diff --git a/ports/readline-osx/CMakeLists.txt b/ports/readline-osx/CMakeLists.txt
new file mode 100644
index 00000000000000..adf35eefaf9c8d
--- /dev/null
+++ b/ports/readline-osx/CMakeLists.txt
@@ -0,0 +1,60 @@
+cmake_minimum_required(VERSION 3.0)
+project(readline C)
+
+add_definitions(-DREADLINE_LIBRARY)
+add_definitions(-DHAVE_CONFIG_H)
+
+if(BUILD_SHARED_LIBS)
+  add_definitions(-DBUILD_READLINE_DLL)
+else()
+  add_definitions(-DREADLINE_STATIC)
+endif()
+
+include_directories(
+  ${CMAKE_CURRENT_SOURCE_DIR} # thats where the config.h is located
+)
+
+add_library(
+  readline
+  readline.c
+  funmap.c
+  keymaps.c
+  vi_mode.c
+  parens.c
+  rltty.c
+  complete.c
+  bind.c
+  colors.c
+  isearch.c
+  display.c
+  signals.c
+  util.c
+  kill.c
+  undo.c
+  macro.c
+  input.c
+  callback.c
+  terminal.c
+  xmalloc.c
+  history.c
+  histsearch.c
+  histexpand.c
+  histfile.c
+  nls.c
+  parse-colors.c
+  search.c
+  shell.c
+  savestring.c
+  tilde.c
+  text.c
+  misc.c
+  compat.c
+  mbutil.c
+  xfree.c
+  support/wcwidth.c)
+
+install(
+  TARGETS readline
+  RUNTIME DESTINATION bin
+  LIBRARY DESTINATION lib
+  ARCHIVE DESTINATION lib)
diff --git a/ports/readline-osx/config.h b/ports/readline-osx/config.h
new file mode 100644
index 00000000000000..b9cb89ca2dd924
--- /dev/null
+++ b/ports/readline-osx/config.h
@@ -0,0 +1,303 @@
+/* config.h.  Generated from config.h.in by configure.  */
+/* config.h.in.  Maintained by hand. */
+
+/* Template definitions for autoconf */
+#define __EXTENSIONS__ 1
+#define _ALL_SOURCE 1
+#define _GNU_SOURCE 1
+/* #undef _POSIX_SOURCE */
+/* #undef _POSIX_1_SOURCE */
+#define _POSIX_PTHREAD_SEMANTICS 1
+#define _TANDEM_SOURCE 1
+/* #undef _MINIX */
+
+/* Define NO_MULTIBYTE_SUPPORT to not compile in support for multibyte
+   characters, even if the OS supports them. */
+/* #undef NO_MULTIBYTE_SUPPORT */
+
+/* #undef _FILE_OFFSET_BITS */
+
+/* Define as the return type of signal handlers (int or void).  */
+#define RETSIGTYPE void
+
+#define VOID_SIGHANDLER 1
+
+/* Characteristics of the compiler. */
+/* #undef sig_atomic_t */
+
+/* #undef size_t */
+
+/* #undef ssize_t */
+
+/* #undef const */
+
+/* #undef volatile */
+
+#define PROTOTYPES 1
+#define __PROTOTYPES 1
+
+/* #undef __CHAR_UNSIGNED__ */
+
+/* Define if the `S_IS*' macros in <sys/stat.h> do not work properly.  */
+/* #undef STAT_MACROS_BROKEN */
+
+/* Define if you have the chown function. */
+#define HAVE_CHOWN 1
+
+/* Define if you have the fcntl function. */
+#define HAVE_FCNTL 1
+
+/* Define if you have the fnmatch function. */
+#define HAVE_FNMATCH 1
+
+/* Define if you have the getpwent function. */
+#define HAVE_GETPWENT 1
+
+/* Define if you have the getpwnam function. */
+#define HAVE_GETPWNAM 1
+
+/* Define if you have the getpwuid function. */
+#define HAVE_GETPWUID 1
+
+/* Define if you have the isascii function. */
+#define HAVE_ISASCII 1
+
+/* Define if you have the iswctype function.  */
+#define HAVE_ISWCTYPE 1
+
+/* Define if you have the iswlower function.  */
+#define HAVE_ISWLOWER 1
+
+/* Define if you have the iswupper function.  */
