1654 Queen Christina of Sweden (often considered bisexual) abdicated the thrown, dressed in men's clothing and renamed herself Count Dohna.
1676 MTF transsexual Abbe Francois Timoleon de Choisy attended Papal inaugural ball in female dress. His memoirs, published postmortem, offer the first written testimony of cross-dressing.
1700s "Molly houses" provided a space for the English gay community to meet, carouse and relate to one another. "Mollies" were men who often crossdressed and developed their own queer culture.
1728 Chevalier D'Eon, born Charles d'Eon, was a famous French spy/ambassador who was born male but lived a significant part of his/her life as a woman. Chevalier's birth sex was a hotly debated question.
1804 George Sand, born Amandine-Aurore-Lucile Dupin, became an accomplished French romantic writer as famous for her affairs as for her words. She was the first woman in modern European history to frequently wear men's clothes, shocking her contemporaries.
1839-1844 "Rebecca and her daughters," a group of male-to-female cross-dressers, battled throughout the Welsh countryside destroying road toll barriers, which were making the poor even poorer. These warriors also adopted the names and identities of women.
1850 Crow nation "woman chief" Barcheeampe was spotted by appalled white travelers in Wyoming and Montana; she was renown for her war exploits and for having several wives.
1861 Franklin Thompson, born Sarah Emma Edmonds, fought for the Union Army in the Civil War. During the war, Franklin served as a spy, nurse, dispatch carrier and later was the only woman mustered into the Grand Army of the Republic.
1886 We'Wha, an accomplished Zuni Weaver and potter, was two spirit - born male but lived as a woman. She spent six months in Washington, DC, and met President Grover Cleveland, who never realized this six-foot Zuni maiden was born male.
1897 Dr. Magnus Hirschfeld founded the first gay liberation organization in Germany (the Scientific Humanitarian Committee). Hirschfeld coined the term transvestite and was known to cross-dress himself.
1952 Christine Jorgensen is the first American whose sex reassignment surgery became public. Her surgery caused an international sensation, and for many, she was the first visible transsexual in the media.
1969 Transgender and gender-noncomforming people are among those who resisted arrest in a routine bar raid on the Stonewall Inn in New York City's Greenwich Village, thus helping to ignite the modern LGBT rights movement.
1974 Jan Morris, one of Britain's top journalists who covered wars and rebellions around the globe and even climbed Mount Everest, published Conundrum, a personal account of her transition. The book is now considered a classic.
1989 Celebrated jazz musician Billy Tipton died in Spokane, Washington, revealing that he was a woman. Tipton, who played in big bands in the 40s and 50s, lived for 56 years as a man, marrying several times and raising children.
1991 FTM activist Jamison "James" Green took over Lou Sullivan's FTM newsletter and transformed it into FTM International, Inc., the world's largest information and networking group for female-to-male transgender people and transsexual men.
1993 Cheryl Chase founded the Intersex Society of North America (ISNA) to build awareness and offer support to intersex people.
1993 Transgender youth Brandon Teena was raped and murdered in Humboldt, Nebraska. This hate crime brought widespread attention to transgender discrimination and violence and became the subject of the award-winning film, Boys Don't Cry.
1997 Trans activist Leslie Feinberg published Transgender Warriors: Making History from Joan of Arc to Dennis Rodman, a who's who of transgender people throughout world history that traces the roots of transgender oppression.
Source - Bending the Mold: An Action Kit for Transgender Youth
Lambda Legal (2004)