diff --git a/src/_pytest/config/__init__.py b/src/_pytest/config/__init__.py
index bd9e2883f..0df4ffa01 100644
--- a/src/_pytest/config/__init__.py
+++ b/src/_pytest/config/__init__.py
@@ -50,9 +50,11 @@ from _pytest.compat import final
 from _pytest.compat import importlib_metadata
 from _pytest.outcomes import fail
 from _pytest.outcomes import Skipped
+from _pytest.pathlib import absolutepath
 from _pytest.pathlib import bestrelpath
 from _pytest.pathlib import import_path
 from _pytest.pathlib import ImportMode
+from _pytest.pathlib import resolve_package_path
 from _pytest.store import Store
 from _pytest.warning_types import PytestConfigWarning
 
@@ -102,9 +104,7 @@ class ExitCode(enum.IntEnum):
 
 class ConftestImportFailure(Exception):
     def __init__(
-        self,
-        path: py.path.local,
-        excinfo: Tuple[Type[Exception], Exception, TracebackType],
+        self, path: Path, excinfo: Tuple[Type[Exception], Exception, TracebackType],
     ) -> None:
         super().__init__(path, excinfo)
         self.path = path
@@ -342,9 +342,9 @@ class PytestPluginManager(PluginManager):
         self._conftest_plugins: Set[types.ModuleType] = set()
 
         # State related to local conftest plugins.
-        self._dirpath2confmods: Dict[py.path.local, List[types.ModuleType]] = {}
+        self._dirpath2confmods: Dict[Path, List[types.ModuleType]] = {}
         self._conftestpath2mod: Dict[Path, types.ModuleType] = {}
-        self._confcutdir: Optional[py.path.local] = None
+        self._confcutdir: Optional[Path] = None
         self._noconftest = False
         self._duplicatepaths: Set[py.path.local] = set()
 
@@ -479,9 +479,9 @@ class PytestPluginManager(PluginManager):
         All builtin and 3rd party plugins will have been loaded, however, so
         common options will not confuse our logic here.
         """
-        current = py.path.local()
+        current = Path.cwd()
         self._confcutdir = (
-            current.join(namespace.confcutdir, abs=True)
+            absolutepath(current / namespace.confcutdir)
             if namespace.confcutdir
             else None
         )
@@ -495,7 +495,7 @@ class PytestPluginManager(PluginManager):
             i = path.find("::")
             if i != -1:
                 path = path[:i]
-            anchor = current.join(path, abs=1)
+            anchor = absolutepath(current / path)
             if anchor.exists():  # we found some file object
                 self._try_load_conftest(anchor, namespace.importmode)
                 foundanchor = True
@@ -503,24 +503,24 @@ class PytestPluginManager(PluginManager):
             self._try_load_conftest(current, namespace.importmode)
 
     def _try_load_conftest(
-        self, anchor: py.path.local, importmode: Union[str, ImportMode]
+        self, anchor: Path, importmode: Union[str, ImportMode]
     ) -> None:
         self._getconftestmodules(anchor, importmode)
         # let's also consider test* subdirs
-        if anchor.check(dir=1):
-            for x in anchor.listdir("test*"):
-                if x.check(dir=1):
+        if anchor.is_dir():
+            for x in anchor.glob("test*"):
+                if x.is_dir():
                     self._getconftestmodules(x, importmode)
 
     @lru_cache(maxsize=128)
     def _getconftestmodules(
-        self, path: py.path.local, importmode: Union[str, ImportMode],
+        self, path: Path, importmode: Union[str, ImportMode],
     ) -> List[types.ModuleType]:
         if self._noconftest:
             return []
 
-        if path.isfile():
-            directory = path.dirpath()
+        if path.is_file():
+            directory = path.parent
         else:
             directory = path
 
