He attended Roxbury Latin School and then Harvard Medical School, where he obtained his M.D. in 1857 at the age of 20.
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After a larger student threw his books downstairs and refused to apologize, Windship determined to build himself up by practicing gymnastics at the school gym, working on the various equipment, including the spring-board, horse, vaulting apparatus, parallel bars, suspended rings, horizontal and inclined ladders, pulley-weights, pegs, climbing rope, and trapezoid every evening after classes.
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