diff --git a/README.md b/README.md
index 6f454d13..6c44dfa1 100644
--- a/README.md
+++ b/README.md
@@ -24,6 +24,91 @@ View at: http://localhost:4567
 It is recommended to also run `gem install thin`, which Sinatra will
 pick up if available.
 
+## Table of Contents
+
+* [Sinatra](#sinatra)
+    * [Table of Contents](#table-of-contents)
+    * [Routes](#routes)
+    * [Conditions](#conditions)
+        * [Return Values](#return-values)
+        * [Custom Route Matchers](#custom-route-matchers)
+        * [Static Files](#static-files)
+        * [Views / Templates](#views--templates)
+            * [Literal Templates](#literal-templates)
+        * [Available Template Languages](#available-template-languages)
+            * [Haml Templates](#haml-templates)
+            * [Erb Templates](#erb-templates)
+            * [Builder Templates](#builder-templates)
+            * [Nokogiri Templates](#nokogiri-templates)
+            * [Sass Templates](#sass-templates)
+            * [SCSS Templates](#scss-templates)
+            * [Less Templates](#less-templates)
+            * [Liquid Templates](#liquid-templates)
+            * [Markdown Templates](#markdown-templates)
+            * [Textile Templates](#textile-templates)
+            * [RDoc Templates](#rdoc-templates)
+            * [Radius Templates](#radius-templates)
+            * [Markaby Templates](#markaby-templates)
+            * [RABL Templates](#rabl-templates)
+            * [Slim Templates](#slim-templates)
+            * [Creole Templates](#creole-templates)
+            * [CoffeeScript Templates](#coffeescript-templates)
+            * [Stylus Templates](#stylus-templates)
+            * [Yajl Templates](#yajl-templates)
+            * [WLang Templates](#wlang-templates)
+        * [Accessing Variables in Templates](#accessing-variables-in-templates)
+        * [Templates with `yield` and nested layouts](#templates-with-yield-and-nested-layouts)
+        * [Inline Templates](#inline-templates)
+        * [Named Templates](#named-templates)
+        * [Associating File Extensions](#associating-file-extensions)
+        * [Adding Your Own Template Engine](#adding-your-own-template-engine)
+    * [Filters](#filters)
+    * [Helpers](#helpers)
+        * [Using Sessions](#using-sessions)
+        * [Halting](#halting)
+        * [Passing](#passing)
+        * [Triggering Another Route](#triggering-another-route)
+        * [Setting Body, Status Code and Headers](#setting-body-status-code-and-headers)
+        * [Streaming Responses](#streaming-responses)
+        * [Logging](#logging)
+        * [Mime Types](#mime-types)
+        * [Generating URLs](#generating-urls)
+        * [Browser Redirect](#browser-redirect)
+        * [Cache Control](#cache-control)
+        * [Sending Files](#sending-files)
+        * [Accessing the Request Object](#accessing-the-request-object)
+        * [Attachments](#attachments)
+        * [Dealing with Date and Time](#dealing-with-date-and-time)
+        * [Looking Up Template Files](#looking-up-template-files)
+    * [Configuration](#configuration)
+        * [Configuring attack protection](#configuring-attack-protection)
+        * [Available Settings](#available-settings)
+    * [Environments](#environments)
+    * [Error Handling](#error-handling)
+        * [Not Found](#not-found)
+        * [Error](#error)
+    * [Rack Middleware](#rack-middleware)
+    * [Testing](#testing)
+    * [Sinatra::Base - Middleware, Libraries, and Modular Apps](#sinatrabase---middleware-libraries-and-modular-apps)
+        * [Modular vs. Classic Style](#modular-vs-classic-style)
+        * [Serving a Modular Application](#serving-a-modular-application)
+        * [Using a Classic Style Application with a config.ru](#using-a-classic-style-application-with-a-configru)
+        * [When to use a config.ru?](#when-to-use-a-configru)
+        * [Using Sinatra as Middleware](#using-sinatra-as-middleware)
+        * [Dynamic Application Creation](#dynamic-application-creation)
+    * [Scopes and Binding](#scopes-and-binding)
+        * [Application/Class Scope](#applicationclass-scope)
+        * [Request/Instance Scope](#requestinstance-scope)
+        * [Delegation Scope](#delegation-scope)
+    * [Command Line](#command-line)
+    * [Requirement](#requirement)
+    * [The Bleeding Edge](#the-bleeding-edge)
+        * [With Bundler](#with-bundler)
+        * [Roll Your Own](#roll-your-own)
+        * [Install Globally](#install-globally)
+    * [Versioning](#versioning)
+    * [Further Reading](#further-reading)
+
 ## Routes
 
 In Sinatra, a route is an HTTP method paired with a URL-matching pattern.
diff --git a/Rakefile b/Rakefile
index b14a0d15..8ead3d86 100644
--- a/Rakefile
+++ b/Rakefile
@@ -126,6 +126,20 @@ task :authors, [:commit_range, :format, :sep] do |t, a|
   puts authors.sort_by { |n,c| -c }.map { |e| a.format % e }.join(a.sep)
 end
 
+desc "generates TOC"
+task :toc, [:readme] do |t, a|
+  a.with_defaults :readme => 'README.md'
+
+  def self.link(title)
+    title.downcase.gsub(/(?!-)\W /, '-').gsub(' ', '-').gsub(/(?!-)\W/, '')
+  end
+
+  puts "* [Sinatra](#sinatra)"
+  File.binread(a.readme).scan(/^##.*/) do |line|
+    puts line.gsub(/#(?=#)/, '    ').gsub('#', '*').gsub(/(?<=\* )(.*)/) { "[#{$1}](##{link($1)})" }
+  end
+end
+
 # PACKAGING ============================================================
 
 if defined?(Gem)