@@ -528,18 +528,18 @@ class PytestPluginManager(PluginManager):
         # and allow users to opt into looking into the rootdir parent
         # directories instead of requiring to specify confcutdir.
         clist = []
-        for parent in directory.parts():
-            if self._confcutdir and self._confcutdir.relto(parent):
+        for parent in reversed((directory, *directory.parents)):
+            if self._confcutdir and parent in self._confcutdir.parents:
                 continue
-            conftestpath = parent.join("conftest.py")
-            if conftestpath.isfile():
+            conftestpath = parent / "conftest.py"
+            if conftestpath.is_file():
                 mod = self._importconftest(conftestpath, importmode)
                 clist.append(mod)
         self._dirpath2confmods[directory] = clist
         return clist
 
     def _rget_with_confmod(
-        self, name: str, path: py.path.local, importmode: Union[str, ImportMode],
+        self, name: str, path: Path, importmode: Union[str, ImportMode],
     ) -> Tuple[types.ModuleType, Any]:
         modules = self._getconftestmodules(path, importmode)
         for mod in reversed(modules):
@@ -550,21 +550,21 @@ class PytestPluginManager(PluginManager):
         raise KeyError(name)
 
     def _importconftest(
-        self, conftestpath: py.path.local, importmode: Union[str, ImportMode],
+        self, conftestpath: Path, importmode: Union[str, ImportMode],
     ) -> types.ModuleType:
         # Use a resolved Path object as key to avoid loading the same conftest
         # twice with build systems that create build directories containing
         # symlinks to actual files.
         # Using Path().resolve() is better than py.path.realpath because
         # it resolves to the correct path/drive in case-insensitive file systems (#5792)
-        key = Path(str(conftestpath)).resolve()
+        key = conftestpath.resolve()
 
         with contextlib.suppress(KeyError):
             return self._conftestpath2mod[key]
 
-        pkgpath = conftestpath.pypkgpath()
+        pkgpath = resolve_package_path(conftestpath)
         if pkgpath is None:
-            _ensure_removed_sysmodule(conftestpath.purebasename)
+            _ensure_removed_sysmodule(conftestpath.stem)
 
         try:
             mod = import_path(conftestpath, mode=importmode)
@@ -577,10 +577,10 @@ class PytestPluginManager(PluginManager):
 
         self._conftest_plugins.add(mod)
         self._conftestpath2mod[key] = mod
-        dirpath = conftestpath.dirpath()
+        dirpath = conftestpath.parent
         if dirpath in self._dirpath2confmods:
             for path, mods in self._dirpath2confmods.items():
-                if path and path.relto(dirpath) or path == dirpath:
+                if path and dirpath in path.parents or path == dirpath:
                     assert mod not in mods
                     mods.append(mod)
         self.trace(f"loading conftestmodule {mod!r}")
@@ -588,7 +588,7 @@ class PytestPluginManager(PluginManager):
         return mod
 
     def _check_non_top_pytest_plugins(
-        self, mod: types.ModuleType, conftestpath: py.path.local,
+        self, mod: types.ModuleType, conftestpath: Path,
     ) -> None:
         if (
             hasattr(mod, "pytest_plugins")
@@ -1412,21 +1412,23 @@ class Config:
             assert type in [None, "string"]
             return value
 
-    def _getconftest_pathlist(
-        self, name: str, path: py.path.local
-    ) -> Optional[List[py.path.local]]:
+    def _getconftest_pathlist(self, name: str, path: Path) -> Optional[List[Path]]:
         try:
             mod, relroots = self.pluginmanager._rget_with_confmod(
                 name, path, self.getoption("importmode")
             )
         except KeyError:
             return None
-        modpath = py.path.local(mod.__file__).dirpath()
-        values: List[py.path.local] = []
+        modpath = Path(mod.__file__).parent
+        values: List[Path] = []
         for relroot in relroots:
-            if not isinstance(relroot, py.path.local):
+            if isinstance(relroot, Path):
+                pass
+            elif isinstance(relroot, py.path.local):
+                relroot = Path(relroot)
+            else:
                 relroot = relroot.replace("/", os.sep)
-                relroot = modpath.join(relroot, abs=True)
+                relroot = absolutepath(modpath / relroot)
             values.append(relroot)
         return values
 
