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43 Rare Woodstock Photos That Show Just How Crazy Woodstock Really Was

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What was supposed to be three days of peace love, and music celebrated on an obscure dairy farm in the town of Bethel, New York in the summer of ’69, turned out to be the most iconic music event of all time. Yes, we’re talking about Woodstock, the pivotal moment in music history that began on August 15, 1969.

We’ve collected extremely rare Woodstock photos that capture what it was really like to be there. From 32 iconic performances, over 400,000 excited fans, traffic jams, psychedelic vans, bohemian and hippie fashion, rain, sunshine, and a whole lot of peace and love ― that was the name of the game at Woodstock, and it changed the lives of everyone who was and wasn’t there.

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1. Arts & Crafts

The Woodstock Music & Art Fair festival wasn’t called that for no reason. The festival was a place for young souls to express their creativity and self-expression through music and art, like this bohemian woman adorned with a leather crop top, headband, and arm bracelet.

She parked herself down on the grass to weave her leather-tasseled tapestry. Perhaps she handed it out to other fellow festival-goers or even sold a few. Whichever way, her style was certainly in tune with the spirit of Woodstock.

2. Peace and Bubbles

Nearly 500,000 people flooded in droves to Woodstock to get a slice of the unique and eclectic experience of unity and love. While most hung out at the festival with a partner or a group of people, others preferred to take part in the fun on their own.

Pictured here is a woman named Jackie Barg sitting on the ground blowing bubbles into the crowd while enjoying her own company. This free-spirited concertgoer was probably having some fun while waiting for the next performer to appear on stage.

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3. Food For Love

It was common for the crowds at Woodstock to share their food, water, and clothing with their neighbors and fellow festival-goers, as sharing was one of the main philosophies the festival stood for. This incredibly rare photo captures just that with this young woman preparing food for the rest of the Woodstock community.

Unfortunately, there was a huge shortage of food because the number of people that showed up at Woodstock far exceeded the number anyone could have anticipated. Many people didn’t want to lose their spot on the field or have to trudge through the crowds to find food, so they set up free stands and banded together to feed everyone.

4. Some Shut-Eye

Nearly half a million people attended Woodstock, so it’s no surprise that there were major traffic jams and a lack of space within the confines of Max Yasgur’s dairy farm, where the festival was held.

Many people, like this woman, slept on their motorbikes or vehicles because it was too hot to sleep inside them. The lucky ones built tents and temporary shelters with sleeping bags, but when space ran out, the rest had to retire to their vans and cars if they could reach them. Some even had to stay in their vehicles when the traffic blocked the way.

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5. Rocking with Jimi Hendrix

Jimi Hendrix was one of the 32 acts to perform at Woodstock, and boy did he put on one hell of a show donning a white leather and blue-beaded fringed jacket. The icon was actually the last to perform at the festival for a crowd of 30,000 onlookers as many of the music-loving concertgoers had already gone home because of the rain delays.

The ones who waited in anticipation for Hendrix’s two-hour performance with his new band Gypsy Sun and Rainbows were certainly thrilled they waited, as it has gone done in history as a defining moment of the ’60s. Hendrix might have been the last act to perform, but he was the highest paid and earned himself a nice sum of $18,000.

6. Wrapped Up in Love

Woodstock gave the people something to believe in and hold onto during a very tumultuous political era, which is why this photo became one of the most famous from the festival. Now both 69 years old, Bobbi Kelly and her then-boyfriend Nick Ercoline became the poster children of Woodstock wrapped in an embrace with the sun rising in the background.

The image represented the love, peace, and individuality everyone felt at the three-day festival; a love so strong that this couple went on to marry and have two children. Burk Uzzle of Magnum Agency snapped the photo without the couple noticing. Uzzle recalled how Gracie Slick of Jefferson Airplane was performing at the break of dawn when this couple “magically stood up and hugged.” After they kissed and hugged, Kelly smiled and leaned her head on his shoulder.

7. Sway Your Hair Like You Don’t Care

Advertised as a “weekend in the country,” Woodstock was so much more than that. It was three days of non-stop love, peace, partying, rock and roll, and fun with 32 performances by A-list musicians. As Joni Mitchell said, “Woodstock was a spark of beauty where half-a-million kids saw that they were part of a greater organism.”

