diff --git Mk/Uses/python.mk Mk/Uses/python.mk
index fcaf479d8076..5906013fd3cb 100644
--- Mk/Uses/python.mk
+++ Mk/Uses/python.mk
@@ -554,10 +554,16 @@ UNIQUE_FIND_SUFFIX_MAN_FILES+=	${_UNIQUE_FIND_SUFFIX_FILES} | \
 
 _CURRENTPORT:=	${PKGNAMEPREFIX}${PORTNAME}${PKGNAMESUFFIX}
 .if defined(_PYTHON_FEATURE_DISTUTILS) && \
-	${_CURRENTPORT} != ${PYTHON_PKGNAMEPREFIX}setuptools
+	${_CURRENTPORT} != ${PYTHON_PKGNAMEPREFIX}setuptools &&\
+	${_CURRENTPORT} != ${PYTHON_PKGNAMEPREFIX}setuptools44
+.if ${PYTHON_VER} == 2.7
+BUILD_DEPENDS+=		${PYTHON_PKGNAMEPREFIX}setuptools44>0:devel/py-setuptools44@${PY_FLAVOR}
+RUN_DEPENDS+=		${PYTHON_PKGNAMEPREFIX}setuptools44>0:devel/py-setuptools44@${PY_FLAVOR}
+.else
 BUILD_DEPENDS+=		${PYTHON_PKGNAMEPREFIX}setuptools>0:devel/py-setuptools@${PY_FLAVOR}
 RUN_DEPENDS+=		${PYTHON_PKGNAMEPREFIX}setuptools>0:devel/py-setuptools@${PY_FLAVOR}
 .endif
+.endif
 
 # distutils support
 PYSETUP?=		setup.py
diff --git devel/Makefile devel/Makefile
index 66f87ddf7391..8ac4e9abd371 100644
--- devel/Makefile
+++ devel/Makefile
@@ -5125,6 +5125,7 @@
     SUBDIR += py-setuptools
     SUBDIR += py-setuptools-git
     SUBDIR += py-setuptools-pkg
+    SUBDIR += py-setuptools44
     SUBDIR += py-setuptools_hg
     SUBDIR += py-setuptools_scm
     SUBDIR += py-setuptools_scm_git_archive
diff --git devel/py-setuptools/Makefile devel/py-setuptools/Makefile
index 759dbdc8cd6e..f41e53d59498 100644
--- devel/py-setuptools/Makefile
+++ devel/py-setuptools/Makefile
@@ -1,6 +1,5 @@
 PORTNAME=	setuptools
-PORTVERSION=	44.0.0
-PORTREVISION=	1
+PORTVERSION=	57.0.0
 CATEGORIES=	devel python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
@@ -15,7 +14,7 @@ COMMENT=	Python packages installer
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
-USES=		python:2.7+ zip
+USES=		python:3.6+
 USE_PYTHON=	allflavors autoplist concurrent distutils
 