diff --git a/src/_pytest/doctest.py b/src/_pytest/doctest.py
index 64e8f0e0e..d0b6b4c41 100644
--- a/src/_pytest/doctest.py
+++ b/src/_pytest/doctest.py
@@ -7,6 +7,7 @@ import traceback
 import types
 import warnings
 from contextlib import contextmanager
+from pathlib import Path
 from typing import Any
 from typing import Callable
 from typing import Dict
@@ -525,7 +526,7 @@ class DoctestModule(pytest.Module):
 
         if self.fspath.basename == "conftest.py":
             module = self.config.pluginmanager._importconftest(
-                self.fspath, self.config.getoption("importmode")
+                Path(self.fspath), self.config.getoption("importmode")
             )
         else:
             try:
diff --git a/src/_pytest/main.py b/src/_pytest/main.py
index 41a33d449..eab3c9afd 100644
--- a/src/_pytest/main.py
+++ b/src/_pytest/main.py
@@ -371,22 +371,23 @@ def _in_venv(path: py.path.local) -> bool:
 
 
 def pytest_ignore_collect(path: py.path.local, config: Config) -> Optional[bool]:
-    ignore_paths = config._getconftest_pathlist("collect_ignore", path=path.dirpath())
+    path_ = Path(path)
+    ignore_paths = config._getconftest_pathlist("collect_ignore", path=path_.parent)
     ignore_paths = ignore_paths or []
     excludeopt = config.getoption("ignore")
     if excludeopt:
-        ignore_paths.extend([py.path.local(x) for x in excludeopt])
+        ignore_paths.extend(absolutepath(x) for x in excludeopt)
 
-    if py.path.local(path) in ignore_paths:
+    if path_ in ignore_paths:
         return True
 
     ignore_globs = config._getconftest_pathlist(
-        "collect_ignore_glob", path=path.dirpath()
+        "collect_ignore_glob", path=path_.parent
     )
     ignore_globs = ignore_globs or []
     excludeglobopt = config.getoption("ignore_glob")
     if excludeglobopt:
-        ignore_globs.extend([py.path.local(x) for x in excludeglobopt])
+        ignore_globs.extend(absolutepath(x) for x in excludeglobopt)
 
     if any(fnmatch.fnmatch(str(path), str(glob)) for glob in ignore_globs):
         return True
@@ -512,12 +513,12 @@ class Session(nodes.FSCollector):
     def isinitpath(self, path: py.path.local) -> bool:
         return path in self._initialpaths
 
-    def gethookproxy(self, fspath: py.path.local):
+    def gethookproxy(self, fspath: "os.PathLike[str]"):
         # Check if we have the common case of running
         # hooks with all conftest.py files.
         pm = self.config.pluginmanager
         my_conftestmodules = pm._getconftestmodules(
-            fspath, self.config.getoption("importmode")
+            Path(fspath), self.config.getoption("importmode")
         )
         remove_mods = pm._conftest_plugins.difference(my_conftestmodules)
         if remove_mods:
@@ -668,8 +669,9 @@ class Session(nodes.FSCollector):
             # No point in finding packages when collecting doctests.
             if not self.config.getoption("doctestmodules", False):
                 pm = self.config.pluginmanager
+                confcutdir = py.path.local(pm._confcutdir) if pm._confcutdir else None
                 for parent in reversed(argpath.parts()):
-                    if pm._confcutdir and pm._confcutdir.relto(parent):
+                    if confcutdir and confcutdir.relto(parent):
                         break
 
                     if parent.isdir():
diff --git a/src/_pytest/nodes.py b/src/_pytest/nodes.py
index 27434fb6a..98bd581b9 100644
--- a/src/_pytest/nodes.py
+++ b/src/_pytest/nodes.py
@@ -520,7 +520,7 @@ class FSCollector(Collector):
         """The public constructor."""
         return super().from_parent(parent=parent, fspath=fspath, **kw)
 
