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Leo travels to Massachusetts Bay Colony and meets Anne Hutchinson, a few days before her 1637 trial and conviction. Afterwards, he runs into John Winthrop, one of the founders of this colony.
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Leo meets Thomas Paine, the author of Common Sense. This pamplet inspired colonists to declare and fight for their independance from Britain.
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Leo meets Deborah Sampson, a woman who had disguised herself as a man in order to fight at the battles of the American Revolution.
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Leo listens to Horace Mann give his speech on educational reform.
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Leo travels to the Underground Railroad. He helps Harriet Tubman assists runaways on their journey to Canada.
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Leo travels to a Civil War battle with General Ulysses S. Grant and also meets Clara Barton, who had been nursing injured soldiers throughout the war.