Is there a simple way to know when a crew can clean a ditch on private property that is fed by a road crossing pipe?  

Figure 1. A ditch needing
cleaning off the ROW

 

While the law can be nebulous on the subject, a good general rule of thumb would be to do the following:

Overall, if you are not sure and concerned about increased liability, contact your municipal attorney for guidance.

Resources

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This work by the Cornell Local Roads Program (CLRP) is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 3.0 Unported License.