-    def gethookproxy(self, fspath: py.path.local):
+    def gethookproxy(self, fspath: "os.PathLike[str]"):
         warnings.warn(FSCOLLECTOR_GETHOOKPROXY_ISINITPATH, stacklevel=2)
         return self.session.gethookproxy(fspath)
 
diff --git a/src/_pytest/python.py b/src/_pytest/python.py
index e48e7531c..407f924a5 100644
--- a/src/_pytest/python.py
+++ b/src/_pytest/python.py
@@ -653,7 +653,7 @@ class Package(Module):
             func = partial(_call_with_optional_argument, teardown_module, self.obj)
             self.addfinalizer(func)
 
-    def gethookproxy(self, fspath: py.path.local):
+    def gethookproxy(self, fspath: "os.PathLike[str]"):
         warnings.warn(FSCOLLECTOR_GETHOOKPROXY_ISINITPATH, stacklevel=2)
         return self.session.gethookproxy(fspath)
 
diff --git a/testing/python/fixtures.py b/testing/python/fixtures.py
index 94547dd24..ac62de608 100644
--- a/testing/python/fixtures.py
+++ b/testing/python/fixtures.py
@@ -8,6 +8,7 @@ from _pytest.compat import getfuncargnames
 from _pytest.config import ExitCode
 from _pytest.fixtures import FixtureRequest
 from _pytest.pytester import get_public_names
+from _pytest.pytester import Pytester
 from _pytest.pytester import Testdir
 
 
@@ -1961,8 +1962,10 @@ class TestAutouseManagement:
         reprec = testdir.inline_run("-v", "-s")
         reprec.assertoutcome(passed=4)
 
-    def test_class_function_parametrization_finalization(self, testdir):
-        p = testdir.makeconftest(
+    def test_class_function_parametrization_finalization(
+        self, pytester: Pytester
+    ) -> None:
+        p = pytester.makeconftest(
             """
             import pytest
             import pprint
@@ -1984,7 +1987,7 @@ class TestAutouseManagement:
                 request.addfinalizer(fin)
         """
         )
-        testdir.makepyfile(
+        pytester.makepyfile(
             """
             import pytest
 
@@ -1996,8 +1999,7 @@ class TestAutouseManagement:
                     pass
         """
         )
-        confcut = f"--confcutdir={testdir.tmpdir}"
-        reprec = testdir.inline_run("-v", "-s", confcut)
+        reprec = pytester.inline_run("-v", "-s", "--confcutdir", pytester.path)
         reprec.assertoutcome(passed=8)
         config = reprec.getcalls("pytest_unconfigure")[0].config
         values = config.pluginmanager._getconftestmodules(p, importmode="prepend")[
diff --git a/testing/test_collection.py b/testing/test_collection.py
index 1138c2bd6..862c1aba8 100644
--- a/testing/test_collection.py
+++ b/testing/test_collection.py
@@ -364,7 +364,9 @@ class TestCustomConftests:
     def test_collectignore_exclude_on_option(self, pytester: Pytester) -> None:
         pytester.makeconftest(
             """
-            collect_ignore = ['hello', 'test_world.py']
+            import py
+            from pathlib import Path
+            collect_ignore = [py.path.local('hello'), 'test_world.py', Path('bye')]
             def pytest_addoption(parser):
                 parser.addoption("--XX", action="store_true", default=False)
             def pytest_configure(config):
diff --git a/testing/test_config.py b/testing/test_config.py
index b931797d4..eacc9c9eb 100644
--- a/testing/test_config.py
+++ b/testing/test_config.py
@@ -574,16 +574,16 @@ class TestConfigAPI:
             config.getvalue("x")
         assert config.getoption("x", 1) == 1
 
