Trams connect MOST hotels. Usually the hotels that are owned by the same people are connected, but not always. You can probably get from one end of the strip to the other without spending a lot of time outside, it's just a matter of how LONG you want it to take. Trams are an easy way to get from hotel to hotel, but definately not QUICK. You usually have to go through the entire casino to get to the next tram station.
And in October, the weather should be GREAT here.