Pictured here are two women dancing and swaying to the beat, and literally letting their hair down. Peace, love, and acceptance were photographed from every angle at the music festival. The people in attendance believed music could change the world and that the hippie movement was more than just Kumbayas and daisies.

8. Hanging with The Pearl

Otherwise known as The Pearl, Janis Joplin will forever be remembered as one of the best female rockers of all time. Joplin performed on the second day of Woodstock rocking a colorful and psychedelic dress. She didn’t know about the festival until a few days before, but luckily for the crowd, she found out just in time and was one of the biggest names to perform.

Joplin wasn’t aware of how big the festival would be and told her band it’d be just another gig. However, when she and her band, along with a pregnant Joan Baez, were flown into Woodstock by helicopter, she saw the sheer size of the crowds and became giddy with nerves. She remained at the festival until the end.

9. Gypsy Souls

The Woodstock Music & Art Fair attracted a fair share of spiritual and free-spirited people who believed that love was the only religion man needed to achieve world peace — with the help of some tarot cards and psychic readings that is.

Here we see a woman dressed in a paisley bohemian dress reading another girl’s palm with a set of tarot cards laid out on a tree trunk. She must have received some interesting news judging by that smile on her face.

10. The Who’s Who

Woodstock gained a lot of momentum even before it happened, so it’s no surprise that some famous faces rocked along to the music with the rest of the crowd, such as German actress and model Veruschka von Lehndorff.

Veruschka was extremely popular in the ’60s. She rose to fame at the age of 20 while studying art in Florence, where was discovered by photographer Ugo Mulas. Here we see the model dancing to the beat and having a good time at Woodstock.

11. Flower Child

It’s no secret that Woodstock was no place for discrimination against gender or race, but did you know that all ages were welcome too? This captivating photograph of this happy dancing young girl pays tribute to how much fun Woodstock was for all the people present at the iconic musical festival. Imagine the memories she must carry from that weekend!

Not only were tons of children parts of the partying masses; some were even born at this historical event. Two births were recorded at Woodstock ― one in a car stuck in the traffic jam on the way to the festival and another in hospital after the mother was airlifted by helicopter.

12. Tie-Dye for the Win!

Following the fashion direction of rock stars such as Janis Joplin and John Sebastian in the late ’60s, tie-dye clothing became more than just a fashion trend; it was a lifestyle choice. It’s no surprise then that this psychedelic clothing was prevalent at Woodstock.

This colorful fashion choice was all the craze at the music festival with lots of stands selling different kinds of designs and items. If you weren’t sporting your rainbow swirled patterned shirt, then you weren’t part of the crowd!

13. Follow the Groovy Brick Road

There were many paths to follow at Woodstock, but you were sure in for one hell of a psychedelic ride no matter which one you chose. We love these whimsical signs hanging on the trees and wish we could have one like them in our own homes!

It’s safe to assume that at the groovy way, one would have encountered people sporting afros and bell-bottomed jeans, a fad that continued into the impending disco era, while the gentle path was for those yoga-loving spiritual gurus. Namaste!

14. The Star and the Groupie

Pictured here is Jefferson Airplane’s lead signer Grace Slick hanging out backstage with Sally Mann, wife of the band’s drummer, Spencer Dryden. Just like the audience enjoyed the music, so too did the other performers.

When talking to the Rolling Stone magazine about her experiences at Woodstock, Slick said she remembers taking a helicopter to get to the music festival because the roads were so jammed. Until Jefferson Airplane performed on the second day, she recalled sitting around smoking and drinking wine with Mann and the other band members.

15. When Life Gives You Instruments, Make Music!

There was truly a feeling of unity and love for the festival-goers who came to enjoy the rock and roll music and festivities for three days straight, so much so, that when there were breaks between performances they made their own music.

Pictured here is a woman playing the flute to the beating of a drum. You can see the fiery passion in the drummer’s eye, a passion that everyone around him shared. Peace, love, and partying could be found at every angle you looked at during Woodstock.

16. Taking Notes

Tim Hardin performed his hit “If I Were a Carpenter” solo on the first day of Woodstock, along with other songs performed with his band. For his incredible performance, Hardin was paid $2,000, which wasn’t as much as some of the other artists performing at the music festival.

