This is what I have done. Not sure if it is the best way, but it works well.
desc "Sync the uploads to the new current project" task :sync_uploads, :roles => [:app] do run "mkdir -p #{shared_path}/uploads" run "chown #{user}:#{user} #{shared_path}/uploads/" run "ln -nsf #{shared_path}/uploads #{current_path}/public/uploads" end
I just make sure the uploads are saved in system/uploads/ (the system folder symbolic link is made my capistrano). That way I don't have to worry about putting it in my deploy.rb file.