After his older brother was killed in the American Civil War, the family traveled to Europe, visiting England, Switzerland, and France, during which Wolcott continued his studies.

He then attended Harvard Law School, graduating in 1874, and was admitted to the Suffolk County bar the same year.

He became increasingly involved in the affairs of his father's business associates, eventually being appointed to serve on a number of corporate boards.

He was also involved in philanthropic organizations, serving as a member of the Boston Provident Association, and as trustee of the Eye and Ear Infirmary and the Massachusetts General Hospital.

Wolcott became involved in politics not long after opening his law practice, winning a seat on the Boston Common Council in 1877 which he held for three years.

Wolcott began to assume a more prominent role in Republican circles after his father's death.

He was a founding member and the first president of the Young Republican Club, an organization designed to inject new life into the party.

He was offered a variety of diplomatic posts by President William McKinley, but refused them, and embarked on a trip to Europe with his family in May 1900.