Network operators work constantly to maintain an appropriate level of reliability in their power supply and to preserve the integrity of the vegetation growing underneath overhead power distribution systems. Accordingly, this article proposes and adopts different approaches to optimally manage vegetation maintenance in such field. Mathematical modeling is used to represent the problem in terms of several aspects involved in vegetation management, based on the technical capacity of the utility company and the reliability goals established by governmental regulatory entities. The solution is a vegetation maintenance schedule in terms of when, where, and which crews must perform the pruning activities along the distribution network. As a result, the Non-Served Energy Level NSEL is minimized and the financial resources earmarked for this type of maintenance tasks are optimized.