The trick is to add the following lines to settings.mos in c:/Users/USERNAME/AppData/Roaming/Dynasim:
Utilities.setenv("MODELICAPATH", "C:\Users\USERNAME\Documents\Dymola");
openModel("c:\Users\USERNAME\Documents\Dymola\UserDefined\package.mo")
The first line adds the directory to the path that Dymola uses to search for packages that have not been loaded prior to the first run of a model, and the second line loads the specified package. These two commands may be somewhat redundant, but I am doing both because I want to make sure my custom packages are on the path in addition to loading the UserDefined package.