-    def test_getconftest_pathlist(self, pytester: Pytester, tmpdir) -> None:
-        somepath = tmpdir.join("x", "y", "z")
-        p = tmpdir.join("conftest.py")
-        p.write("pathlist = ['.', %r]" % str(somepath))
+    def test_getconftest_pathlist(self, pytester: Pytester, tmp_path: Path) -> None:
+        somepath = tmp_path.joinpath("x", "y", "z")
+        p = tmp_path.joinpath("conftest.py")
+        p.write_text(f"pathlist = ['.', {str(somepath)!r}]")
         config = pytester.parseconfigure(p)
-        assert config._getconftest_pathlist("notexist", path=tmpdir) is None
-        pl = config._getconftest_pathlist("pathlist", path=tmpdir) or []
+        assert config._getconftest_pathlist("notexist", path=tmp_path) is None
+        pl = config._getconftest_pathlist("pathlist", path=tmp_path) or []
         print(pl)
         assert len(pl) == 2
-        assert pl[0] == tmpdir
+        assert pl[0] == tmp_path
         assert pl[1] == somepath
 
     @pytest.mark.parametrize("maybe_type", ["not passed", "None", '"string"'])
@@ -1935,10 +1935,10 @@ class TestPytestPluginsVariable:
         assert msg not in res.stdout.str()
 
 
-def test_conftest_import_error_repr(tmpdir: py.path.local) -> None:
+def test_conftest_import_error_repr(tmp_path: Path) -> None:
     """`ConftestImportFailure` should use a short error message and readable
     path to the failed conftest.py file."""
-    path = tmpdir.join("foo/conftest.py")
+    path = tmp_path.joinpath("foo/conftest.py")
     with pytest.raises(
         ConftestImportFailure,
         match=re.escape(f"RuntimeError: some error (from {path})"),
diff --git a/testing/test_conftest.py b/testing/test_conftest.py
index 638321728..36e83191b 100644
--- a/testing/test_conftest.py
+++ b/testing/test_conftest.py
@@ -4,6 +4,7 @@ import textwrap
 from pathlib import Path
 from typing import cast
 from typing import Dict
+from typing import Generator
 from typing import List
 from typing import Optional
 
@@ -15,7 +16,7 @@ from _pytest.config import PytestPluginManager
 from _pytest.monkeypatch import MonkeyPatch
 from _pytest.pathlib import symlink_or_skip
 from _pytest.pytester import Pytester
-from _pytest.pytester import Testdir
+from _pytest.tmpdir import TempPathFactory
 
 
 def ConftestWithSetinitial(path) -> PytestPluginManager:
@@ -25,12 +26,12 @@ def ConftestWithSetinitial(path) -> PytestPluginManager:
 
 
 def conftest_setinitial(
-    conftest: PytestPluginManager, args, confcutdir: Optional[py.path.local] = None
+    conftest: PytestPluginManager, args, confcutdir: Optional["os.PathLike[str]"] = None
 ) -> None:
     class Namespace:
         def __init__(self) -> None:
             self.file_or_dir = args
-            self.confcutdir = str(confcutdir)
+            self.confcutdir = os.fspath(confcutdir) if confcutdir is not None else None
             self.noconftest = False
             self.pyargs = False
             self.importmode = "prepend"
@@ -42,54 +43,58 @@ def conftest_setinitial(
 @pytest.mark.usefixtures("_sys_snapshot")
 class TestConftestValueAccessGlobal:
     @pytest.fixture(scope="module", params=["global", "inpackage"])
-    def basedir(self, request, tmpdir_factory):
-        tmpdir = tmpdir_factory.mktemp("basedir", numbered=True)
-        tmpdir.ensure("adir/conftest.py").write("a=1 ; Directory = 3")
-        tmpdir.ensure("adir/b/conftest.py").write("b=2 ; a = 1.5")
+    def basedir(
+        self, request, tmp_path_factory: TempPathFactory
+    ) -> Generator[Path, None, None]:
+        tmpdir = tmp_path_factory.mktemp("basedir", numbered=True)
+        tmpdir.joinpath("adir/b").mkdir(parents=True)
+        tmpdir.joinpath("adir/conftest.py").write_text("a=1 ; Directory = 3")
+        tmpdir.joinpath("adir/b/conftest.py").write_text("b=2 ; a = 1.5")
         if request.param == "inpackage":
-            tmpdir.ensure("adir/__init__.py")
-            tmpdir.ensure("adir/b/__init__.py")
+            tmpdir.joinpath("adir/__init__.py").touch()
+            tmpdir.joinpath("adir/b/__init__.py").touch()
 
         yield tmpdir
 
-    def test_basic_init(self, basedir):
+    def test_basic_init(self, basedir: Path) -> None:
         conftest = PytestPluginManager()
-        p = basedir.join("adir")
+        p = basedir / "adir"
         assert conftest._rget_with_confmod("a", p, importmode="prepend")[1] == 1
 
