I was long drawn more to Melville than Emerson or Thoreau. I landed pretty squarely in the anti-transcendentalist camp by high school, more or less. My affection for the music of Charles Ives withstanding, it's difficult not to see the sentiments of the American transcendentalists as more juvenile than genius.
So with that out of the way ... :
Perhaps the strangest, saddest thing about “Walden” is that it is a book about how to live that says next to nothing about how to live with other people. Socrates, too, examined his life—in the middle of the agora. Montaigne obsessed over himself down to the corns on his toes, but he did so with camaraderie and mirth. Whitman, Thoreau’s contemporary and fellow-transcendentalist, joined him in singing a song of himself, striving to be untamed, encouraging us to resist much and obey little. But he was generous (“Give alms to everyone that asks”), empathetic (“Whoever degrades another degrades me”), and comfortable with multitudes, his and otherwise. He would have responded to a shipwreck as he did to the Civil War, tending the wounded and sitting with the grieving and the dying.
Granted, it is sometimes difficult to deal with society. Few things will thwart your plans to live deliberately faster than those messy, confounding surprises known as other people. Likewise, few things will thwart your absolute autonomy faster than governance, and not only when the government is unjust; every law is a parameter, a constraint on what we might otherwise do. Teen-agers, too, strain and squirm against any checks on their liberty. But the mature position, and the one at the heart of the American democracy, seeks a balance between the individual and the society. Thoreau lived out that complicated balance; the pity is that he forsook it, together with all fellow-feeling, in “Walden.” And yet we made a classic of the book, and a moral paragon of its author—a man whose deepest desire and signature act was to turn his back on the rest of us.