection you come to is the point at which the stick portion of the trail begins. This is another one of those V-shaped mergers, so just keep hiking straight to get back to the Roosevelt Memorial. The Upland Trail continues past the memorial and eventually dead ends into the Swamp Trail at the north end of the island, but since I already hiked the Swamp Trail earlier, I decided to end my hike at the memorial. There is no official trail that connects the Upland Trail back with the Woods Trail at this point, so just cut across the memorial to the west side and look for any trail that heads downhill. These will lead back to the footbridge.

Unless you just want to hike all of the trails on Theodore Roosevelt Island, there’s no reason to hike the Woods Trail or the Upland Trail. The only hike worth your time is the Swamp Trail, for it is the longest possible hike, and it passes through the scenic marsh. The Woods and Upland Trails pass through nothing but forest. If the Mason house still stood, that would be something worth seeing, but without it the hike is completely uneventful.

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