diff --git a/lib/jekyll/page.rb b/lib/jekyll/page.rb
index c4143424..2e996308 100644
--- a/lib/jekyll/page.rb
+++ b/lib/jekyll/page.rb
@@ -93,24 +93,25 @@ module Jekyll
         "url"        => File.join(@dir, self.url),
         "content"    => self.content })
     end
+    
+    # Obtain destination path.
+    #   +dest+ is the String path to the destination dir
+    #
+    # Returns destination file path.
+    def destination(dest)
+      # The url needs to be unescaped in order to preserve the correct filename
+      path = File.join(dest, @dir, CGI.unescape(self.url))
+      path = File.join(path, "index.html") if self.url =~ /\/$/
+      path
+    end
 
     # Write the generated page file to the destination directory.
-    #   +dest_prefix+ is the String path to the destination dir
-    #   +dest_suffix+ is a suffix path to the destination dir
+    #   +dest+ is the String path to the destination dir
     #
     # Returns nothing
-    def write(dest_prefix, dest_suffix = nil)
-      dest = File.join(dest_prefix, @dir)
-      dest = File.join(dest, dest_suffix) if dest_suffix
-      FileUtils.mkdir_p(dest)
-
-      # The url needs to be unescaped in order to preserve the correct filename
-      path = File.join(dest, CGI.unescape(self.url))
-      if self.url =~ /\/$/
-        FileUtils.mkdir_p(path)
-        path = File.join(path, "index.html")
-      end
-
+    def write(dest)
+      path = destination(dest)
+      FileUtils.mkdir_p(File.dirname(path))
       File.open(path, 'w') do |f|
         f.write(self.output)
       end
diff --git a/lib/jekyll/post.rb b/lib/jekyll/post.rb
index b1a2a63d..7747eff4 100644
--- a/lib/jekyll/post.rb
+++ b/lib/jekyll/post.rb
@@ -177,22 +177,25 @@ module Jekyll
 
       do_layout(payload, layouts)
     end
+    
+    # Obtain destination path.
+    #   +dest+ is the String path to the destination dir
+    #
+    # Returns destination file path.
+    def destination(dest)
+      # The url needs to be unescaped in order to preserve the correct filename
+      path = File.join(dest, CGI.unescape(self.url))
+      path = File.join(path, "index.html") if template[/\.html$/].nil?
+      path
+    end
 
     # Write the generated post file to the destination directory.
     #   +dest+ is the String path to the destination dir
     #
     # Returns nothing
     def write(dest)
-      FileUtils.mkdir_p(File.join(dest, dir))
-
-      # The url needs to be unescaped in order to preserve the correct filename
-      path = File.join(dest, CGI.unescape(self.url))
-
-      if template[/\.html$/].nil?
-        FileUtils.mkdir_p(path)
-        path = File.join(path, "index.html")
-      end
-
+      path = destination(dest)
+      FileUtils.mkdir_p(File.dirname(path))
       File.open(path, 'w') do |f|
         f.write(self.output)
       end
diff --git a/lib/jekyll/site.rb b/lib/jekyll/site.rb
index 331b6c07..55b5c9d4 100644
--- a/lib/jekyll/site.rb
+++ b/lib/jekyll/site.rb
@@ -79,6 +79,7 @@ module Jekyll
       self.read
       self.generate
       self.render
+      self.cleanup
       self.write
     end
 
@@ -151,6 +152,36 @@ module Jekyll
     rescue Errno::ENOENT => e
       # ignore missing layout dir
     end
+    
+    # Remove orphaned files and empty directories in destination
+    #
+    # Returns nothing
+    def cleanup
+      # all files and directories in destination, including hidden ones
+      dest_files = []
+      Dir.glob(File.join(self.dest, "**", "*"), File::FNM_DOTMATCH) do |file|
+        dest_files << file unless file =~ /\/\.{1,2}$/
+      end
+
+      # files to be written
+      files = []
+      self.posts.each do |post|
+        files << post.destination(self.dest)
+      end
+      self.pages.each do |page|
+        files << page.destination(self.dest)
+      end
+      self.static_files.each do |sf|
+        files << sf.destination(self.dest)
+      end
+      
+      # adding files' parent directories
+      files.each { |file| files << File.dirname(file) unless files.include? File.dirname(file) }
+      
+      obsolete_files = dest_files - files
+      
+      FileUtils.rm_rf(obsolete_files)
+    end
 
     # Write static files, pages and posts
     #
diff --git a/lib/jekyll/static_file.rb b/lib/jekyll/static_file.rb
index 01f8ee62..5509db75 100644
--- a/lib/jekyll/static_file.rb
+++ b/lib/jekyll/static_file.rb
@@ -52,12 +52,11 @@ module Jekyll
     # Returns false if the file was not modified since last time (no-op).
     def write(dest)
       dest_path = destination(dest)
-      dest_dir = File.join(dest, @dir)
 
       return false if File.exist? dest_path and !modified?
       @@mtimes[path] = mtime
 
-      FileUtils.mkdir_p(dest_dir)
+      FileUtils.mkdir_p(File.dirname(dest_path))
       FileUtils.cp(path, dest_path)
 
       true
diff --git a/test/test_site.rb b/test/test_site.rb
index f18791de..d8d1057e 100644
--- a/test/test_site.rb
+++ b/test/test_site.rb
@@ -132,6 +132,39 @@ class TestSite < Test::Unit::TestCase
       assert_equal includes, @site.filter_entries(excludes + includes)
     end
     
+    context 'with orphaned files in destination' do
+      setup do
+        clear_dest
+        @site.process
+        # generate some orphaned files:
+        # hidden file
+        File.open(dest_dir('.htpasswd'), 'w')
+        # single file
+        File.open(dest_dir('obsolete.html'), 'w')
+        # single file in sub directory
+        FileUtils.mkdir(dest_dir('qux'))
+        File.open(dest_dir('qux/obsolete.html'), 'w')
+        # empty directory
+        FileUtils.mkdir(dest_dir('quux'))
+      end
+      
+      teardown do
+        FileUtils.rm_f(dest_dir('.htpasswd'))
+        FileUtils.rm_f(dest_dir('obsolete.html'))
+        FileUtils.rm_rf(dest_dir('qux'))
+        FileUtils.rm_f(dest_dir('quux'))
+      end
+      
+      should 'remove orphaned files in destination' do
+        @site.process
+        assert !File.exist?(dest_dir('.htpasswd'))
+        assert !File.exist?(dest_dir('obsolete.html'))
+        assert !File.exist?(dest_dir('qux'))
+        assert !File.exist?(dest_dir('quux'))
+      end
+
+    end
+    
     context 'with an invalid markdown processor in the configuration' do
       should 'not throw an error at initialization time' do
         bad_processor = 'not a processor name'