Join Date: Dec 2007
Location: Austin, Texas, USA
Bikes: Trek 520, Lightfoot Ranger, Trek 4500
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Yes, I've broken both front and rear racks - though on fairly rough roads.
I haven't broken the mounting bolts in the rear, though early on I learned to keep checking bolts for tightness since I had one occasion where a bolt slowly worked loose and then fell out. If you are going for extended time, it also helps to have an extra bolt of key components.
I had a rear blackburn rack and a front surly rack when I cycled across Russia. There was ~1700km of gravel road that was more obnoxious than gravel roads I've traveled in North America. I was carrying a reasonably heavy load in my panniers. What failed on the rear rack was the metal strap that connected the rear rack to seat stay. Only one of two straps failed and I was able to duct tape it to keep it going.
What failed more than once on the front rack was the metal bracket in fashion similar to what happened to Herman Veldhuizen on his ride: http://www.hermanveldhuizen.com/wp/?cat=28
In these failures I believe it was a combination of weight and extended touring over rough roads. Even some of the paved/concrete roads further west in Russia were occasionally quite rough. I had some touring miles ridden before then including two trips across the US, one across Canada and one lap around Australia without problems.