-    def test_immediate_initialiation_and_incremental_are_the_same(self, basedir):
+    def test_immediate_initialiation_and_incremental_are_the_same(
+        self, basedir: Path
+    ) -> None:
         conftest = PytestPluginManager()
         assert not len(conftest._dirpath2confmods)
         conftest._getconftestmodules(basedir, importmode="prepend")
         snap1 = len(conftest._dirpath2confmods)
         assert snap1 == 1
-        conftest._getconftestmodules(basedir.join("adir"), importmode="prepend")
+        conftest._getconftestmodules(basedir / "adir", importmode="prepend")
         assert len(conftest._dirpath2confmods) == snap1 + 1
-        conftest._getconftestmodules(basedir.join("b"), importmode="prepend")
+        conftest._getconftestmodules(basedir / "b", importmode="prepend")
         assert len(conftest._dirpath2confmods) == snap1 + 2
 
-    def test_value_access_not_existing(self, basedir):
+    def test_value_access_not_existing(self, basedir: Path) -> None:
         conftest = ConftestWithSetinitial(basedir)
         with pytest.raises(KeyError):
             conftest._rget_with_confmod("a", basedir, importmode="prepend")
 
-    def test_value_access_by_path(self, basedir):
+    def test_value_access_by_path(self, basedir: Path) -> None:
         conftest = ConftestWithSetinitial(basedir)
-        adir = basedir.join("adir")
+        adir = basedir / "adir"
         assert conftest._rget_with_confmod("a", adir, importmode="prepend")[1] == 1
         assert (
-            conftest._rget_with_confmod("a", adir.join("b"), importmode="prepend")[1]
-            == 1.5
+            conftest._rget_with_confmod("a", adir / "b", importmode="prepend")[1] == 1.5
         )
 
-    def test_value_access_with_confmod(self, basedir):
-        startdir = basedir.join("adir", "b")
-        startdir.ensure("xx", dir=True)
+    def test_value_access_with_confmod(self, basedir: Path) -> None:
+        startdir = basedir / "adir" / "b"
+        startdir.joinpath("xx").mkdir()
         conftest = ConftestWithSetinitial(startdir)
         mod, value = conftest._rget_with_confmod("a", startdir, importmode="prepend")
         assert value == 1.5
         path = py.path.local(mod.__file__)
-        assert path.dirpath() == basedir.join("adir", "b")
+        assert path.dirpath() == basedir / "adir" / "b"
         assert path.purebasename.startswith("conftest")
 
 
@@ -102,12 +107,12 @@ def test_conftest_in_nonpkg_with_init(tmp_path: Path, _sys_snapshot) -> None:
     ConftestWithSetinitial(tmp_path.joinpath("adir-1.0", "b"))
 
 
-def test_doubledash_considered(testdir: Testdir) -> None:
-    conf = testdir.mkdir("--option")
-    conf.join("conftest.py").ensure()
+def test_doubledash_considered(pytester: Pytester) -> None:
+    conf = pytester.mkdir("--option")
+    conf.joinpath("conftest.py").touch()
     conftest = PytestPluginManager()
-    conftest_setinitial(conftest, [conf.basename, conf.basename])
-    values = conftest._getconftestmodules(py.path.local(conf), importmode="prepend")
+    conftest_setinitial(conftest, [conf.name, conf.name])
+    values = conftest._getconftestmodules(conf, importmode="prepend")
     assert len(values) == 1
 
