New to me 2012 Heritage with 103 cu in. Stage 1, FP3, Cobra Speedster Slashdowns, K&N intake. It is about 85F and sunny today just trying to be sure my bike is ready for a cross country trip. Just got thermometer dipstick and ran to 245F. Seems high to me but I don't have a clue.
Do I need to try and cool it down and if so how?

 

Your ride is already toast.

 

Do yourself a favor . Pull the oil temp dip stick . Wipe it off and throw it as far as you can.
Oil temp is not an issue never has been. It is head temps and the two have nothing in common. The oil flow to the heads lubes , there is not enough oil flow in volume to do much cooling. Want to cool the thing down put good cooling fan or fans on heads.
Get a tune like a Power Vision that will let you check real head temps 270--360 is not uncommon.

 

boro surely you jest

 

Just 245? LOL like smitty said, throw the temp dipstick away and enjoy your ride.

 

Here are some number for you to look at . Real world no tricks just a 103 sitting on a 70 degree day. It show true head temps. The bike had a factory oil cooler standard on it.
Oil temps not dealt with because they don't madder. The heat generated in the heads really heats up the oil. But the oil does not carry enough of the heat away to make any difference.
I know it sounds like a good idea cool the oil bike is cooler but real world not enough cooling and oil flow. That you can not change.

Out side air was about 70 degrees
103 with lowers open
SYN 20/50 oil
Temp management off
No natural air flow
Started bike allowed to idle
At 261 turned on Fan
40 seconds dropped to 255
90seconds 239
120 seconds 225
at this point the drop slowed a bit
3 minutes 219
5 minutes holding 219 @ same 1000 rpms
7 minutes raised to 221
10 minutes 221 1000 rpms holding
Fan off
10 seconds 230
1 minute 248 climbing steady
1 minute 30 262
2 minutes 266
3 minutes 277
3minutes 20 280
4 minutes 293
FAN on drops of 1 degree per second or so
2 minutes 260
3 minutes 248
4 minutes slowed to 237
FAN off allowed to come to 331
Fan on
Fast drop
1 minute 289
came back down to 228