create custom .poly file for OpenStreetMap

buffer county polygon.shp by 5 miles in QuantumGIS(QGIS).

convert to line.

convert to .gpx from .shp with ogr2ogr.

upload to http://www.geocaching-dresden.de/tools/gpx-to-poly/

UPDATE: found this http://www.openstreetmap.info/examples/polygon.html

FINAL WORKFLOW:

County.shp > buffer 5 mi, generalize, polygon-to-line (if needed) > ogr2osm > JOSM, Save/Save-As (reformats xml I’m guessing) > osm2poly.pl usage: osm2poly.pl orange_b.osm > orange_b.poly