This epic photograph catches him in action, but not on stage. He took some quiet time to jot down notes and possibly compose some music and lyrics. He definitely looks deep in thought, that’s for sure!

17. The Queen of Boho

Concertgoers at Woodstock felt comfortable experimenting with all kinds of hippie and bohemian fashion as well as colors and textures, like this stylish woman. This photo showcases the beauty of accessorizing in all its glory from head to toe.

With her floppy hat, headpiece, bold makeup with sequins, and thick beaded jewelry, this woman represents freedom of expression and individuality. Much like music was a big thing at Woodstock, so too was fashion and art.

18. Hail the Almighty Rain Makers!

If you thought that dancing and partying were the only things that took place at the Woodstock music festival, then you’re sorely mistaken. Add to that spiritual rain dancing and you’ve got the whole package covered.

This group of people were performing a tribal rain dance, and it clearly worked because on-and-off torrential rains came down on the festival, breaking the hot August afternoon sun and creating a very muddy experience. The hippies didn’t mind much!

19. A Muddy Business

The outdoor music festival saw lots of wet weather between the bright sunshine. Not only did this cause technical delays, but also quite a messy business as seen in this amazing photograph. This couple is seen performing a bit of team work twisting out the water of their soaked blanket. We can imagine no one got much sleeping done at Woodstock.

The rain caused lots of mud baths and dirt, but that didn’t stop the 32 acts from performing for the tremendously eager audience. Come rain or shine, the crowd didn’t seem to mind the mud at all. Lots of hippies actually threw off their shoes and soaked their feet in the dirt. Some, however, did come prepared with raincoats, umbrellas, and plastic sheets.

20. One Love

If no other photograph captures the sheer joy and ecstasy that was Woodstock, then this one certainly does. The organizers of the festival were worried the hippies and heavy metal music would cause violence, but there was nothing of the sort reported from the music festival.

For three days straight, all that was palpable at Woodstock was unity, peace, happiness, and a sense of freedom. Look at this crowd clapping their hands in the air to the music with massive smiles on their faces. We can feel the excitement emanating from this image.

21. Rocking the Daisies

Did somebody say daisy? We all know daisies are the ultimate symbol of everything hippie and groovy, but the crowd at Woodstock really believed and stood for peace and love like this happy couple, locked in a loving embrace.

The vibe at this music festival was electric, and anyone who was there has described how they never experienced anything like it again. The Doors and other famous bands forever regretted turning down their invite or not being able to make it to Woodstock.

22. Fashion Forward

Besides for the long beaded necklaces and leather clothing and accessories, people at Woodstock let their hair take on a natural and untamed styles. Most of the women sported long hair parted in the middle and sometimes accented with bangs, while the men loved to grow afros or long beards.

This festival-goer exudes a sense of artistic freedom wearing a sleek, all-black look with carefully selected leather accents like her belt and arm bracelet. Woodstock was an opportunity for everyone to showcase their individual style, which sometimes included some questionable trends like nudity.

23. Psychedelic Vans

Many of the people who attended Woodstock camped out on the top of their psychedelic vans, as the living conditions at the music festival got pretty tough. We must say it looks pretty fun, whether it was planned or not.

In fact, this pivotal moment in pop musical history is marked by how the concertgoers camped out in their colorful vans. They couldn’t really move because of how many extra people attended and how Woodstock ending up lasting four days instead of three.

24. Picture Perfect

While all the magic was happening on stage, there were even more magical amoments captured among the crowds at Woodstock. This beautiful photograph of a couple looking distracted while posing for a picture shows how almost every moment at the festival was fit for a frame.

Was this blonde boho concertgoer staring at an airplane, just taking in the moment, or looking at a psychedelic formation in the sky? We’ll never know, but we certainly love the burlap dress she was rocking and her partner’s afro hairdo.

25. One Big, Happy Family

From the adults to the little kids, everyone was loving the atmosphere and the music at Woodstock. Lazing about on the grass listening to the music was one of the crowd’s favorite pastimes at the outdoor festival.

This image was taken by Rolling Stones magazine’s private photographer Baron Wolman. Rolling Stone was one of the only media outlets allowed official and unlimited access to the festival. Everyone loved the magazine so they allowed Wolman to take pictures, such as this woman showing a peace sign.

