Weld joined Our America Initiative's 2016 Liberty Tour a number of times, speaking alongside other libertarian leaders and activists such as Law Enforcement Against Prohibition executive director and former Baltimore Police Chief Neill Franklin, Free the People's Matt Kibbe, Republican activists Ed Lopez and Liz Mair, Conscious Capitalism's Alex McCobin, Reason Foundation's David Nott, Foundation for Economic Education's Jeffrey Tucker, the Libertarian Party's Carla Howell, and author and journalist Naomi Wolf; the tour raised "awareness about third party inclusion in national presidential debates" and "spread the message of liberty and libertarian thought."