Gentle Annie may refer to:

"Gentle Annie" (song), an 1856 American song composed by Stephen Foster "Gentle Annie" (Tommy Makem song), a song by Tommy Makem Gentle Annie (film), a 1944 American film Gentle Annie, a 1942 novel by MacKinlay Kantor; basis for the film "Gentle Annie", a Celtic mythological figure with similarities to the Irish goddess Anu Cenchrus longispinus or Gentle Annie, a species of grass Gentle Annie Summit, an elevation near Tiniroto, New Zealand Gentle Annie Tramway, a narrow gauge railway near Gisborne, New Zealand

People Francis Joseph Bayldon (1872–1948), Australian master mariner and nautical instructor Anna Etheridge (1839–1913), Union nurse during the American Civil War Alfred Jefferis Turner (1861–1947), Australian pediatrician and entomologist