Need a new headset?
 

My headset had been creaking for a while until I cleaned and greased it a few weeks ago, and it was completely silent until yesterday, when it started again. Should I just keep cleaning and lubricating it or should I get a new headset with cartridge bearings? I currently have the stock 26 year old headset on the bike.

When You say you lubricated, did you remove the cups from the frame and grease the inside of the frame too?

If not, the re-tightening the bearings after lubricating them might have stopped the creaking temporally.

No, I didn't. How do you get the cups detached from the frame?

I would replace bearings. It will cost about $10. I had a bike from 1989 until recently and the original headset was fine after I replaced the bearings. Loose or cage bearings will flatten and become not round over time. You probably need a shop to remove the cups and at that point might as well replace the headset

Could replace the whole headset for $10 - $20 on the low end.