diff --git a/website/www/config.rb b/website/www/config.rb
index 418cff3f0..fa0afaa3c 100644
--- a/website/www/config.rb
+++ b/website/www/config.rb
@@ -1,5 +1,13 @@
+require File.expand_path("../helpers/download_helpers", __FILE__)
+
 page "/blog_feed.xml", layout: false
 
+# Archived download pages
+$vagrant_versions.each do |version|
+  proxy "/download-archive/v#{version}.html", "/download-archive-single.html",
+    locals: { version: version }, ignore: true
+end
+
 set :css_dir, 'stylesheets'
 set :js_dir, 'javascripts'
 set :images_dir, 'images'
diff --git a/website/www/helpers/download_helpers.rb b/website/www/helpers/download_helpers.rb
index 993e34aec..0bf4ea6ca 100644
--- a/website/www/helpers/download_helpers.rb
+++ b/website/www/helpers/download_helpers.rb
@@ -10,8 +10,12 @@ $vagrant_os_mappings = {
   ".rpm" => "rpm",
 }
 
+$vagrant_os_order  = ["darwin", "windows", "debian", "rpm"]
+$vagrant_downloads = {}
+$vagrant_versions  = []
+
 if ENV["VAGRANT_VERSION"]
-  puts "Finding downloads for Vagrant: #{ENV["VAGRANT_VERSION"]}"
+  puts "Finding downloads for Vagrant"
   raise "BINTRAY_API_KEY must be set." if !ENV["BINTRAY_API_KEY"]
   http = Net::HTTP.new("dl.bintray.com", 80)
   req = Net::HTTP::Get.new("/mitchellh/vagrant")
@@ -21,26 +25,23 @@ if ENV["VAGRANT_VERSION"]
   response.body.split("\n").each do |line|
     next if line !~ /\/mitchellh\/vagrant\/(.+?)'/
     filename = $1.to_s
-    $vagrant_os_mappings.each do |suffix, os|
-      if !filename.include?(ENV["VAGRANT_VERSION"])
-        next
-      end
 
+    # Ignore any files that don't appear to have a version in it
+    next if filename !~ /[-_]?(\d+\.\d+\.\d+[^-_.]*)/
+    version = Gem::Version.new($1.to_s)
+    $vagrant_downloads[version] ||= {}
+
+    $vagrant_os_mappings.each do |suffix, os|
       if filename.end_with?(suffix)
-        $vagrant_files[os] ||= []
-        $vagrant_files[os] << filename
+        $vagrant_downloads[version][os] ||= []
+        $vagrant_downloads[version][os] << filename
       end
     end
   end
 
-  $vagrant_os = $vagrant_files.keys
-  $vagrant_files.each do |key, value|
-    value.sort!
-
-    puts "Downloads for #{key}:"
-    value.each do |file|
-      puts "  -- File: #{file}"
-    end
+  $vagrant_versions = $vagrant_downloads.keys.sort.reverse
+  $vagrant_versions.each do |v|
+    puts "- Version #{v} found"
   end
 else
   puts "Not generating downloads."
@@ -76,6 +77,6 @@ module DownloadHelpers
   end
 
