diff --git a/spec/config_spec.cr b/spec/config_spec.cr
index a7fc35c..11aa6d3 100644
--- a/spec/config_spec.cr
+++ b/spec/config_spec.cr
@@ -29,7 +29,7 @@ describe "Config" do
     config = Kemal.config
     config.add_handler CustomTestHandler.new
     Kemal.config.setup
-    config.handlers.size.should eq(7)
+    config.handlers.size.should eq(8)
   end
 
   it "toggles the shutdown message" do
diff --git a/spec/head_request_handler_spec.cr b/spec/head_request_handler_spec.cr
new file mode 100644
index 0000000..dc53970
--- /dev/null
+++ b/spec/head_request_handler_spec.cr
@@ -0,0 +1,37 @@
+require "./spec_helper"
+
+describe "Kemal::HeadRequestHandler" do
+  it "implicitly handles GET endpoints, with Content-Length header" do
+    get "/" do
+      "hello"
+    end
+    request = HTTP::Request.new("HEAD", "/")
+    client_response = call_request_on_app(request)
+    client_response.body.should eq("")
+    client_response.headers["Content-Length"].should eq("5")
+  end
+
+  it "prefers explicit HEAD endpoint if specified" do
+    Kemal::RouteHandler::INSTANCE.add_route("HEAD", "/") { "hello" }
+    get "/" do
+      raise "shouldn't be called!"
+    end
+    request = HTTP::Request.new("HEAD", "/")
+    client_response = call_request_on_app(request)
+    client_response.body.should eq("")
+    client_response.headers["Content-Length"].should eq("5")
+  end
+
+  it "gives compressed Content-Length when gzip enabled" do
+    gzip true
+    get "/" do
+      "hello"
+    end
+    headers = HTTP::Headers{"Accept-Encoding" => "gzip"}
+    request = HTTP::Request.new("HEAD", "/", headers)
+    client_response = call_request_on_app(request)
+    client_response.body.should eq("")
+    client_response.headers["Content-Encoding"].should eq("gzip")
+    client_response.headers["Content-Length"].should eq("25")
+  end
+end
diff --git a/spec/helpers_spec.cr b/spec/helpers_spec.cr
index d22687b..ec587bb 100644
--- a/spec/helpers_spec.cr
+++ b/spec/helpers_spec.cr
@@ -13,7 +13,7 @@ describe "Macros" do
     it "adds a custom handler" do
       add_handler CustomTestHandler.new
       Kemal.config.setup
-      Kemal.config.handlers.size.should eq 7
+      Kemal.config.handlers.size.should eq 8
     end
   end
 
@@ -150,7 +150,7 @@ describe "Macros" do
     it "adds HTTP::CompressHandler to handlers" do
       gzip true
       Kemal.config.setup
-      Kemal.config.handlers[4].should be_a(HTTP::CompressHandler)
+      Kemal.config.handlers[5].should be_a(HTTP::CompressHandler)
     end
   end
 
diff --git a/src/kemal/config.cr b/src/kemal/config.cr
index 3716960..02065b4 100644
--- a/src/kemal/config.cr
+++ b/src/kemal/config.cr
@@ -103,6 +103,7 @@ module Kemal
       unless @default_handlers_setup && @router_included
         setup_init_handler
         setup_log_handler
+        setup_head_request_handler
         setup_error_handler
         setup_static_file_handler
         setup_custom_handlers
@@ -129,6 +130,11 @@ module Kemal
       @handler_position += 1
     end
 
+    private def setup_head_request_handler
+      HANDLERS.insert(@handler_position, Kemal::HeadRequestHandler::INSTANCE)
+      @handler_position += 1
+    end
+
     private def setup_error_handler
       if @always_rescue
         @error_handler ||= Kemal::ExceptionHandler.new
diff --git a/src/kemal/head_request_handler.cr b/src/kemal/head_request_handler.cr
new file mode 100644
index 0000000..8dfcf50
--- /dev/null
+++ b/src/kemal/head_request_handler.cr
@@ -0,0 +1,60 @@
+require "http/server/handler"
+
+module Kemal
+  class HeadRequestHandler
+    include HTTP::Handler
+
+    INSTANCE = new
+
+    private class NullIO < IO
+      @original_output : IO
+      @out_count : Int32
+      @response : HTTP::Server::Response
+
+      def initialize(@response)
+        @closed = false
+        @original_output = @response.output
+        @out_count = 0
+      end
+
+      def read(slice : Bytes)
+        raise NotImplementedError.new("read")
+      end
+
+      def write(slice : Bytes) : Nil
+        @out_count += slice.bytesize
+      end
+
+      def close : Nil
+        return if @closed
+        @closed = true
+
+        # Matching HTTP::Server::Response#close behavior:
+        # Conditionally determine based on status if the `content-length` header should be added automatically.
+        # See https://tools.ietf.org/html/rfc7230#section-3.3.2.
+        status = @response.status
+        set_content_length = !(status.not_modified? || status.no_content? || status.informational?)
+
+        if !@response.headers.has_key?("Content-Length") && set_content_length
+          @response.content_length = @out_count
+        end
+
+        @original_output.close
+      end
+
+      def closed? : Bool
+        @closed
+      end
+    end
+
+    def call(context) : Nil
+      if context.request.method == "HEAD"
+        # Capture and count bytes of response body generated on HEAD requests without actually sending the body back.
+        capture_io = NullIO.new(context.response)
+        context.response.output = capture_io
+      end
+
+      call_next(context)
+    end
+  end
+end
diff --git a/src/kemal/helpers/helpers.cr b/src/kemal/helpers/helpers.cr
index a829808..0be1a94 100644
--- a/src/kemal/helpers/helpers.cr
+++ b/src/kemal/helpers/helpers.cr
@@ -5,11 +5,12 @@
 require "mime"
 
 # Adds given `Kemal::Handler` to handlers chain.
-# There are 5 handlers by default and all the custom handlers
-# goes between the first 4 and the last `Kemal::RouteHandler`.
+# There are 6 handlers by default and all the custom handlers
+# goes between the first 5 and the last `Kemal::RouteHandler`.
 #
 # - `Kemal::InitHandler`
 # - `Kemal::LogHandler`
+# - `Kemal::HeadRequestHandler`
 # - `Kemal::ExceptionHandler`
 # - `Kemal::StaticFileHandler`
 # - Here goes custom handlers
diff --git a/src/kemal/route_handler.cr b/src/kemal/route_handler.cr
index 698c6fd..44c8c92 100644
--- a/src/kemal/route_handler.cr
+++ b/src/kemal/route_handler.cr
@@ -17,11 +17,9 @@ module Kemal
       process_request(context)
     end
 
-    # Adds a given route to routing tree. As an exception each `GET` route additionaly defines
-    # a corresponding `HEAD` route.
+    # Adds a given route to routing tree.
     def add_route(method : String, path : String, &handler : HTTP::Server::Context -> _)
       add_to_radix_tree method, path, Route.new(method, path, &handler)
-      add_to_radix_tree("HEAD", path, Route.new("HEAD", path) { }) if method == "GET"
     end
 
     # Looks up the route from the Radix::Tree for the first time and caches to improve performance.
@@ -34,6 +32,11 @@ module Kemal
 
       route = @routes.find(lookup_path)
 
+      if verb == "HEAD" && !route.found?
+        # On HEAD requests, implicitly fallback to running the GET handler.
+        route = @routes.find(radix_path("GET", path))
+      end
+
       if route.found?
         @cached_routes.clear if @cached_routes.size == CACHED_ROUTES_LIMIT
         @cached_routes[lookup_path] = route