The "modern" Harley V-Twin can't be allowed to just sit and idle for extended periods without airflow over the engine. These things aren't made like the engines in stationary equipment (compressors, generators, etc.), and they won't tolerate this kind of activity for long periods of time.
Oil expands as it heats up. I suggest that you never fill to the full mark when cold; in fact I fill to only 1/8" over the add mark when cold which corresponds to about halfway between add and full when hot. These engines do not like excessive oil levels and will often protest by blowing some out of the air cleaner and all over your leg and the side of the bike.
Normal oil temperature is 230°F. If you are seeing 300°F plus on a regular basis, you need to make sure you're using a top quality synthetic and you need to change it more often. You might also want to take a look at your riding habits. For instance, shut the engine down when sitting for more than a minute or two, like for a train.
If you want to reduce the excessive engine temps, get the bike tuned. The stock EPA compliant air/fuel ratio is lean, which results in a hotter burn. While excess fuel will result in higher emissions, it will also result in cooler running.
Jerry