I think "A Week on the Concord and Merrimack Rivers" is both charming and funny. The book is a view into the very early industrialization of the United States, as framed by two brothers taking a boat trip. I also recommend "Civil Disobedience", an essay which proposes a program of peaceful, active resistance to unjust government. This essay inspired both Gandhi and Martin Luther King, Jr. Choice quotes:

> I ask for, not at once no government, but at once a better government.

> There are thousands who are in opinion opposed to slavery and to the war, who yet in effect do nothing to put an end to them; who, esteeming themselves children of Washington and Franklin, sit down with their hands in their pockets, and say that they know not what to do, and do nothing; who even postpone the question of freedom to the question of free trade, and quietly read the prices-current along with the latest advices from Mexico, after dinner, and, it may be, fall asleep over them both. What is the price-current of an honest man and patriot today?

Walden is often recommended but can seem a little out of context in a world that has industrialized and tends toward bowling alone. Even so, it's worth understanding Walden for the perspective Thoreau puts forward concerning the usefulness of inventions and their reflection on and in communities.

> As with our colleges, so with a hundred "modern improvements"; there is an illusion about them; there is not always a positive advance. The devil goes on exacting compound interest to the last for his early share and numerous succeeding investments in them. Our inventions are wont to be pretty toys, which distract our attention from serious things. They are but improved means to an unimproved end, an end which it was already but too easy to arrive at; as railroads lead to Boston or New York. We are in great haste to construct a magnetic telegraph from Maine to Texas; but Maine and Texas, it may be, have nothing important to communicate. Either is in such a predicament as the man who was earnest to be introduced to a distinguished deaf woman, but when he was presented, and one end of her ear trumpet was put into his hand, had nothing to say. As if the main object were to talk fast and not to talk sensibly. We are eager to tunnel under the Atlantic and bring the Old World some weeks nearer to the New; but perchance the first news that will leak through into the broad, flapping American ear will be that the Princess Adelaide has the whooping cough. After all, the man whose horse trots a mile in a minute does not carry the most important messages; he is not an evangelist, nor does he come round eating locusts and wild honey.

A much shorter read in the same vein–and without all the digressions about the economics of farming beans–is "Life Without Principle". I recommend reading that first over Walden as something of a primer. By the time of Life Without Principle Thoreau was giving public lectures and had gotten better at shorter arguments (though he likely felt that to-the-point declarations were not the path to wisdom but that a round-about argument which required quiet contemplation while walking was).

> Do we call this the land of the free? What is it to be free from King George and continue the slaves of King Prejudice? What is it to be born free and not to live free? What is the value of any political freedom, but as a means to moral freedom? Is it a freedom to be slaves, or a freedom to be free, of which we boast? We are a nation of politicians, concerned about the outmost defences only of freedom. It is our children's children who may perchance be really free. We tax ourselves unjustly. There is a part of us which is not represented. It is taxation without representation. We quarter troops, we quarter fools and cattle of all sorts upon ourselves. We quarter our gross bodies on our poor souls, till the former eat up all the latter's substance.

Thoreau was eccentric but purposefully. He's one of America's great philosophers and well worth reading.