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Handlebar shimmy

Yes, the steering head bolt needs to be adjusted. Worth taking it to the shop for this. Takes about 20min for them to do it.
 
A shimmy in the front end could be caused by a few different things. The steering head is one of them and tire balancing/damage or front end not up to the torque specs is another.

You can do the front end steering head yourself if you have the manual, it's not difficult.

This will give you some input on it if you check the fall away and find it excessive...

Softail Clunking Front End - Archive - Harley Davidson Community
 
I have work on a few bikes that the complaint was a shimmy around 40mph. One was a 2003 Super Glide. The problem was the spokes in the rear wheel were not tight. If you have a spoke wheel it is a good idea to check them every now and then. An Old Norton mechanic once told me " if it shakes in the front look at the rear".
 
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