   def latest_version
-    ENV["VAGRANT_VERSION"]
+    $vagrant_versions.first
   end
 end
diff --git a/website/www/source/download-archive-single.html.erb b/website/www/source/download-archive-single.html.erb
new file mode 100644
index 000000000..2547ccedc
--- /dev/null
+++ b/website/www/source/download-archive-single.html.erb
@@ -0,0 +1,51 @@
+---
+layout: "inner"
+sidebar_current: "downloads"
+sidebar_template: "downloads"
+sidebar_title: "Download"
+page_title: "Download Old Vagrant Version"
+---
+
+<h2>Old Vagrant Version: <%= version %></h2>
+
+<div class="alert alert-block alert-info">
+This is the downloads page for an <em>old</em> version of Vagrant.
+The latest version of Vagrant can always be found on the
+<a href="/downloads.html">main downloads page</a>.
+</div>
+
+<div class="downloads">
+<div class="description">
+<p>
+You can find the SHA256 checksums for this version of Vagrant
+<a href="https://dl.bintray.com/mitchellh/vagrant/<%= version %>_SHA256SUMS?direct">here</a>.
+</p>
+</div>
+
+<% $vagrant_os_order.each do |os| %>
+	<% downloads = $vagrant_downloads[version] %>
+	<% if downloads[os] && !downloads[os].empty? %>
+	<div class="row">
+	<div class="span8 download">
+		<div class="icon pull-left"><%= image_tag "/images/icons/icon_#{os}.png" %></div>
+		<div class="details">
+			<h2 class="os-name"><%= download_os_human(os) %></h2>
+			<ul>
+				<% downloads[os].each do |file| %>
+					<li><a href="<%= download_url(file) %>"><%= download_arch(file) %></a></li>
+			<% end %>
+			</ul>
+			<div class="clearfix"></div>
+		</div>
+	</div>
+	</div>
+	<% end %>
+<% end %>
+
+	<div class="poweredby">
+		<a href='http://www.bintray.com'>
+			<img src='http://www.bintray.com/docs/images/poweredByBintray_ColorTransparent.png'>
+		</a>
+	</div>
+</div>
+
diff --git a/website/www/source/downloads-archive.html.erb b/website/www/source/downloads-archive.html.erb
index b63f6bc5c..54359b64e 100644
--- a/website/www/source/downloads-archive.html.erb
+++ b/website/www/source/downloads-archive.html.erb
@@ -9,11 +9,13 @@ page_title: "Download Old Versions of Vagrant"
 <h2>Old Versions</h2>
 
 <p>
-Old versions of Vagrant can currently be found at the old downloads
-website here: <a href="http://downloads.vagrantup.com/">http://downloads.vagrantup.com/</a>
+This webpage lists the older versions of Vagrant that are available for
+download. Some even older versions are available from the
+<a href="http://downloads.vagrantup.com/">legacy downloads page</a>.
 </p>
 
-<p>
-In the future, old versions will be transitioned to the new download
-system, so please do not rely on the URLs at that web page.
-</p>
+<ul>
+	<% $vagrant_versions.each do |version| %>
+		<li><a href="/download-archive/v<%= version.to_s %>.html"><%= version.to_s %></a></li>
+	<% end %>
+</ul>
diff --git a/website/www/source/downloads.html.erb b/website/www/source/downloads.html.erb
index 0c5e879bd..c1b02b08f 100644
--- a/website/www/source/downloads.html.erb
+++ b/website/www/source/downloads.html.erb
@@ -18,14 +18,17 @@ for packages <a href="https://dl.bintray.com/mitchellh/vagrant/<%= latest_versio
 </p>
 </div>
 
-<% $vagrant_os.each do |os| %>
+<% if latest_version %>
+<% $vagrant_os_order.each do |os| %>
+	<% downloads = $vagrant_downloads[latest_version] %>
+	<% if downloads[os] && !downloads[os].empty? %>
 	<div class="row">
 	<div class="span8 download">
 		<div class="icon pull-left"><%= image_tag "/images/icons/icon_#{os}.png" %></div>
 		<div class="details">
 			<h2 class="os-name"><%= download_os_human(os) %></h2>
 			<ul>
-				<% $vagrant_files[os].each do |file| %>
+				<% downloads[os].each do |file| %>
 					<li><a href="<%= download_url(file) %>"><%= download_arch(file) %></a></li>
 			<% end %>
 			</ul>
@@ -33,6 +36,8 @@ for packages <a href="https://dl.bintray.com/mitchellh/vagrant/<%= latest_versio
 		</div>
 	</div>
 	</div>
+	<% end %>
+<% end %>
 <% end %>
 
 	<div class="poweredby">