 MAKE_ENV+=	SETUPTOOLS_DISABLE_VERSIONED_EASY_INSTALL_SCRIPT=1
diff --git devel/py-setuptools/distinfo devel/py-setuptools/distinfo
index 759bcc340fdd..98989e164334 100644
--- devel/py-setuptools/distinfo
+++ devel/py-setuptools/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1578923982
-SHA256 (python/setuptools-44.0.0.zip) = e5baf7723e5bb8382fc146e33032b241efc63314211a3a120aaa55d62d2bb008
-SIZE (python/setuptools-44.0.0.zip) = 858893
+TIMESTAMP = 1622043161
+SHA256 (python/setuptools-57.0.0.tar.gz) = 401cbf33a7bf817d08014d51560fc003b895c4cdc1a5b521ad2969e928a07535
+SIZE (python/setuptools-57.0.0.tar.gz) = 2144749
diff --git devel/py-setuptools44/Makefile devel/py-setuptools44/Makefile
new file mode 100644
index 000000000000..173d4c0ea6d7
--- /dev/null
+++ devel/py-setuptools44/Makefile
@@ -0,0 +1,49 @@
+PORTNAME=	setuptools
+PORTVERSION=	44.0.0
+PORTREVISION=	1
+CATEGORIES=	devel python
+MASTER_SITES=	CHEESESHOP
+PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
+PKGNAMESUFFIX=	44
+DIST_SUBDIR=	python
+
+# note: before committing to this port, contact portmgr to arrange for an
+# experimental ports run.  Untested commits may be backed out at portmgr's
+# discretion.
+MAINTAINER=	python@FreeBSD.org
+COMMENT=	Python packages installer
+
+LICENSE=	MIT
+LICENSE_FILE=	${WRKSRC}/LICENSE
+
+USES=		python:2.7 zip
+USE_PYTHON=	allflavors autoplist concurrent distutils
+
+MAKE_ENV+=	SETUPTOOLS_DISABLE_VERSIONED_EASY_INSTALL_SCRIPT=1
+NO_ARCH=	yes
+PYDISTUTILS_SETUP=	${PYSETUP}
+
+PLIST_FILES=	"@sample %%PYTHON_SITELIBDIR%%/easy-install.pth.dist %%PYTHON_SITELIBDIR%%/easy-install.pth"
+
+.include <bsd.port.pre.mk>
+
+.if ${FLAVOR} != ${FLAVORS:[1]}
+SUB_FILES+=	pkg-message
+SUB_LIST+=	PYTHON_VER=${PYTHON_VER}
+.endif
+
+# These create dependency loops in redports/poudriere, because setuptools
+# is currently an explicit BUILD & RUN dependency in Uses/python.mk.
+#TEST_DEPENDS=  ${PYTHON_PKGNAMEPREFIX}pytest>0:devel/py-pytest@${PY_FLAVOR}
+#.if ${PYTHON_REL} < 30300
+#TEST_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}mock>0:devel/py-mock@${PY_FLAVOR}
+#.endif
+# pkg install -y py36-pytest py36-mock py36-pytest-fixture-config py36-pytest-virtualenv py36-paver
+
+post-install:
+	${INSTALL_DATA} ${FILESDIR}/easy-install.pth.dist ${STAGEDIR}${PYTHON_SITELIBDIR}/
+
+do-test:
+	cd ${WRKSRC} && ${PYTHON_CMD} -m pytest -v -rs
+
+.include <bsd.port.post.mk>
diff --git devel/py-setuptools44/distinfo devel/py-setuptools44/distinfo
new file mode 100644
index 000000000000..759bcc340fdd
--- /dev/null
+++ devel/py-setuptools44/distinfo
@@ -0,0 +1,3 @@
+TIMESTAMP = 1578923982
+SHA256 (python/setuptools-44.0.0.zip) = e5baf7723e5bb8382fc146e33032b241efc63314211a3a120aaa55d62d2bb008
+SIZE (python/setuptools-44.0.0.zip) = 858893
diff --git devel/py-setuptools44/files/easy-install.pth.dist devel/py-setuptools44/files/easy-install.pth.dist
new file mode 100644
index 000000000000..e7ab88be464d
--- /dev/null
+++ devel/py-setuptools44/files/easy-install.pth.dist
@@ -0,0 +1,2 @@
+import sys; sys.__plen = len(sys.path)
+import sys; new=sys.path[sys.__plen:]; del sys.path[sys.__plen:]; p=getattr(sys,'__egginsert',0); sys.path[p:p]=new; sys.__egginsert = p+len(new)
diff --git devel/py-setuptools44/files/pkg-message.in devel/py-setuptools44/files/pkg-message.in
new file mode 100644
index 000000000000..2c33be99f2e5
--- /dev/null
+++ devel/py-setuptools44/files/pkg-message.in
@@ -0,0 +1,8 @@
+[
+{ type: install
+  message: <<EOM
+  Only %%PREFIX%%/bin/easy_install-%%PYTHON_VER%% script has been installed
+  since Python %%PYTHON_VER%% is not the default Python version.
+EOM
+}
+]
diff --git devel/py-setuptools44/pkg-descr devel/py-setuptools44/pkg-descr
new file mode 100644
index 000000000000..abcbbd10ceab
--- /dev/null
+++ devel/py-setuptools44/pkg-descr
@@ -0,0 +1,10 @@
+Setuptools is a fully-featured, actively-maintained, and stable library
+designed to facilitate packaging Python projects, where packaging includes:
+ - Python package and module definitions
+ - Distribution package metadata
+ - Test hooks
+ - Project installation
+ - Platform-specific details
+ - Python 3 support
+
+WWW: https://pypi.org/project/setuptools/