 
@@ -127,15 +132,18 @@ def test_conftest_global_import(pytester: Pytester) -> None:
     pytester.makeconftest("x=3")
     p = pytester.makepyfile(
         """
-        import py, pytest
+        from pathlib import Path
+        import pytest
         from _pytest.config import PytestPluginManager
         conf = PytestPluginManager()
-        mod = conf._importconftest(py.path.local("conftest.py"), importmode="prepend")
+        mod = conf._importconftest(Path("conftest.py"), importmode="prepend")
         assert mod.x == 3
         import conftest
         assert conftest is mod, (conftest, mod)
-        subconf = py.path.local().ensure("sub", "conftest.py")
-        subconf.write("y=4")
+        sub = Path("sub")
+        sub.mkdir()
+        subconf = sub / "conftest.py"
+        subconf.write_text("y=4")
         mod2 = conf._importconftest(subconf, importmode="prepend")
         assert mod != mod2
         assert mod2.y == 4
@@ -147,19 +155,19 @@ def test_conftest_global_import(pytester: Pytester) -> None:
     assert res.ret == 0
 
 
-def test_conftestcutdir(testdir: Testdir) -> None:
-    conf = testdir.makeconftest("")
-    p = testdir.mkdir("x")
+def test_conftestcutdir(pytester: Pytester) -> None:
+    conf = pytester.makeconftest("")
+    p = pytester.mkdir("x")
     conftest = PytestPluginManager()
-    conftest_setinitial(conftest, [testdir.tmpdir], confcutdir=p)
+    conftest_setinitial(conftest, [pytester.path], confcutdir=p)
     values = conftest._getconftestmodules(p, importmode="prepend")
     assert len(values) == 0
-    values = conftest._getconftestmodules(conf.dirpath(), importmode="prepend")
+    values = conftest._getconftestmodules(conf.parent, importmode="prepend")
     assert len(values) == 0
     assert Path(conf) not in conftest._conftestpath2mod
     # but we can still import a conftest directly
     conftest._importconftest(conf, importmode="prepend")
-    values = conftest._getconftestmodules(conf.dirpath(), importmode="prepend")
+    values = conftest._getconftestmodules(conf.parent, importmode="prepend")
     assert values[0].__file__.startswith(str(conf))
     # and all sub paths get updated properly
     values = conftest._getconftestmodules(p, importmode="prepend")
@@ -170,10 +178,8 @@ def test_conftestcutdir(testdir: Testdir) -> None:
 def test_conftestcutdir_inplace_considered(pytester: Pytester) -> None:
     conf = pytester.makeconftest("")
     conftest = PytestPluginManager()
-    conftest_setinitial(conftest, [conf.parent], confcutdir=py.path.local(conf.parent))
-    values = conftest._getconftestmodules(
-        py.path.local(conf.parent), importmode="prepend"
-    )
+    conftest_setinitial(conftest, [conf.parent], confcutdir=conf.parent)
+    values = conftest._getconftestmodules(conf.parent, importmode="prepend")
     assert len(values) == 1
     assert values[0].__file__.startswith(str(conf))
 
@@ -184,7 +190,7 @@ def test_setinitial_conftest_subdirs(pytester: Pytester, name: str) -> None:
     subconftest = sub.joinpath("conftest.py")
     subconftest.touch()
     conftest = PytestPluginManager()
-    conftest_setinitial(conftest, [sub.parent], confcutdir=py.path.local(pytester.path))
+    conftest_setinitial(conftest, [sub.parent], confcutdir=pytester.path)
     key = subconftest.resolve()
     if name not in ("whatever", ".dotdir"):
         assert key in conftest._conftestpath2mod
@@ -337,22 +343,19 @@ def test_conftest_existing_junitxml(pytester: Pytester) -> None:
     result.stdout.fnmatch_lines(["*--xyz*"])
 
