He relocated to New York in 1856 and became the assistant editor of literary and social commentary weekly for The Saturday Press, in print intermittently from 1858 to 1866.

[3] Winter became a regular at the center of Greenwich Village's Bohemian hotspot, Pfaff's, among writers and artists, such as Walt Whitman, Mark Twain, Winslow Homer, Edwin Booth, Adah Isaacs Menken, Ada Clare, and Horatio Alger Jr.

In 1860, Winter married Scottish poet and novelist Elizabeth Campbell, raising their five children in Staten Island, New York.In the 1880s, he began publishing biographies of thespians like the Jefferson family and Edwin Booth.

His 1912 book The Wallet of Time offers a retrospective look at the development of nineteenth-century theater; in the preface, he states that "[a] ruling purpose of my criticism has been... to oppose, denounce, and endeavor to defeat the policy which, in unscrupulous greed of gain, allows the Theatre to become an instrument to vitiate public taste and corrupt public morals" (xxiv).

Winter left two archives of biographies and essays on stars like Edwin Booth and Sir Henry Irving, in addition to career papers documenting his work as a writer and critic.