diff --git a/middleman-core/features/directory_index.feature b/middleman-core/features/directory_index.feature
index f8c87a21..ddbd703f 100644
--- a/middleman-core/features/directory_index.feature
+++ b/middleman-core/features/directory_index.feature
@@ -9,6 +9,7 @@ Feature: Directory Index
       | a_folder/needs_index/index.html               |
       | leave_me_alone.html                           |
       | wildcard_leave_me_alone.html                  |
+      | regex_leave_me_alone2.html                    |
       | evil spaces/index.html                        |
       | regular/index.html                            |
       | .htaccess                                     |
@@ -21,12 +22,13 @@ Feature: Directory Index
       | a_folder/needs_index.html                     |
       | leave_me_alone/index.html                     |
       | wildcard_leave_me_alone/index.html            |
+      | regex_leave_me_alone2/index.html              |
     And the file "needs_index/index.html" should contain "Indexable"
     And the file "a_folder/needs_index/index.html" should contain "Indexable"
     And the file "leave_me_alone.html" should contain "Stay away"
     And the file "regular/index.html" should contain "Regular"
     And the file "evil spaces/index.html" should contain "Filled with Evil Spaces"
-    
+
   Scenario: Preview normal file
     Given the Server is running at "indexable-app"
     When I go to "/needs_index/"
diff --git a/middleman-core/fixtures/indexable-app/config.rb b/middleman-core/fixtures/indexable-app/config.rb
index fdccfcbb..17c25ecf 100644
--- a/middleman-core/fixtures/indexable-app/config.rb
+++ b/middleman-core/fixtures/indexable-app/config.rb
@@ -2,3 +2,4 @@ activate :directory_indexes
 page "/leave_me_alone.html", directory_index: false
 
 page "/wildcard*", directory_index: false
+page /regex_.*/, directory_index: false
diff --git a/middleman-core/fixtures/indexable-app/source/regex_leave_me_alone2.html b/middleman-core/fixtures/indexable-app/source/regex_leave_me_alone2.html
new file mode 100644
index 00000000..5ff5317a
--- /dev/null
+++ b/middleman-core/fixtures/indexable-app/source/regex_leave_me_alone2.html
@@ -0,0 +1 @@
+Stay away, wildcards!
diff --git a/middleman-core/lib/middleman-core/core_extensions/routing.rb b/middleman-core/lib/middleman-core/core_extensions/routing.rb
index db773d29..dcbea0ec 100644
--- a/middleman-core/lib/middleman-core/core_extensions/routing.rb
+++ b/middleman-core/lib/middleman-core/core_extensions/routing.rb
@@ -44,7 +44,7 @@ module Middleman
       # @option opts [Hash] locals Local variables for the template. These will be available when the template renders.
       # @option opts [Hash] data Extra metadata to add to the page. This is the same as frontmatter, though frontmatter will take precedence over metadata defined here. Available via {Resource#data}.
       # @return [void]
-      Contract String, Hash => Any
+      Contract Or[String, Regexp], Hash => Any
       def page(path, opts={})
         options = opts.dup