 
-def test_conftest_import_order(testdir: Testdir, monkeypatch: MonkeyPatch) -> None:
-    ct1 = testdir.makeconftest("")
-    sub = testdir.mkdir("sub")
-    ct2 = sub.join("conftest.py")
-    ct2.write("")
+def test_conftest_import_order(pytester: Pytester, monkeypatch: MonkeyPatch) -> None:
+    ct1 = pytester.makeconftest("")
+    sub = pytester.mkdir("sub")
+    ct2 = sub / "conftest.py"
+    ct2.write_text("")
 
     def impct(p, importmode):
         return p
 
     conftest = PytestPluginManager()
-    conftest._confcutdir = testdir.tmpdir
+    conftest._confcutdir = pytester.path
     monkeypatch.setattr(conftest, "_importconftest", impct)
-    mods = cast(
-        List[py.path.local],
-        conftest._getconftestmodules(py.path.local(sub), importmode="prepend"),
-    )
+    mods = cast(List[Path], conftest._getconftestmodules(sub, importmode="prepend"))
     expected = [ct1, ct2]
     assert mods == expected
 
diff --git a/testing/test_pluginmanager.py b/testing/test_pluginmanager.py
index 2099f5ae1..89f10a7db 100644
--- a/testing/test_pluginmanager.py
+++ b/testing/test_pluginmanager.py
@@ -8,6 +8,7 @@ from _pytest.config import ExitCode
 from _pytest.config import PytestPluginManager
 from _pytest.config.exceptions import UsageError
 from _pytest.main import Session
+from _pytest.pytester import Pytester
 
 
 @pytest.fixture
@@ -16,14 +17,16 @@ def pytestpm() -> PytestPluginManager:
 
 
 class TestPytestPluginInteractions:
-    def test_addhooks_conftestplugin(self, testdir, _config_for_test):
-        testdir.makepyfile(
+    def test_addhooks_conftestplugin(
+        self, pytester: Pytester, _config_for_test
+    ) -> None:
+        pytester.makepyfile(
             newhooks="""
             def pytest_myhook(xyz):
                 "new hook"
         """
         )
-        conf = testdir.makeconftest(
+        conf = pytester.makeconftest(
             """
             import newhooks
             def pytest_addhooks(pluginmanager):
@@ -54,10 +57,10 @@ class TestPytestPluginInteractions:
         assert res.ret != 0
         res.stderr.fnmatch_lines(["*did not find*sys*"])
 
-    def test_do_option_postinitialize(self, testdir):
-        config = testdir.parseconfigure()
+    def test_do_option_postinitialize(self, pytester: Pytester) -> None:
+        config = pytester.parseconfigure()
         assert not hasattr(config.option, "test123")
-        p = testdir.makepyfile(
+        p = pytester.makepyfile(
             """
             def pytest_addoption(parser):
                 parser.addoption('--test123', action="store_true",
@@ -120,20 +123,20 @@ class TestPytestPluginInteractions:
         finally:
             undo()
 
-    def test_hook_proxy(self, testdir):
+    def test_hook_proxy(self, pytester: Pytester) -> None:
         """Test the gethookproxy function(#2016)"""
-        config = testdir.parseconfig()
+        config = pytester.parseconfig()
         session = Session.from_config(config)
-        testdir.makepyfile(**{"tests/conftest.py": "", "tests/subdir/conftest.py": ""})
+        pytester.makepyfile(**{"tests/conftest.py": "", "tests/subdir/conftest.py": ""})
 
-        conftest1 = testdir.tmpdir.join("tests/conftest.py")
-        conftest2 = testdir.tmpdir.join("tests/subdir/conftest.py")
+        conftest1 = pytester.path.joinpath("tests/conftest.py")
+        conftest2 = pytester.path.joinpath("tests/subdir/conftest.py")
 
         config.pluginmanager._importconftest(conftest1, importmode="prepend")
-        ihook_a = session.gethookproxy(testdir.tmpdir.join("tests"))
+        ihook_a = session.gethookproxy(pytester.path / "tests")
         assert ihook_a is not None
         config.pluginmanager._importconftest(conftest2, importmode="prepend")
-        ihook_b = session.gethookproxy(testdir.tmpdir.join("tests"))
+        ihook_b = session.gethookproxy(pytester.path / "tests")
         assert ihook_a is not ihook_b
 
     def test_hook_with_addoption(self, testdir):