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I work for a state government's fisheries service, and lately we've been digitizing a lot of our regulatory boundaries within the state's waters that we'd like to service out on web maps. Unfortunately since a lot of these boundaries are in a bay and follow the shoreline, the polygons contain a lot of vertices which greatly inflates the file size of the shapefiles.

I know I can use the generalize tool to simplify the polygons, but as these polygons represent legal boundaries, we need to maintain their accuracy as much as possible. Are there any other tricks I could use to reduce the file size without risking spatial accuracy?

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I would try file gdb. you can set compression. and the move to web is easily maintained. – Brad Nesom Feb 5 at 16:36

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Try reducing the lengths of attribute fields, if your data allows for this. DBF will "pad" character fields out to the full width of the field, which in some cases makes the DBF much larger than it needs to be.

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