The inaugural festival occurred from August 22–24, 2008, with Radiohead as the first band to play after dark. It included more than 60 musical acts, as well as several art installations. The festival grounds included the Polo Fields, Hellman's Hollow/Speedway Meadow, and Lindley Meadow. Bringing in 40,000 to 60,000 attendees a day, the inaugural festival was mostly a success; however, it was criticized for its lack of crowd control and disruption to the normally quiet Richmond and Sunset District neighborhoods. The second edition of the festival was held between August 28–30, 2009, and streamed live on YouTube via the festival's YouTube account. It was not as successful as the inaugural year with a smaller turnout. Beastie Boys were scheduled to headliner, however, they dropped out of the lineup a month before the festival after Adam Yauch was diagnosed with cancer. Promoters scaled the event down to 40 total acts over two days for the third year. During the 2014 event, San Francisco police seized hundreds of counterfeit wristbands used by scalpers. This resulted in an adoption of radio frequency identification wristbands for 2015, along with an accusation that Fantastic Negrito was selling illegal VIP passes to the event.
The 2019 iteration became the first major music festival to offer legal cannabis for sale after the San Francisco Office of Cannabis granted a temporary sales permit to Outside Lands. The area was known as "Grass Lands" and sold more than $1 million in cannabis products such as edibles, vaping cartridges and joints over the three-day event. 28 brands including Cresco Labs, PAX, Eaze, Kiva Confections, Flow Kana, Openvape and Bloom Farms sold items such as cannabis-infused drinks, edibles, dabs, prerolls and disposable pods. San Francisco-based brands Green Door, Lady Chatterley Delivery, Flower to the People and Posh Green Collective were also available in Grass Lands. There were zero requests for medical transport in the designated area, and all participants were required to throw away any alcoholic beverages before entering and show a 21+ identification.
Other attractions
Outside Lands also features attractions that focus around food, wine, and art. There is a wine lands portion of the festival that allows people to purchase tickets and sample wine from many different vendors. There are also areas that offer separate entertainment, including a sports lounge, an arcade/bar, and various food and art vendors. Despite its large environmental footprint, the festival has attempted to promote strategies of being eco-friendly. There are solar power stages, a refillable water program, a waste diversion program, a recycling program, and bike valet parking program. There have also been workshops to educate about organic food and farming.
