After leaving Rosewater Park, you’ll have free roam of Silent Hill again. There are a few places you need to go, and there are a few places you can go optionally. Maria will be with you the whole time. If you’re trying for the Maria (Ending), make sure she doesn’t get injured! If Maria dies, the game ends.
Jacks Inn is a small motel south of Rosewater Park. You can find a Save Square on the back of one of the cars.
If you have met the criteria, you can get the Dog Key around here. Across from the exit from the park is Jack’s Inn. Directly to the west of it is an empty lot with a doghouse in it. Search the doghouse to find the key and earn the achievement / trophy Man’s Best Friend.
Head West to Texxon Gas. Here you will find a car with a Steel Pipe in it still running. Take the pipe out of the car to add it to your inventory as a weapon.
Look around for a big white truck nearby. At the front of it will be some Handgun Bullets and Health Drinks.
On a second playthrough you can find the Book of Lost Memories. It will be on a white newsstand next to Texxon Gas Station. Grab it to earn the Not So Lost Memories achievement / trophy.
Head West of Texxon Gas to Pete’s Bowl-O-Rama. You can find a Health Drink on the sidewalk along Nathan Street.
Enter the Bowl-O-Rama through the door on the Northern part of the building. Enter the door for a short cut scene. Once inside, enter the door on the left for another cut scene.
After the scene, go through the door at the other end of the room, this door leads to the bowling lanes. Another cut scene will play. After the scene, head to the end of the fourth lane to find a box of Handgun Bullets. You can talk to Eddie again for another short scene.
Exit out of the Bowl-O-Rama. A short scene will play with Maria telling you to find Laura. Run around the East side of the building to find an alley fence. Go through the fence and head down the alley. The alley ends with a cement wall, but Maria will tell you to go through Heaven’s Night.
Head up the stairs and into the bar. Inside will be a First-Aid Kit on a chair. Exit out through the other end to wind up on Carroll Street.