November 7 – José Sarria, the first known openly gay candidate for political office in the world, shocks political observers by garnering nearly 6,000 votes in his bid for a seat on the San Francisco Board of Supervisors. This feat marked the beginning of the notion that gays could represent a powerful voting bloc.
February – The Black Cat Bar, having struggled for several months to survive without liquor sales, closes permanently.
September 19 – A small group pickets the Whitehall Street Induction Center in New York City after the confidentiality of gay men's draft records was violated. This action has been identified as the first gay rights demonstration in the United States.
December 2 – Four gay men and lesbians picket a New York City lecture by a psychoanalyst espousing the model of homosexuality as a mental illness. The demonstrators are given ten minutes to make a rebuttal.
April 25 – An estimated 150 people participate in a sit-in when the manager of Dewey's restaurant in Philadelphia, Pennsylvania refused service to several people he thought looked gay. Four people are arrested, including homophile rights leader Clark Polak of Philadelphia's Janus Society. All four are convicted of disorderly conduct. Members of the society also leaflet outside the restaurant the following week and negotiate with the owners to bring an end to the denial of service.
May 29 – Ten men and three women participate in an ECHO picket of the White House.
October 23 – Thirty-five ECHO demonstrators picket the White House. The last White House picket; demonstrators felt, with this event, that picketing the White House had lost its effectiveness as a tactic.
January – The South African Police raid a gay party attended by about 300 people in Forest Town, a suburb of Johannesburg. This attracts much public and political attention, leading in 1969 to an extension of the criminalization of male homosexuality.
January 21 – Time magazine publishes an unsigned two-page article, "The Homosexual in America". The article includes statements such as "Homosexuality is a pathetic little second-rate substitute for reality, a pitiable flight from life. . . . it deserves no encouragement . . . no pretense that it is anything but a pernicious sickness."
April 21 – Activists stage a "Sip-In" at Julius, a bar in New York City, challenging a state Liquor Authority regulation prohibiting serving alcohol to homosexuals on the basis that they are disorderly. Although the resultant complaint to the Liquor Authority results in no action, the city's human rights commission declares that such discrimination could not continue.
May 21 – A coalition of homophile organizations across the country organizes simultaneous demonstrations for Armed Forces Day. The Los Angeles group holds a 15-car motorcade (which has been identified as the nation's first gay pride parade) and activists hold pickets in the other cities.
July 18 – Around 25 people picket Compton's Cafeteria in San Francisco when new management begins using Pinkerton agents and police to harass gay and transgender customers.
August – Gay and transgender customers riot at Compton's in response to continued police harassment. The restaurant and the surrounding neighborhood sustain heavy damage. The following night demonstrators throw up another picket line, which quickly descends into new violence and damage to the restaurant.
September – The Chicago chapter of the Mattachine Society pickets the Chicago Tribune and the Chicago Sun-Times for routinely ignoring press material and refusing advertising from the organization.
The book Homosexual Behavior Among Males: A Cross-Cultural and Cross-Species Investigation by Wainwright Churchill III breaks ground as a scientific study approaching homosexuality as a fact of life rather than as a sin, crime or disease, and introduces the term "homoerotophobia", a possible precursor to "homophobia".
Pierre Trudeau, then Canada's Minister of Justice, introduces an Omnibus Bill to overhaul Canada's criminal laws, which includes decriminalizing homosexual acts. Trudeau tells reporters, "There's no place for the state in the bedrooms of the nation" and "What’s done in private between two consenting adults doesn’t concern the Criminal Code." After 18 months of debate, the bill becomes law in 1969.
January 16 – The Louisiana Supreme Court rules that the state's statutory ban on "unnatural carnal copulation" applies to women engaged in oral sex with other women.
February 11 – In a follow-up action to the Black Cat demonstration, around 40 picketers demonstrate in front of the Black Cat in coordination with hippies and other counterculture groups who had been targeted by police for harassment and violence.
March 7 – CBS airs "The Homosexuals", an episode of CBS Reports. This first-ever national television broadcast on the subject of homosexuality has been described as "the single most destructive hour of antigay propaganda in our nation's history."
April 23 – The Student Homophile League of Columbia University pickets and disrupts a panel of psychiatrists discussing homosexuality.
August – Following the arrest of two patrons at the Los Angeles gay bar The Patch, owner Lee Glaze organizes the other patrons to move on the police station. After buying out a nearby flower shop, the demonstrators caravan to the station, festoon it with the flowers and bail out the arrested men.
April – When gay activist and journalist Gale Whittington is fired by the States Steamship Company after coming out in print, a small group of activists operating under the name "Committee for Homosexual Freedom" (CHF) pickets the company's San Francisco offices every workday between noon and 1:00 for several weeks.
May 21 – The Committee for Homosexual Freedom pickets a Tower Records store for several weeks following the firing of an employee believed to be gay. The employee is re-hired.
May 21 – In South Africa, the Immorality Amendment Act, 1969 introduces Section 20A, the infamous "men at a party" clause, which criminalised all sexual acts committed between men "at a party", where "party" is defined as any occasion where more than two people are present. The amendment also raised the age of consent for male homosexual activity from 16 to 19, although "sodomy" and "unnatural acts" were already criminal.
July 24 – The Gay Liberation Front, a radical leftist group addressing not only gay rights but other left-wing causes, forms in New York City. Over the next few years dozens of local GLF chapters would form across the country.
August – Canada decriminalizes consensual sex between adults.
October 31 – Time magazine runs a cover story entitled, "The Homosexual: Newly Visible, Newly Understood". The author, Christopher Cory, presented a "case for greater tolerance of homosexuals" yet "emphasized the effeminate side of homosexuality to the exclusion of everyone else," resulting in a protest at the Time-Life Building on November 12, 1969.
December 28 – The Los Angeles chapter of Gay Liberation Front announces plans to establish Stonewall Nation, the world's first legally recognized gay village, by moving several hundred gay people to Alpine County, California, recalling the county government and electing an all-gay slate. After a brief flurry of national attention, GLF announces that the plan is off.
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