Hi Biking in Bend, looks like you are a new mapper. Welcome! One thing to note is on OSM we don't remove trails that exist, even if they are private, we use the tagging system instead. In this case it might be "access"="private".

Its clear from aerial imagery, strava heatmap data, and street level pictures, these trails running though the field do exist.  

Please read:
osm.wiki/wiki/Why_we_won%27t_delete_roads_on_private_property
https://wiki.openstreetmap.org/wiki/Ground_truth

Let me know if you need help restoring the trails and tagging them appropriately! 