So I just started a new character, and after killing the dragon I started off to windhelm to join the stormcloacks to my surprise I come across a run down wagon and as luck would have it I find Cicero asking for my help to convince the farmer to fix his wagon. My question is has anyone else seen this before?

Yeah. I helped him. It's actually really near winterhold so it's findable. You get a neat little dialogue option later

I saw it today. Poor Cicero is stuck, and if you don't convince the farmer to help him,

Seriously.

Mine was near whiterun.

It's kind of http://www.uesp.net/maps/srmap/srmap.shtml?centeron=Loreius+Farm. I came across it while traveling to Korvanjund from Whiterun.

Finally ran into him the other day, so yeah. Dear god his voice grates on my nerves. After convincing the farmer to help him I took Cicero's gold, stole his horse and ran.

Yes, it's a quest:

As much as you might want to call a guard over to arrest this stange jester, it might be in the best interest of the farmer and his wife to convince the farmer to assist Cicero and fix the wagon wheel.