After obtaining the tram ticket and opening the gate, you are attacked by a lot of Screamers. Because of their numbers, it is recommended that you make a run for it rather than to try and fight them. The tram is on the building just across from you, the one with the blue sign that says "The Souvenir Shop". Climb up and go through the double door. Close the door behind you, then go to the machine near the rotating door, and open your inventory. Use the following item:
Free Ticket
Ticket for one free ride on the Devil's Pit Aerial Tram
You insert the ticket and go through the spinning door. Enter the Sky Tram, and you will ride it to Devil's Pit. This unlocks an achievement/trophy, "Out of the Frying Pan".
Exit the Sky Tram when you get to the other side. Your goal now is to find a way into town. The tram leaves, meaning you can not return to the area you were just in, with the diner and the motel. Open the double door and go down the stairs. Enter the train conductor room. There is static on the TV, and you can try to switch it off but it's no use. Open another door and find a first aid kit on the shelves. In a side room, on a wooden crate, you can find a lighter. There is a radio here which works and tunes to WLMN FM.
Notice the boarded door. Doesn't look like it would take much to knock it down. You can break that door with an axe or other metal weapon. There is a crowbar on the floor which you can use for this purpose. After you break the door open, go out into the courtyard and find yet another boarded door you can break. Enter the circuit room and get the key from the key rack, (in your inventory it will show up as "key from the tourist center").
Go back up to where the tram was, then use key on the exit door. There is another lighter on the desk there. Go outside to the terrace. There are some maps on the wall, of Devil's Pit, grab one of them. There will be a cutscene where you look down into the gorge, then notice someone. He tells you this place used to be filled with tourists and visitors. He introduces himself as JP, and tells you that this is the Devil's Pit, four hundred ninety meters straight down to the blackest soul of the earth, the deepest limestone sink hole north of the... You interrupt him and tell him that someone or something tried to kill you back there and ask him if he had seen anyone strange wandering around here. You ask him about a quick way out of here. He tells you that a way out would not do any good for you. As you are about to leave, he tells you that if you head through the cavern there is a train, can take you to Hillside.
You ask him if he can show you the way, but he says there is some place he gotta be. You thank him for the tip.