She attended the State Normal School in Albany and in 1883, proceeded to Vassar College, where she earned her AB degree. Like her siblings, Sherwood originally pursued a career in education, teaching chemistry, however, she shifted her interest to medicine. She attended the University of Zurich, and in 1890, obtained her medical degree. A year later, she applied but was turned down, from the College of Physicians and Surgeons in New York City. Equipped with recommendation letters from a prominent medical practitioner and educator she studied under at Zurich, she applied to Johns Hopkins Hospital and was offered a spot in Dr. William H. Welch's laboratory, and in Dr. William Osler and Dr. Howard Kelly’s hospital wards. She was not able to hold her residency there, and a few years later, in 1892, she opened her own practice with her close friend Lilian Welsh. The medical practice did not flourish, but the pair decided to stay in Baltimore anyway and eventually took over the Evening Dispensary for Working Women and Children. During this time, they were in close vicinity to Johns Hopkins Hospital, and had many opportunities to interact, learn, and connect with other doctors, attend lectures, and join groups and organizations. This helped recognize her interest was leading towards preventive medicine, women’s health, and childcare.
Later life
In 1894 Sherwood was appointed as medical director of the girl's preparatory school in Baltimore, the Bryn Mawr School, she also gave lectures on pathology at the Woman’s Medical College in Pennsylvania and traveled to the Bryn Mawr College to give lectures on hygiene and college physician work. Her life was dedicated to the education and health of women and she served many different public health movements and organizations in her time. While employed at the school, she was chosen to help develop and direct, the Bureau of Child Welfare in the city health department in Baltimore, serving as its head until 1924. She was also the first chairman of the obstetrics section in the National Association for the Prevention of Infant Mortality and worked on the Maryland Tuberculosis Commission. Working at the dispensary gave her an introduction and vast knowledge and experience with childbirth and the care of children. She was appointed the chairman of the midwifery committee of the Medical and Chirurgical Faculty part of the Maryland State Medical Society, as well as served membership on the Executive Committee of the Baltimore Babies’ Milk Fund Association. Sherwood also played a role in women’s clubs in Baltimore. She was a member of the Baltimore Association for the Promotion of the University Education of Women, advocated for suffrage and was Susan B. Anthony's physician, was a charter member and one of the original board managers of the Arundell Club along with Welsh, as well as the Arundell Good Government Club. During all of her involvements, she served the Bryn Mawr School and held her connections and friendships with Welsh and a few other women doctors.
