Counterculture Reading
Since people have been asking me for suggestions, I have to say,
there aren't any good books that really capture the sixties, in my opinion.
The only media item I would strongly recommend are two movies,
"The Return of the Secaucus Seven", by John Sayles,
and "For Jonah Who Will Be 25 in the Year 2000" (Jonas qui aura 25 ans en l'an 2000),
by Swiss filmmaker Alain Tanner, 1976,
but to explain why these really capture the essence of the sixties would take a book by itself.

But if you didn't live through it, you need <something> to give you some information
about the history of the counterculture, so here are some starting points:

The Best Book About Counterculture History:
A People's History of the United States - Howard Zinn - READ IT ONLINE!
(doesn't cover the sixties, but gives the background of why many things happened)

Books and Movies about Sixties Counterculture (looking back):

Do You Believe in Magic? - Annie Gottlieb, 1987 (if you only read one book, I guess this is the best)
The Making of a Counter Culture - Theodore Roszak, 1969 (too general, but he tries his best to explain) READ IT ONLINE
Communes USA - Richard Fairfield, 1971
Ringolevio: A Life Played for Keeps - Emmett Grogan, 1972( (the Diggers and Hashbury)
The Rolling Stone magazine write-in on the Sixties 1976 - two selections from that issue: 1 2
Apocalypse Now - Francis Ford Coppola 1979 (the Vietnam war)
Parting The Waters: America In The King Years 1954-63 - Taylor Branch 1988 (the civil rights movement)
Return of the Secaucus 7 - John Sayles, 1980
Storming Heaven - Jay Stevens, 1987 (LSD) - READ IT ONLINE
It Was Twenty Years Ago Today - Derek Taylor, 1987 (the music)
The Sixties: Years of Hope, Days of Rage - Todd Gitlin, 1987 (the politics)
Walking on the Edge of the World - George Leonard, 1988 (the human potential movement)
May Fools ( Milou en mai ) - Louis Malle, 1990
The Doors - Oliver Stone, 1991 - the scenes of Venice!
Ok, ok, the movie of Woodstock, if you haven't seen it already, but it was only ONE weekend,
and LOTS else happened besides that one festival, an event which lots of us were NOT at . . .
(Notice that I am NOT including anything by Tom Wolfe or Hunter S. Thompson)

The Group - Mary McCarthy, 1963 (about the 1930s, but also what the fifties was like)
Memoirs of an Ex-Prom Queen - Alix Kates Shulman, 1969 (the fifties and early sixties)
Loose Change: Three Women of the Sixties - Sara Davidson, 1977
The Women's Room - Marilyn French, 1977 (a devastating account of the woman's revolution - skim the middle, be sure to read the end)

Books that influenced Sixties Counterculture:
Thoreau - everything he wrote i.e. Walden, On Wildness etc etc etc
A Sand County Almanac - Aldo Leopold 1949 (the beginnings of the ecology movement)
The Sea Around Us - Rachel Carson 1951 (just hearing about this was enough to start the environmental movement)
Hermann Hesse - everything he wrote! Siddhartha, Steppenwolf etc etc etc
Catcher in the Rye - J. D. Salinger 1951 (the fifties)
The Doors of Perception - Aldous Huxley 1954 (psychedelics as ritual)
To Kill a Mockingbird - Harper Lee 1960 (social justice)
Summerhill: A Radical Approach to Child Rearing - A.S. Neill 1960 (the new child-care)
On Becoming a Person - Carl Rogers 1961 (the new psychology)
Stranger in a Strange Land - Robert Heinlein 1961 (the dream)
Franny and Zooey - J. D. Salinger 1961 (Buddhism) (my all-time favorite book)
R. Buckminster Fuller - everything he did
Gregory Bateson - everything he did / global vision site
The Morning of the Magicians - Louis Pauwels 1963 (magic)
Understanding Media - Marshall McLuhan 1964 (the new media)
Games People Play - Eric Berne1964 (the new psychology)
The Making of a Quagmire - David Halberstam 1964 (the mistake of American involvement in the Vietnam Civil War)
Rod McKuen's books of poems: Stanyan Street and Other Sorrows 1966 (he made San Francisco sound very romantic and a lot of us went to check it out)
Been Down So Long It Looks Like Up to Me - Richard Farina 1966 (the idiocy of life)
Blowup [movie] - Antonioni 1966 (the subjectiveness of reality)
The Whole Earth Catalog - all issues 1968 - 1998
Don't Look Back (movie) 1967 (why everyone felt that Bob Dylan was speaking for them)
Performance (movie - Nicholas Roeg) 1970
Cartoons of Ron Cobb - his books are worth a fortune now
Another Roadside Attraction - Tom Robbins 1971 (a fantasy, but he captured the magic)
At The Edge of History - William Irwin Thompson 1971 (and everything else he wrote)
Be Here Now: Baba Ram Dass, Lama Foundation 1971 (the bible)
The Crack in the Cosmic Egg: Joseph Chilton Pearce 1971 (the joining of science and religion)
Filipino Food - Ed Badajos 1972 (gorgeous mindbending comic, out of print, which is really sad)
Small Is Beautiful (Economics as if People Mattered) - E. F. Schumacher 1973 (the new economics)
Handmade Houses (A Guide to the Woodbutcher's Art) - Boericke & Shapiro 1973 (the architecture)
The Collective Unconscience of Odd Bodkins - Dan O'Neill 1973 (deep mysteries of life)
Hear the Sound of My Feet Walking Drown The Sound of My Voice Talking - Dan O'Neill (also sadly out of print)
Robert Crumb's comics, of course - Keep On Truckin'!
The Coevolution Quarterly which became The Whole Earth Review - all issues 1974-1985

