Craig Bolton writes with these additional recommendations:
Bob’s recommendations are great. But here are several more [with my evaluation of the “level” you should be at before you tackle them and how centrally or tangentially important they are in developing an accurate understanding of libertarianism].
At some point, if you haven’t done so long ago, you should read some of the principal “classics,” such as:
John Locke, Second Treatise On Government [elementary and essential]
Baruch Spinoza, Theological-Political Treatise and Political Treatise [intermediate and recommended]
Thomas Paine, Common Sense and The Rights of Man [elementary and essential]
Adam Smith, An Inquiry Into The Nature And Causes Of The Wealth of Nations [advanced and requires a prior knowledge of Smith’s terminology; absolutely essential at some point]
Herbert Spencer, The Man Vs. The State [elementary and recommended]
Then you might try:
(1) Bernard Bailyn, The Ideological Origins of the American Revolution. [Intermediate and recommended]
(2) Jim Powell, The Triumph of Liberty [Elementary and essential]
(3) Frederic Bastiat, Economic Sophisisms and Selected Essays On Political Economy [two different books] [Elementary and essential]
(4) William O. Reichert, Partisans of Freedom [advanced but marginal]
(5) Pierre J. Proudhon, The General Idea of the Revolution In the 19th Century [Proudhon was certifiable, but a very interesting writer] [intermediate and marginal]
(7) Jeffrey R. Hummel, Emancipating Slaves, Enslaving Free Men [Intermediate and highly recommended]
(8) Ludwig von Mises, Liberalism [Elementary and essential]
(9) Ludwig von Mises, Socialism [Intermediate and essential]
(10) F.A. Hayek The Road To Serfdom [new critical edition edited by Bruce Caldwell] and Individualism And Economic Order. [Intermediate and important]
(11) F.A. Hayek, Individualism and Economic Order [Intermediate to Advanced and essential]