Set in the 1600s at Plymouth Plantation, this installment of the Obadiah series is a retelling of the Tortoise and the Hair. Obadiah is sure that he is much faster than his younger sister Rachel, and that he can beat her anytime. When they have the opportunity to run a message about the landing of the Speedwell, Obadiah challenges Rachel to a race. Convinced he'll win, Obadiah lets Rachel get a head start, and stops to pick blackberries. Not discouraged by her brother's bragging, Rachel runs on, and arrives well before Obadiah. Rachel is given two silver coins as a reward, and Obadiah learns a lesson in humility.
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