New Site Help Needed

This is my first site and I need help and direction. I am building a mt biking site:
http://mtbikertrails.com/

I need help with identifying the right plugins for each page and installing them correctly so the format is laid out correctly.

The first page I would like to work on is:
http://mtbikertrails.com/trails/

This is the page that I would like to have a list of locations. The list would start with state and then drill down.

Example: State – CA, Southern CA, Los Angeles
http://www.singletracks.com/california-bike-trails_5.html

It would be cool to drill down on a map and see all of the riding locations.

Step two will be for users to upload the trail they have ridden into a google map and provide some details around it such as on:
http://www.singletracks.com/bike-trails/007.html

I would also like to have users comment on the trails once it is uploaded. I would also like to have a google map display the trail that the user has uploaded.

Let me know what I should do.