+#define HAVE_ISWUPPER 1
+
+/* Define if you have the isxdigit function. */
+#define HAVE_ISXDIGIT 1
+
+/* Define if you have the kill function. */
+#define HAVE_KILL 1
+
+/* Define if you have the lstat function. */
+#define HAVE_LSTAT 1
+
+/* Define if you have the mbrlen function. */
+#define HAVE_MBRLEN 1
+
+/* Define if you have the mbrtowc function. */
+#define HAVE_MBRTOWC 1
+
+/* Define if you have the mbsrtowcs function. */
+#define HAVE_MBSRTOWCS 1
+
+/* Define if you have the memmove function. */
+#define HAVE_MEMMOVE 1
+
+/* Define if you have the pselect function.  */
+#define HAVE_PSELECT 1
+
+/* Define if you have the putenv function.  */
+#define HAVE_PUTENV 1
+
+/* Define if you have the readlink function.  */
+#define HAVE_READLINK 1
+
+/* Define if you have the select function.  */
+#define HAVE_SELECT 1
+
+/* Define if you have the setenv function.  */
+#define HAVE_SETENV 1
+
+/* Define if you have the setlocale function. */
+#define HAVE_SETLOCALE 1
+
+/* Define if you have the strcasecmp function.  */
+#define HAVE_STRCASECMP 1
+
+/* Define if you have the strcoll function.  */
+#define HAVE_STRCOLL 1
+
+/* #undef STRCOLL_BROKEN */
+
+/* Define if you have the strpbrk function.  */
+#define HAVE_STRPBRK 1
+
+/* Define if you have the tcgetattr function.  */
+#define HAVE_TCGETATTR 1
+
+/* Define if you have the towlower function.  */
+#define HAVE_TOWLOWER 1
+
+/* Define if you have the towupper function.  */
+#define HAVE_TOWUPPER 1
+
+/* Define if you have the vsnprintf function.  */
+#define HAVE_VSNPRINTF 1
+
+/* Define if you have the wcrtomb function.  */
+#define HAVE_WCRTOMB 1
+
+/* Define if you have the wcscoll function.  */
+#define HAVE_WCSCOLL 1
+
+/* Define if you have the wctype function.  */
+#define HAVE_WCTYPE 1
+
+/* Define if you have the wcwidth function.  */
+#define HAVE_WCWIDTH 1
+
+/* and whether it works */
+/* #undef WCWIDTH_BROKEN */
+
+#define STDC_HEADERS 1
+
+/* Define if you have the <dirent.h> header file.  */
+#define HAVE_DIRENT_H 1
+
+/* Define if you have the <fcntl.h> header file.  */
+#define HAVE_FCNTL_H 1
+
+/* Define if you have the <langinfo.h> header file.  */
+#define HAVE_LANGINFO_H 1
+
+/* Define if you have the <libaudit.h> header file.  */
+/* #undef HAVE_LIBAUDIT_H */
+
+/* Define if you have the <limits.h> header file.  */
+#define HAVE_LIMITS_H 1
+
+/* Define if you have the <locale.h> header file.  */
+#define HAVE_LOCALE_H 1
+
+/* Define if you have the <memory.h> header file.  */
+#define HAVE_MEMORY_H 1
+
+/* Define if you have the <ndir.h> header file.  */
+/* #undef HAVE_NDIR_H */
+
+/* Define if you have the <ncurses/termcap.h> header file.  */
+/* #undef HAVE_NCURSES_TERMCAP_H */
+
+/* Define if you have the <pwd.h> header file.  */
+#define HAVE_PWD_H 1
+
+/* Define if you have the <stdarg.h> header file.  */
+#define HAVE_STDARG_H 1
+
+/* Define if you have the <stdbool.h> header file.  */
+#define HAVE_STDBOOL_H 1
+
+/* Define if you have the <stdlib.h> header file.  */
+#define HAVE_STDLIB_H 1
+
+/* Define if you have the <string.h> header file.  */
+#define HAVE_STRING_H 1
