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WebGoat is a deliberately insecure J2EE web application maintained by OWASP designed to teach web application security lessons. In each lesson, users must demonstrate their understanding of a security issue by exploiting a real vulnerability in the WebGoat application. For example, in one of the lessons the user must use SQL injection to steal fake credit card numbers. The application is a realistic teaching environment, providing users with hints and code to further explain the lesson.

Wapiti allows you to audit the security of your web applications.
It performs "black-box" scans, i.e. it does not study the source code of the application but will scans the webpages of the deployed webapp, looking for scripts and forms where it can inject data.
Once it gets this list, Wapiti acts like a fuzzer, injecting payloads to see if a script is vulnerable.

Wfuzz is a tool designed for bruteforcing Web Applications, it can be used for finding resources not linked (directories, servlets, scripts, etc), bruteforce GET and POST parameters for checking different kind of injections (SQL, XSS, LDAP,etc), bruteforce Forms parameters (User/Password), Fuzzing,etc.

DirBuster searches for hidden pages and directories on a web server. Sometimes developers will leave a page accessible, but unlinked; DirBuster is meant to find these potential vulnerabilities.

Grendel-Scan is an open-source web application security testing tool. It has automated testing module for detecting common web application vulnerabilities, and features geared at aiding manual penetration tests. The only system requirement is Java 5; Windows, Linux and Macintosh builds are available.

Websecurify is an advanced testing solution built to quickly and accurately identify web application security issues.

The OpenSSL Project is a collaborative effort to develop a robust, commercial-grade, full-featured, and Open Source toolkit implementing the Secure Sockets Layer (SSL v2/v3) and Transport Layer Security (TLS v1) protocols as well as a full-strength general purpose cryptography library. The project is managed by a worldwide community of volunteers that use the Internet to communicate, plan, and develop the OpenSSL toolkit and its related documentation.

The basic principle behind wXf is to collect and place into a framework, all of the various scripts that web security testers create on a per-engagement scenario. This tool is like metasploit for webapps.

httptunnel creates a bidirectional virtual data connection tunnelled in HTTP requests.

A Firefox extension that demonstrates HTTP session hijacking attacks.