diff --git a/lib/vagrant/env.rb b/lib/vagrant/env.rb
index 0c70ec2ce..83fb4d5ff 100644
--- a/lib/vagrant/env.rb
+++ b/lib/vagrant/env.rb
@@ -89,7 +89,10 @@ module Vagrant
       def load_root_path!(path=nil)
         path ||= Pathname.new(Dir.pwd)
 
-        return false if path.to_s == '/'
+        # Stop if we're at the root. 2nd regex matches windows drives
+        # such as C:. and Z:. Portability of this check will need to be
+        # researched.
+        return false if path.to_s == '/' || path.to_s =~ /^[A-Z]:\.$/
 
         file = "#{path}/#{ROOTFILE_NAME}"
         if File.exist?(file)
diff --git a/test/vagrant/env_test.rb b/test/vagrant/env_test.rb
index 7766f5f6d..75b2da9a6 100644
--- a/test/vagrant/env_test.rb
+++ b/test/vagrant/env_test.rb
@@ -218,11 +218,16 @@ class EnvTest < Test::Unit::TestCase
       assert !Vagrant::Env.load_root_path!(paths.first)
     end
 
-    should "should return false if not found" do
+    should "return false if not found" do
       path = Pathname.new("/")
       assert !Vagrant::Env.load_root_path!(path)
     end
 
+    should "return false if not found on windows-style root" do
+      path = Pathname.new("C:.")
+      assert !Vagrant::Env.load_root_path!(path)
+    end
+
     should "should set the path for the rootfile" do
       path = "/foo"
       File.expects(:exist?).with("#{path}/#{Vagrant::Env::ROOTFILE_NAME}").returns(true)