Welcome to LQ.
Wine has bits of windows - the needed bits, not the flossy bits. In a termional, first run winecfg if you haven't already and configure things. Then cd to the program you want to run and type
wine garmin-plugin.exe
If it's one of those stupid windows filenames,linux is case sensitive and you have to 'escape'(\) special characters like spaces. It might be
wine Garmin\ Plugin.exe
program files becomes Program\ Files
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