Beat Counterculture:
Jack Kerouac - everything he wrote - Dharma Bums, The Subterraneans, etc etc etc
Go - John Clellon Holmes 1952
The Holy Barbarians - Lawrence Lipton 1959
Genesis Angels: The Saga of Lew Welch & the Beat Generation - Aram Saroyan
Naked Angels: The Lives and Literature of the Beat Generation - John Tytell 1976
Venice West: The Beat Generation in Southern California - John Maynard 1991
Off the Road: My Years With Cassady, Kerouac, and Ginsberg - Carolyn Cassady

Earlier counterculture history:
Bohemia: The Protoculture Then and Now - Richard Miller 1978
The Year of the Wombat: England 1857 - Francis Watson 1974?
Bohemia in London - Arthur Ransome 1984?
Henry Miller - what a sweet guy, underneath it all
Jack London
The Alternative Communal Life in New America - William Hedgepeth 1970

Not about the counterculture, but about the Baby Boom and other generations:
Great Expectations: American and the Baby Boom Generation - Landon Y. Jones

Many more books can be read online at The Radical Reader

More sixties books I've read or looked through:
We Are the People Our Parents Warned Us Against - Nicholas von Hoffman 1968, 1989
The Youth Communes - Roy Ald 1970
The Greening of America - Charles Reich 1970

The Children of Prosperity: Thirteen Modern American Communes - Hugh Gardener 1978 (St. Martin's Press ) CQ Fall 1981 p. 89
The Nine Nations of North America - Joel Garreau 1981
Free Spirits: Annals of the Insurgent Imagination - Paul Buhle, ed. (City Lights) In These Times May 24-30, 1983
America's Quest for the Ideal Self: Dissent and Fulfillment in the 60s and 70s - Peter Clecak (UC Irvine professor of social thought and comparative culture), Oxford University Press 1983
The Haight-Ashbury: A History - Charles Perry 1984
Who Spoke Up? American Protest Against the War in Vietnam 1963-1975 - Zaroulis and Sullivan 1984
Uncovering the Sixties: The Life & Times of the Underground Press - Abe Peck 1985
Not Fade Away - Jim Dodge (wrote FUP) 1987 novel
Somewhere Off the Coast of Maine - Ann Hood 1987 novel - three former flower children and their present-day family life
Down & In: Life in the Underground - Ronald Sukenick 1987
Good Intentions: A Novel About Revolution - Don Paul 1987
Freedom Song: A Personal Story of the 1960s Civil Rights Movement - Mary King 1987
The Summer of Love: A photo-documentary by Gene Anthony 1987
Democracy Is In the Streets - James Miller 1987 (SDS)
The Year of the Barricades: A Journey Through 1968 - David Caute 1988
Chicago '68 - David Farber 1988
1968: A Student Generation in Revolt - Ronald Fraser et al 1988
1968 in America: Music, Politics, Chaos, Counterculture, and the Shaping of a Generation - Charles Kaiser 1988
The Way We Were: 1963 The Year Kennedy Was Shot - Robert MacNeil 1988
1968 - A Student Generation in Revolt (an anthology of oral histories) - Pantheon Books 1988
Remembering America: A Voice From the Sixties - Richard N. Goodwin (wrote Kennedy speeches) 1988
The Art of Rock - Paul D. Guishken 1988
Aquarius Revisited: Seven Who Created the Sixties Counterculture That Changed America - Peter O. Whitmer 1988
From Camelot to Kent State: The Sixties Experience in the Words of Those Who Lived It - Joan Morrison 1988
Turning Point: 1968 - Irwin Unger & Debi Unger (Scribner's) 1988
Baby Boomers - Paul C. Light 1988
Destructive Generation: Second Thoughts about the 60s - Peter Collier & David Horowitz 1989
Sixties People -Jane Stern and Michael Stern 1990
The Further Inquiry - Ken Kesey 1990
On The Bus - Paul Perry and Ken Babbs 1990

Publication dates unknown:
Person / Planet
Psychotic Reactions and Carburetor Dung - Lester Bangs, edited by Greil Marcus - rock criticism
The Simple Life: Plain Living and High Thinking in American Culture - David E. Shi (Jefferson, Thoreau, Lewis Mumford, Scott Nearing, hippies)
Acid Dreams - Martin Lee & Bruce Schain
The Sixties Papers - _______ Albert
When the Music Mattered: Rock in the 1960s
Freedom in the Air: Song Movements of the Sixties
Street Fighting Years - Tariq Ali
Reunion: A Memoir - Tom Hayden
Dream Time: Chapter From the Sixties - Geoffrey O'Brien
Appetite For Change: How the Counterculture Took On the Food Industry 1966-1988 - Warren J. Belasco
Sophisticated Rebels: The Political Culture of European Dissent, 1968-1987 - H, Stuart Hughes (Harvard Univ Press)