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Silk Road was an online black market and the first modern darknet market, best known as a platform for selling illegal drugs. As part of the dark web, it was operated as a Tor hidden service, such that online users were able to browse it anonymously and securely without potential traffic monitoring. The website was launched in February 2011; development had begun six months prior. Initially there were a limited number of new seller accounts available; new sellers had to purchase an account in an auction. Later, a fixed fee was charged for each new seller account. In October 2013, the Federal Bureau of Investigation (FBI) shut down the website and arrested Ross William Ulbricht under charges of being the site's pseudonymous founder "Dread Pirate Roberts". On 6 November 2013, Silk Road 2.0 came online, run by former administrators of Silk Road. It too was shut down, and the alleged operator was arrested on 6 November 2014 as part of the so-called "Operation Onymous”. Ulbricht was convicted of eight charges related to Silk Road in U.S. Federal Court in Manhattan and was sentenced to life in prison without possibility of parole.

The dark web is the World Wide Web content that exists on darknets; overlay networks which use the Internet but require specific software, configurations or authorization to access. The dark web forms a small part of the deep web, the part of the Web not indexed by search engines, although sometimes the term "deep web" is mistakenly used to refer specifically to the dark web. The darknets which constitute the dark web include small, friend-to-friend peer-to-peer networks, as well as large, popular networks like Tor, Freenet, and I2P, operated by public organizations and individuals. Users of the dark web refer to the regular web as Clearnet due to its unencrypted nature. The Tor dark web may be referred to as onionland, a reference to the network's top level domain suffix .onion and the traffic anonymization technique of onion routing.