+
+/* Define if you have the <strings.h> header file.  */
+#define HAVE_STRINGS_H 1
+
+/* Define if you have the <sys/dir.h> header file.  */
+/* #undef HAVE_SYS_DIR_H */
+
+/* Define if you have the <sys/file.h> header file.  */
+#define HAVE_SYS_FILE_H 1
+
+/* Define if you have the <sys/ioctl.h> header file.  */
+#define HAVE_SYS_IOCTL_H 1
+
+/* Define if you have the <sys/ndir.h> header file.  */
+/* #undef HAVE_SYS_NDIR_H */
+
+/* Define if you have the <sys/pte.h> header file.  */
+/* #undef HAVE_SYS_PTE_H */
+
+/* Define if you have the <sys/ptem.h> header file.  */
+/* #undef HAVE_SYS_PTEM_H */
+
+/* Define if you have the <sys/select.h> header file.  */
+#define HAVE_SYS_SELECT_H 1
+
+/* Define if you have the <sys/stream.h> header file.  */
+/* #undef HAVE_SYS_STREAM_H */
+
+/* Define if you have the <termcap.h> header file.  */
+#define HAVE_TERMCAP_H 1
+
+/* Define if you have the <termio.h> header file.  */
+/* #undef HAVE_TERMIO_H */
+
+/* Define if you have the <termios.h> header file.  */
+#define HAVE_TERMIOS_H 1
+
+/* Define if you have the <unistd.h> header file.  */
+#define HAVE_UNISTD_H 1
+
+/* Define if you have the <varargs.h> header file.  */
+/* #undef HAVE_VARARGS_H */
+
+/* Define if you have the <wchar.h> header file.  */
+#define HAVE_WCHAR_H 1
+
+/* Define if you have the <wctype.h> header file.  */
+#define HAVE_WCTYPE_H 1
+
+#define HAVE_MBSTATE_T 1
+
+/* Define if you have wchar_t in <wctype.h>. */
+#define HAVE_WCHAR_T 1
+
+/* Define if you have wctype_t in <wctype.h>. */
+#define HAVE_WCTYPE_T 1
+
+/* Define if you have wint_t in <wctype.h>. */  
+#define HAVE_WINT_T 1
+
+/* Define if you have <langinfo.h> and nl_langinfo(CODESET). */
+#define HAVE_LANGINFO_CODESET 1
+
+/* Define if you have <linux/audit.h> and it defines AUDIT_USER_TTY */
+#define HAVE_DECL_AUDIT_USER_TTY 0
+
+/* Definitions pulled in from aclocal.m4. */
+#define VOID_SIGHANDLER 1
+
+/* #undef GWINSZ_IN_SYS_IOCTL */
+
+#define STRUCT_WINSIZE_IN_SYS_IOCTL 1
+
+/* #undef STRUCT_WINSIZE_IN_TERMIOS */
+
+#define TIOCSTAT_IN_SYS_IOCTL 1
+
+#define FIONREAD_IN_SYS_IOCTL 1
+
+/* #undef SPEED_T_IN_SYS_TYPES */
+
+#define HAVE_GETPW_DECLS 1
+
+#define HAVE_STRUCT_DIRENT_D_INO 1
+
+#define HAVE_STRUCT_DIRENT_D_FILENO 1
+
+/* #undef HAVE_STRUCT_DIRENT_D_NAMLEN */
+
+/* #undef HAVE_BSD_SIGNALS */
+
+#define HAVE_POSIX_SIGNALS 1
+
+/* #undef HAVE_USG_SIGHOLD */
+
+/* #undef MUST_REINSTALL_SIGHANDLERS */
+
+#define HAVE_POSIX_SIGSETJMP 1
+
+#define CTYPE_NON_ASCII 1
+
+/* modify settings or make new ones based on what autoconf tells us. */
+
+/* Ultrix botches type-ahead when switching from canonical to
+   non-canonical mode, at least through version 4.3 */
+#if !defined (HAVE_TERMIOS_H) || !defined (HAVE_TCGETATTR) || defined (ultrix)
+#  define TERMIOS_MISSING
+#endif
+
+/* VARARGS defines moved to rlstdc.h */
diff --git a/ports/readline-osx/portfile.cmake b/ports/readline-osx/portfile.cmake
new file mode 100644
index 00000000000000..f903ad071dde24
--- /dev/null
+++ b/ports/readline-osx/portfile.cmake
@@ -0,0 +1,26 @@
+vcpkg_download_distfile(
+  ARCHIVE
