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I'm trying to create a very simple polygon shapefile of some new areas defined by boundaries specified by my company.

These boundaries don't match any known shapefile as it's a mapping of their infrastructure. They've given me a hardcopy scan of the boundaries traced over a google map.

What I need to do is create a simple shapefile from this, bring into R and match coordinates of another dataset to each specific polygon so I can run some analysis in R based per region.

What would be the quickest and easiest way to do this?

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Google Earth will allow you to export drawn shapes to KML or KMZ. You can give each feature some limited attribution. You can also convert it to a shapefile later.

To do this, I would first create a folder in either My Places or Temporary places: Create folder

Then add a polygon to the folder: Add Polygon

Then give it a name, a description and draw! Draw a new shape for each unique feature. Create polygon

When you're done you can right click the whole folder and Save Place As... Save As

And make it a kml. If you don't have access to something like ArcGIS or Global Mapper, or don't feel like getting into QGIS, there are several free converters online that will convert from KML to shapefile.

Here's one: http://www.zonums.com/online/kml2shp.php

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    Damn that was quick! coincidentally after embarrassingly struggle to figure out how to do this, I stumbled upon openlayers for QGIS which is extremely easy to use for my application!. – The Ripper Jul 7 '15 at 18:22

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