The park is divided into two parts. The main front part of the park is never investigated by the team, however the rear of the park is covered in trails that are very easy to get lost in. The most notable areas are
- A tunnel that leads out very shortly after entering and doesn't seem to have any practical purpose. For whatever reason, The Operator protects this tunnel viciously.
- A building with lots of wood (possibly being a lumber mill) that is in Entry #52.
- A tree that appears to be growing on top of a series of bricks.
- A small grove which leads to the tunnel and is unnoticeable at first glance.
- A boarded up cabin where Jay wakes up in Entry #62
Jay never does find any clues to help him fight The Operator, however the forest helps him see how incredibly dangerous Alex can be.
Entry #29 is the first appearance of Rosswood Park (unknown at the time), in which the cameraman on the footage (assumed to be Jay) happens to wander down a trail and locate a tunnel where he finds some blood, a blood spattered rock, and a bloody T-Shirt, all fresh. The Entry is deep in the hard drive of the his memory card labeled "NOENTRY", and the video cuts out just as the camera spots The Operator. As a result, Jay does some scouting to locate where this may have taken place, and in Entry #31, he locates Rosswood, but is unable to find the tunnel or any traces of what may have happened in the seventh month period when he lost his memory. Rosswood Park is also frequented by civilians as well, as at one point Jay is walking down the trails in Entry #31 and assumes he's being followed, however it is simply a man with his headphones in who just coincidentally happens to be going down the same trails.
Rosswood Park is never entered again by Jay of the present and is rather investigated by the tape cache he locates in Entry #34, where he goes through the woods multiple times as does Alex.
Entry #38 involves Jay and Alex walking down a trail, to which Alex begins telling him about bizarre executions, none of which amuses Jay. At one point Jay has to replace the tape, but cannot find the other tape that leads off on it. It's never stated if Rosswood is the location of these bizarre executions, or just atmosphere for Alex to explain something.
Entry #39 Alex tells Jay to meet him at Rosswood Park, and eventually Jay makes it there and sleeps in his car overnight, to which a figure that looks like The Operator peers into his car. The following day in Entry #40 Jay gets frustrated with the time that Alex is taking to show up, and heads into Rosswood by himself, only to locate a tree built on bricks that he focuses on for a bit, and The Operator. Jay drops his camera and runs, only for Hoody to have been in the woods and conveniently stroll out of the park with the camera and place it in Jay's car before Jay gets back, indicating that Tim and Hoody may have a good idea of the trails in the woods. When Alex shows up to Rosswood in Entry #42, he berates Jay for going in alone and for losing his camera, and Jay calls it quits for the day, so whatever Alex planned to show him in Rosswood never got stated for the day.
Entry #48 and #49 are the next time Rosswood resurfaces as a plot point, and this time Jay is following Alex. Entry #48 is shown from Jay's camera, while Entry #49 is from Alex's camera. Alex walks to the tunnel followed by Jay, and eventually Jay runs before he gets spotted. Alex then sits for a while before an unknown civilian wanders near the tunnel, and Alex kills him out of paranoia. After the kill, The Operator shows up and takes the body. It can be assumed that Entry #29 took place just after this event since the blood was still fresh, and therefore Jay must have gone back to investigate. After Alex gets in his car, he calls Jay telling him to meet him at the park tomorrow.
Entry #50 mostly has Jay and Alex wandering and talking, supposedly taking place both before and after the tape in Entry #38, and Alex stays behind as it gets dark in the woods. Tim shows up to which Jay gives chase but loses him at the tunnel, where the crime scene has been completely cleaned up, meaning Entry #29 takes place before Entry #50.
In Entry #52, Alex takes Jay and Jessica into the woods, and plans to shoot them both, however Tim shows up and tackles Alex, allowing Jay and Jessica to escape. They run from the park and continue to the the Hotel.
In Entry #62 it seems as if Jay is walking on a path through Rosswood park looking for Tim , when Tim/Masky begins chasing after him. Mild audio distortions beforehand indicate that The Operator may have been observing from a distance. Masky also causes distortion whenever he appears to the camera. Finally Jay is captured and Hoody turns off the camera. Jay wakes up an a part of Rosswood he has never been to inside an old boarded up cabin where he finds Tim awakening in the same clothing as Masky outside the cabin. Jay's camera was inexplicably placed in front of him and turned on before he woke up, probably by Hoody.
In Entry #63, Jay and Tim go to their respective cars after leaving the shack, and discuss when they will meet up again.
Entry #64 has Jay and Tim returning to Rosswood, and they look around the building where Alex tried to shoot Jay in Entry #52, but all they find is a bullet-sized hole in the ceiling. After ward, they search for the shack from Entry #62, but they fail to find anything, even though they cover a very wide area. They go to the Tunnel, and while they are searching, Jay gets a call from Alex saying simply "Leave, Now", which indicates that Alex has followed them. Shortly after this, Tim goes into a coughing fit, and The Operator appears. Jay tries to drag Tim away, but Tim tells Jay to leave. As the Operator comes closer, Jay flees all the way to his car. When Jay gets to his car, he finds Tim inside his own car. He tries to talk to Tim, but Tim does not respond, and simply drives away.
In Entry #65 shows Tim wandering Rosswood after getting attacked by the Operator, and he drives away after Jay calls his name (like in Entry #64)
Due to Alex being aware of their location, Jay and Tim decided to leave the Rosswood Park area.