Devil’s Sentry Box at Castillo San Cristóbal, San Juan National Historic Site

Length:  .4 mile, one way, from Castillo San Cristóbal (.8 mile round trip)
Time: 45 minutes (round trip) with time to take photos
Difficulty:  Easy cardiovascular-wise, but the terrain is a little rough

When visiting Castillo San Cristóbal, head up to the main terreplein (park signage calls it the Main Firing Battery) and look for a small turret that juts out from the fort wall. This is called a sentry box, and visitors to the fort are allowed to go inside. Once there, look down towards the ocean shore and you will see another sentry box, Fuerte del Espigón (Fort of the Point, aka Devil’s Sentry Box). This sentry box gets its name for a solider (or soldiers, depending on who is telling the story) who supposedly disappeared one night while standing watch, and now his ghost haunts the place. The devil had taken him.

The Devil’s Sentry Box is one of the few features of the original San Cristóbal that remains today. Most people do not even know it exists, and even fewer know that they can get down to it. If you are a photographer or just want some great photos, this is the place to be.

Devil’s Sentry Box at Castillo San Cristóbal, San Juan National Historic Site

Fuerte del Espigón was no longer used after 1880, and it fell into disrepair. In 2005, a major restoration was done by the National Park Service, and today visitors can hike to the sentry box provided they know where to go. The National Park Service does not actively promote the hike, and some of the Rangers don’t even know about it. One gave me some wacky directions that I knew didn’t sound right, so I asked another Ranger and got the straight story.

It is not a difficult hike, and there is an actual trail, but you may possibly be traveling through very tall grass because the National Park Service does not maintain the trail on a regular basis. The Ranger who provided me with directions said that she wasn’t even sure if I would be able to get through. She also said the Rangers had been talking about weed whacking the area, but who knows if this will ever get done. All I can say is that I didn’t come in contact with any ticks, spiders, chiggers, or other bugs, poison ivy, razor sharp grass, or briers. I did the hike in shorts—I was in Puerto Rico, after all—so I wasn’t really prepared. I do, however, recommend long pants if you are planning in advance.

To get to the Devil’s Sentry Box from Castillo San Cristóbal, walk out to the main road, Calle Norzagaray, and take a right (there is a sidewalk along the road). You will first pass another fort-like structure, the Bastión de San Sebastián (part of the original city wall), and once past that you will see a basketball court and a bunch of houses. That’s where you must get to, but you have to keep walking down the road until you come to a stairway that leads down below, then backtrack to the basketball court.

Basketball court next to Bastión de San Sebastián in San Juan, Puerto Rico

Staircase to the basketball court just west of Castillo San Cristóbal

There is a street that runs in front of the bastion that eventually becomes a sidewalk. Follow that until it ends.

Walkway at the base of Bastión de San Sebastián just west of Castillo San Cristóbal in San Juan

The trail starts at the end of the sidewalk. There is actually a gravel path, but the grass is so tall—five feet tall in places—that you can barely see it. However, despite how overgrown things were when I visited, enough people hike to the sentry box that a faint path through the grass stays visible, plus if you look at your feet you will see the gravel.

Trail to the Devil’s Sentry Box at Castillo San Cristóbal, San Juan National Historic Site

Tall grass on the trail to the Devil’s Sentry Box at Castillo San Cristóbal, San Juan National Historic Site

It only takes a couple minutes to get through the grass. The trail then continues into a thicket of some sort of shrub that forms a tunnel.

Thicket of shrubs on the trail to the Devil’s Sentry Box at Castillo San Cristóbal, San Juan National Historic Site

Once beyond the shrubs, the trail follows along a cliff, and the surface slopes steeply left to right, making it a little tough to walk on. It is very close to the cliff and extremely narrow, so I was surprised that the area wasn’t closed. Perhaps this is why the National Park Service doesn’t promote the hike.

Cliffside section of the trail to the Devil’s Sentry Box at Castillo San Cristóbal, San Juan National Historic Site

Then just like that, the trail becomes a well-manicured grass path that leads right to the sentry box. Now it’s time to take photos.

Final section of the trail to the Devil’s Sentry Box at Castillo San Cristóbal, San Juan National Historic Site

Devil’s Sentry Box at Castillo San Cristóbal, San Juan National Historic Site

Devil’s Sentry Box at Castillo San Cristóbal, San Juan National Historic Site

View of Castillo San Cristóbal from the Devil’s Sentry Box, San Juan National Historic Site

If you are at San Cristóbal and haven’t seen Castillo San Felipe del Morro (aka El Morro), the other fort at San Juan National Historic Site, the walk between the two is about a mile (same sidewalk). I suggest hiking to the Devil’s Sentry Box after you are finished at San Cristóbal, then just continue west to El Morro. No sense in walking back to San Cristóbal to finish sightseeing and then have to start all over again towards El Morro.

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