+  URLS https://ftp.gnu.org/gnu/readline/readline-8.1.tar.gz
+  FILENAME readline-8.1.tar.gz
+  SHA512 27790d0461da3093a7fee6e89a51dcab5dc61928ec42e9228ab36493b17220641d5e481ea3d8fee5ee0044c70bf960f55c7d3f1a704cf6b9c42e5c269b797e00
+)
+
+vcpkg_extract_source_archive(SOURCE_PATH ARCHIVE "${ARCHIVE}")
+
+file(
+  COPY "${CMAKE_CURRENT_LIST_DIR}/CMakeLists.txt"
+  DESTINATION "${SOURCE_PATH}")
+file(COPY "${CMAKE_CURRENT_LIST_DIR}/config.h" DESTINATION "${SOURCE_PATH}")
+
+vcpkg_cmake_configure(SOURCE_PATH "${SOURCE_PATH}")
+
+vcpkg_cmake_install()
+
+file(MAKE_DIRECTORY "${CURRENT_PACKAGES_DIR}/include/readline")
+file(GLOB headers "${SOURCE_PATH}/*.h")
+file(COPY ${headers} DESTINATION "${CURRENT_PACKAGES_DIR}/include/readline")
+
+file(
+  INSTALL "${SOURCE_PATH}/COPYING"
+  DESTINATION "${CURRENT_PACKAGES_DIR}/share/${PORT}"
+  RENAME copyright)
diff --git a/ports/readline-osx/vcpkg.json b/ports/readline-osx/vcpkg.json
new file mode 100644
index 00000000000000..4ea10360bd75ed
--- /dev/null
+++ b/ports/readline-osx/vcpkg.json
@@ -0,0 +1,16 @@
+{
+  "name": "readline-osx",
+  "version": "8.1",
+  "description": "Implementation of readline for Mac OS",
+  "supports": "osx",
+  "dependencies": [
+    {
+      "name": "vcpkg-cmake",
+      "host": true
+    },
+    {
+      "name": "vcpkg-cmake-config",
+      "host": true
+    }
+  ]
+}
diff --git a/ports/readline/vcpkg.json b/ports/readline/vcpkg.json
index 7dba01a74c9b3a..5ba03cd6c7b142 100644
--- a/ports/readline/vcpkg.json
+++ b/ports/readline/vcpkg.json
@@ -1,10 +1,14 @@
 {
   "name": "readline",
   "version-string": "0",
-  "port-version": 1,
+  "port-version": 2,
   "description": "GNU readline and history libraries",
   "supports": "!uwp",
   "dependencies": [
+    {
+      "name": "readline-osx",
+      "platform": "osx"
+    },
     {
       "name": "readline-win32",
       "platform": "windows"
diff --git a/versions/baseline.json b/versions/baseline.json
index 5756686397cf13..2c0cffbf339b48 100644
--- a/versions/baseline.json
+++ b/versions/baseline.json
@@ -5970,7 +5970,11 @@
     },
     "readline": {
       "baseline": "0",
-      "port-version": 1
+      "port-version": 2
+    },
+    "readline-osx": {
+      "baseline": "8.1",
+      "port-version": 0
     },
     "readline-win32": {
       "baseline": "5.0",
diff --git a/versions/r-/readline-osx.json b/versions/r-/readline-osx.json
new file mode 100644
index 00000000000000..5e7dca323bf46b
--- /dev/null
+++ b/versions/r-/readline-osx.json
@@ -0,0 +1,9 @@
+{
+  "versions": [
+    {
+      "git-tree": "5b4b6fabb77d9f67ee0a4dcc7981040d9177caed",
+      "version": "8.1",
+      "port-version": 0
+    }
+  ]
+}
diff --git a/versions/r-/readline.json b/versions/r-/readline.json
index 672cc6f0c6b34a..6a22adcaeb6c59 100644
--- a/versions/r-/readline.json
+++ b/versions/r-/readline.json
@@ -1,5 +1,10 @@
 {
   "versions": [
+    {
+      "git-tree": "b5c6800bc0cf924ec6bdbe627c9460839774f998",
+      "version-string": "0",
+      "port-version": 2
+    },
     {
       "git-tree": "1e0a62b3927f5b41e7861093dba7d2e2aa4de0b2",
       "version-string": "0",