I had a 2003 Ultra with an oil dipstick thermometer. On a hot day during a long ride the oil temp would be about 230.

I now have a 2009 Ultra with an oil dipstick thermometer. On a hot day during a long ride the oil temp can be as high as 265.

I realize that the 2009 has a leaner mix. My 2009 is 100% stock.

Am I damaging the engine at 265 degrees? What is the maximum safe oil temp. How can I get the bike to run cooler.

 

I'd like to know the answer to your question. I to have the same temp. reading on my dipstick, sometimes higher.

 

You're not damaging your engine with the oil at 265F but it's a little high, especially if it's during a ride at highway speed.
Are you sure your dipstick is accurate? Best way to know is to dip it in boiling water. It should read 212F (at sea level).
If it is accurate, there are several solutions to lower engine temp, the most obvious is to run richer. Like you said, stock bikes are set-up very lean at the factory in order to comply with EPA regulations.
You can achieve it by installing a tuner like a SEST, PCV or TTS and increase the % of fuel in the air/fuel mixture.
Or you might want to look at XIEDs if you're running stock AC, ECM and pipes.
In addition, you can also install an oil cooler and use good synthetic oil instead of dino. Good synthetic oils like Mobil1, Redline or Amsoil tolerate temperatures close to 400F before breaking down.

All this will lower the engine temperature but I had to go 1 step further to eliminate the problem on my 09 Ultra. I ditched my stock headers and installed true duals (2-2). My passenger hasn't complained about excessive heat since I did it although we rode in high temp this past week.

 

UncleBob,

Get an oil cooler. For $250-300 bucks you'll cool your oil a good 20 degrees. I ride in the California desert quite a bit and often saw the same temps you're seeing before I got the HD cooler. Now on those 100*+ days I'm rarely above 230.

Welcome to the money pit!

 

I had the HD oil cooler on my 2003. It was poorly designed and leaked around the hose fittings. One hose was routed under the frame and it got split by a rock tossed up by the front tire. It's not much fun breaking down on I80 ten miles out of Winnamucca NV in August. By the way, I do run Amsoil and still get high temps.

 

That's the purpose of the oil temp gauge, to worry the crap out of you. Harley has been building these air cooled engines for a long time and they've got it pretty well figured out by now.

 

The quickest and cheapest way to lower the oil temp on an Ultra is to remove the lowers. Five minutes and free.

Bwana

 

I almost bought one of those oil temp dipsticks, until the dealer talked me out of it. He said all it does is freak you out, he wanted to stop selling them all together.

 

Forgive me but what do you mean with "remove the lowers"? I'm not familiar with this term. Please, could you explain? Thanks.

 

Lower fairings. That are in front of your lower leg.