26. A Celestial Sound

Sri Swami Satchidananda, an Indian religious teacher and spiritual master, gave the opening speech after Richie Havens performed his act kicking off the Woodstock music festival. He addressed almost half a million people with a very poignant and empowering message.

“My Beloved Brothers and Sisters we can just feel the vibes. Music is a celestial sound, and it is the sound that controls the whole universe, not atomic vibrations. Sound energy, sound power, is much, much greater than any other power in this world. And, one thing I would very much wish you all to remember is that with sound, we can make—and at the same time, break,” he bellowed into the mic.

27. The Faces Behind the Magic

Woodstock was held at Max Yasgur’s 600-acre dairy farm in the Catskill Mountains of New York State. It was near White Lake in the town of Bethel, 43 miles (70km) away from the town of Woodstock. However, the festival was called Woodstock as the investment group that backed the concert was called Woodstock Ventures.

Yasgur was a nice farmer, the son of Russian Jewish immigrants who offered his farm to the festival organizers. During the festival, Yasgur even came onstage to say hi to the crowd. Many of his neighbors scorned him for hosting the festival and he was no longer welcome at the town’s general store. He was even sued by his neighbors for property damage caused by the concertgoers. Sadly, he died just four years after Woodstock at the age of 53 and became one of the only non-musicians to land a full page obituary in Rolling Stones magazine.

28. Couple Goals

This couple epitomizes natural beauty with their sweet smiles and boho fashion. Seems like they were posing for a picture outside the tent they constructed for the weekend, looking all happy and ready to see the likes of Jimi Hendrix, Janis Joplin, Santana, Joan Baez, and many other legends.

We really love this woman’s choice of clothing. The colors she chose fit in perfectly with the festive atmosphere of Woodstock. Talking about fashion, here’s a fun fact for you: If you were to put all the striped T-shirt material and blue jeans the festival attendees were wearing, there would have been 10 million yards of it.

29. Some Morning Yoga

Sri Swami Satchidananda and all his spiritual warriors practiced yoga in the morning on the vast lawns to get their daily dose of stretches in between the performances. Judging by some of their poses, these people were naturals!

Woodstock was a celebration of the mind, spirit, and body, and yoga fit right in with those pillars of belief. This photograph makes us want to meditate too or even transport back to that beautiful time in our imaginations.

30. Milk, Please

Woodstock took place on Max Yasgur’s dairy farm in Bethel, New York, which meant there were lots of animals hanging around and the concertgoers took full advantage of that. On the way to the festival, some of them decided to quench their thirst with some fresh cow milk.

This scene turned into quite the spectacle with other people gathered on the side of the road to witness the guys milking the cow. We’re sure they shared the fresh produce with all the onlookers and fellow festival-goers.

31. Deserted Dreamers

The roads to Yasgur’s dairy farm became so jammed that many people had to abandon their cars or hitchhike with others. Some even jumped onto the car roofs of moving vehicles just to get to what became a once-in-a-lifetime rock festival.

Here we have a man strumming his guitar to serenade his disappointed girlfriend with his own rock and roll music, as they missed the concert because of the backed up roads. At least he tried to give her his rendition of what he thought the festival would be like.

32. Free Festival

Woodstock wasn’t supposed to be that big of an event, so when over 400,000 people showed up, no one was really prepared for the magnitude of it all. Before the festival, the organizers managed to sell 100,000 tickets which means more than 300,000 showed up without tickets.

The late change in the venue didn’t give the organizers enough time to deal with the influx of people. The audience started to arrive by the tens of thousands two days before the music festival began and walked through the gaps in the fences. The organizers eventually decided to make the concert free. And to think this all went down on a small dairy farm!

33. Peace & Love

With nearly half a million people in the crowd, it was pretty hard to see the stage at times. Well, not if you got to enjoy the show on the shoulders of your friends like this happy lady.

This photograph of a woman loving the music and holding up peace signs at Woodstock definitely captures the camaraderie everyone experienced at this incredible music festival. People didn’t only throng to Woodstock for the music, but also for the good vibes of peace and community felt at this popular event.

34. One Flew Over the Cuckoo’s Nest

This hippie girl probably wanted to take a break from the music at the Woodstock Music & Art Fair and went venturing on Max Yasgur’s farm to have a look at the baby chicks in the chicken coop.

