1. This solution requires two connections and disconnections to the same pole.

You want to go from the bottom to the top.
You may start at the bottom at any angle.
You don't need more poles. Note that this entails disconnecting and reconnecting to the same pole at different times.

2. Here is the basic solution.

The tricky part is near the X labeled "4".

Credit for these solutions goes to TJ Takei.