diff --git a/.github/workflows/macos.yml b/.github/workflows/macos.yml
index 4c98c320..5ce4b432 100644
--- a/.github/workflows/macos.yml
+++ b/.github/workflows/macos.yml
@@ -36,6 +36,7 @@ jobs:
           - TEST_EXPORT_STATIC
           - TEST_EXPORT_SHARED
           - OPENSSL_1_1
+          - BREW_AUTODETECT_OPENSSL
 
     steps:
       - uses: actions/checkout@v2.0.0
@@ -52,7 +53,10 @@ jobs:
       - name: Build And Test
         shell: bash
         run: |
-          if [ "${{ matrix.EVENT_MATRIX }}" == "OPENSSL_1_1" ]; then
+          if [ "${{ matrix.EVENT_MATRIX }}" == "BREW_AUTODETECT_OPENSSL" ]; then
+            # use autodetection via brew
+            :
+          elif [ "${{ matrix.EVENT_MATRIX }}" == "OPENSSL_1_1" ]; then
             export OPENSSL_ROOT_DIR=/usr/local/opt/openssl@1.1
           else
             export OPENSSL_ROOT_DIR=/usr/local/opt/openssl
@@ -121,6 +125,7 @@ jobs:
           - DISABLE_DEBUG_MODE
           - DISABLE_MM_REPLACEMENT
           - OPENSSL_1_1
+          - BREW_AUTODETECT_OPENSSL
 
     steps:
       - uses: actions/checkout@v2.0.0
@@ -137,7 +142,10 @@ jobs:
       - name: Build And Test
         shell: bash
         run: |
-          if [ "${{ matrix.EVENT_MATRIX }}" == "OPENSSL_1_1" ]; then
+          if [ "${{ matrix.EVENT_MATRIX }}" == "BREW_AUTODETECT_OPENSSL" ]; then
+            # use autodetection via brew
+            :
+          elif [ "${{ matrix.EVENT_MATRIX }}" == "OPENSSL_1_1" ]; then
             export PKG_CONFIG_PATH="/usr/local/opt/openssl@1.1/lib/pkgconfig:$PKG_CONFIG_PATH"
           else
             export PKG_CONFIG_PATH="/usr/local/opt/openssl/lib/pkgconfig:$PKG_CONFIG_PATH"
diff --git a/CMakeLists.txt b/CMakeLists.txt
index 0b188861..6d7da58c 100644
--- a/CMakeLists.txt
+++ b/CMakeLists.txt
@@ -238,6 +238,11 @@ else()
     message(FATAL_ERROR "${EVENT_LIBRARY_TYPE} is not supported")
 endif()
 
+# brew support
+if (APPLE)
+    find_program(BREW brew)
+endif()
+
 if (${MSVC})
     set(msvc_static_runtime OFF)
     if ("${EVENT_LIBRARY_TYPE}" STREQUAL "STATIC")
@@ -881,6 +886,20 @@ if(EVENT__HAVE_EVENT_PORTS)
 endif()
 
 if (NOT EVENT__DISABLE_OPENSSL)
+    # only if OPENSSL_ROOT_DIR is not set yet
+    if (BREW AND NOT OPENSSL_ROOT_DIR AND NOT "$ENV{OPENSSL_ROOT_DIR}")
+        execute_process(COMMAND ${BREW} --prefix openssl
+            OUTPUT_VARIABLE BREW_OPENSSL_PREFIX
+            RESULT_VARIABLE BREW_OPENSSL_RESULT
+            ERROR_QUIET
+            OUTPUT_STRIP_TRAILING_WHITESPACE
+        )
+        if (BREW_OPENSSL_RESULT EQUAL 0)
+            message(STATUS "Set OPENSSL_ROOT_DIR=${BREW_OPENSSL_PREFIX} (from brew)")
+            set(OPENSSL_ROOT_DIR "${BREW_OPENSSL_PREFIX}" CACHE PATH "")
+        endif()
+    endif()
+
     find_package(OpenSSL REQUIRED)
 
     set(EVENT__HAVE_OPENSSL 1)
diff --git a/m4/libevent_openssl.m4 b/m4/libevent_openssl.m4
index a5ea6762..b95d2449 100644
--- a/m4/libevent_openssl.m4
+++ b/m4/libevent_openssl.m4
@@ -3,6 +3,33 @@ dnl OpenSSL support
 AC_DEFUN([LIBEVENT_OPENSSL], [
 AC_REQUIRE([NTP_PKG_CONFIG])dnl
 
+case "$host_os" in
+    darwin*)
+    dnl when compiling for Darwin, attempt to find OpenSSL using brew.
+    dnl We append the location given by brew to PKG_CONFIG_PATH path
+    dnl and then export it, so that it can be used in detection below.
+    AC_CHECK_PROG([BREW],brew, brew)
+    if test x$BREW = xbrew; then
+        openssl_prefix=$($BREW --prefix openssl 2>/dev/null)
+        if test x$openssl_prefix != x; then
+            OPENSSL_LIBS=`$PKG_CONFIG --libs openssl 2>/dev/null`
+            case "$OPENSSL_LIBS" in
+             dnl only if openssl is not in PKG_CONFIG_PATH already
+             '')
+                if test x$PKG_CONFIG_PATH != x; then
+                    PKG_CONFIG_PATH="$PKG_CONFIG_PATH:"
+                fi
+                OPENSSL_PKG_CONFIG="$openssl_prefix/lib/pkgconfig"
+                PKG_CONFIG_PATH="$PKG_CONFIG_PATH$OPENSSL_PKG_CONFIG"
+                export PKG_CONFIG_PATH
+                AC_MSG_NOTICE([PKG_CONFIG_PATH has been set to $PKG_CONFIG_PATH (added openssl from brew)])
+                ;;
+            esac
+        fi
+    fi
+    ;;
+esac
+
 case "$enable_openssl" in
  yes)
     have_openssl=no
@@ -27,7 +54,7 @@ case "$enable_openssl" in
 	LIBS=""
 	OPENSSL_LIBS=""
 	for lib in crypto eay32; do
-		# clear cache
+		dnl clear cache
 		unset ac_cv_search_SSL_new
 		AC_SEARCH_LIBS([SSL_new], [ssl ssl32],
 		    [have_openssl=yes
@@ -47,15 +74,15 @@ case "$enable_openssl" in
     AC_SUBST(OPENSSL_LIBS)
     case "$have_openssl" in
      yes)  AC_DEFINE(HAVE_OPENSSL, 1, [Define if the system has openssl]) ;;
-     *) AC_MSG_ERROR([openssl is a must but can not be found. You should add the \
-directory containing `openssl.pc' to the `PKG_CONFIG_PATH' environment variable, \
-or set `CFLAGS' and `LDFLAGS' directly for openssl, or use `--disable-openssl' \
-to disable support for openssl encryption])
+     *) AC_MSG_ERROR([OpenSSL could not be found. You should add the directory \
+     containing 'openssl.pc' to the 'PKG_CONFIG_PATH' environment variable, set \
+     'CFLAGS' and 'LDFLAGS' directly, or use '--disable-openssl' to disable \
+     support for OpenSSL encryption])
 	;;
     esac
     ;;
 esac
 
-# check if we have and should use openssl
+dnl check if we have and should use OpenSSL
 AM_CONDITIONAL(OPENSSL, [test "$enable_openssl" != "no" && test "$have_openssl" = "yes"])
 ])