I noticed my only working bike has a noticeable amount of play in the headset tonight.
All the nuts seem tight. Was recently worked on and the steering was very stiff when I got it back, for whatever that's worth.
Safe for short rides around the neighborhood? It's a mid 90s Trek 930 with a threadless steerer.
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Ha, when I read the title I thought you were talking about riding with earbuds...
Not quite awake yet...
In absolute terms or in theory it is not safe. A loose headset could contribute to a loss of control accident. In practice people ride on loose headsets and never know it.
Will everything fly apart and crash you? Almost certainly not. This is simple conservative design that doesn't have that failure mode. Unless something is going on here you didn't see and didn't tell us about.
It suddenly got loose. It won't suddenly get tight and fly into perfect adjustment. Get to your mechanic. Most likely case is a one minute fix. Don't mess with it yourself.
It is most likely an adjustment issue, I doubt it became so loose that the bearings fell out. See if you can tighten the bottom nut by hand. And unless you are traveling at a high rate of speed or downhill I would not worry too much about it. Threaded headsets can come loose often and when it happens on the road you usually can tighten it enough by hand to get you home safe. Your fork and front wheel are not going to come flying off. Have it professionally adjusted soon if you are not comfortable doing it yourself as to not cause any damage to the parts.
Headsets are simple assemblies. Any good mechanic will be able to get it right.
I never meant to be snobbish about my reply, Just start with simple things first.... make sure it is in adjustment and if the shakiness continues then look into alignment issues. I am basing this off of your comment that you recently had the bike serviced, a lot of mechanics will make sure the headset is snug even if you bring your bike in for other issues. Another thing is you said it seemed stiff when you first got it back. The two headset nuts may seem tight together but the whole assembly may be loose.
Don't worry about "any of the above". Sheldon is just covering all the bases. Any mechanic knows all that without thinking. The only likely way this is more serious than just snugging down both nuts again is if there's a problem with a bent steerer. If you've never crashed the bike that's not a problem either. And every mechanic is going to check for that in seconds while he gets on with the job. If you ride/have ridden too long with a loose headset the threads will get sloppy and won't stay put without a locking nut or loctite or whatever. Ride with it loose for a l-o-n-g time and you could ovalize the headtube. If it's not just plain flapping in the breeze loose and you attend to it soon you should be fine.
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