Judging by the expression on her face, she was having a lot of fun staring at the little yellow birds. That’s the cool part about having a music festival on a farm; you get to play with the animals!

35. Smile for Me, Baby!

You don’t get more hippie than this woman donning her flower wreath, floral tank top, and sun pendant necklace. This was a the dress code for a lot of concertgoers at Woodstock. She’s also pretty close to the stage, which makes this photograph even better to look at.

People flocked to what was supposed to be the most iconic music festival of the ’60s, but became one of the most profound events in history. It was an event that celebrated individuality, music, art, fashion, and freedom of expression.

36. Peaceful Protest

Woodstock stood for nonviolence, peace, love, openness, and cultural acceptance. Most of the people in attendance were part of the hippie movement, which opposed the Vietnam War, and some of the performers reflected this viewpoint in their anti-war speeches.

Unlike many other music concerts of the time, Woodstock was free of physical altercations and violence when it came to protesting and demonstrating for a cause. This animal lover certainly didn’t seem to be bothering anyone in the crowd.

37. In the Zone

This long-haired and bearded man perched himself on top of a tree house platform to strum on this guitar during the Woodstock Music & Art Fair. Many concertgoers didn’t only come to enjoy the performances; they also came to play their own their instruments to keep themselves and others around them entertained.

The spirit of this music festival was to promote a togetherness of love, peace, and rock and roll, so therefore many of the people in attendance were in their element to just sit around for a whole weekend playing on their instruments while enjoying the awesome environment.

38. A Weekend to Remember

Music concerts are about enjoying time with friends and family in the outdoors. Woodstock was that and so much more if this rare photograph is anything to go by. Everyone seemed to be settled in their spot in the forest.

It’s clear these people were there to stay for the entire weekend with all their clothes hanging on the trees. The hippies at Woodstock were very nature-loving individuals, which is why most of them seemed very content sitting in the dirt.

39. A Different Perspective

We’re sure this guy’s book made an interesting read, but reading it perched in the sky must have made it even more exhilarating. That, or he just wanted the best view at Woodstock and decided to catch up on some reading between the performances.

We really want to know how in the world he got up there in the first place?! Also, the fact that he managed to balance himself without plummeting to the bottom is seriously admirable. These kinds of eccentric occurrences and sites were quite commonplace at Woodstock.

40. Crowd-Surfing

Woodstock was definitely an adult playground with all sorts of fun and interesting activities and incidents going down. Crowd-surfing and getting thrown up in the air in a sheet of fabric were just a few of the favorite pastimes at this epic music festival.

This expression on this woman’s face gives everything away: she’s slightly frightened, but loving it at the same time. When people weren’t relaxing on the grass and in the woods, they were having a great time jamming in the crowd by the stage.

41. Dancing in the Rain

Despite the rainy and muddy conditions, the crowds at Woodstock were loving every bit of the weekend. Hippies aren’t particularly people who seek out luxury and comfort, and therefore many of them took off their shoes and traipsed in the mud barefoot.

Everyone in the photograph looks pretty content in spite of the gloomy weather and muddy ditches. Luckily for them, there were also bouts of warm sunshine for them to party in during the weekend music festival.

42. An Obstacle Course

Security wasn’t really tight at Woodstock, which is one reason it became a free festival. These men in the audience wanted a better view of the stage, so they decided to try their luck and sit on some of the stage scaffolding equipment.

The attendees at Woodstock were pretty much in luck with no reported violent or security incidences. Out of the 400,000 concertgoers in attendance, three were only two deaths recorded at the festival. One person died from a substance overdose, while another was accidentally run over by a tractor while sleeping in a sleeping bag in a nearby hay field.

43. Medical Aid

While the mood at Woodstock was certainly anti-war, if it wasn’t for the U.S. Army, there would have been lots of medical emergencies. Military personnel flew in food, medical supplies, and medical teams into the festival.

Over 45 doctors were on standby at the music convert without pay. They liked what the festival stood for and chose to help. During that weekend, the festival became the third largest city in New York State, but owing to the lack of much needed basic amenities, the governor of New York Nelson Rockefeller declared Woodstock a disaster area. The health department recorded 5,162 medical cases, including four miscarriages. Despite all of this, Time magazine deemed the festival, “The greatest peaceful event in history.”

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