diff --git a/news/2877.bugfix b/news/2877.bugfix
new file mode 100644
index 0000000000..c5b23a31a3
--- /dev/null
+++ b/news/2877.bugfix
@@ -0,0 +1 @@
+Fixed a bug where `pipenv` crashes when the `WORKON_HOME` directory does not exist.
diff --git a/pipenv/utils.py b/pipenv/utils.py
index b7295c2921..0e1f851d1d 100644
--- a/pipenv/utils.py
+++ b/pipenv/utils.py
@@ -1281,7 +1281,10 @@ def get_workon_home():
             workon_home = os.path.join(
                 os.environ.get("XDG_DATA_HOME", "~/.local/share"), "virtualenvs"
             )
-    return Path(os.path.expandvars(workon_home)).expanduser()
+    # Create directory if it does not already exist
+    expanded_path = Path(os.path.expandvars(workon_home)).expanduser()
+    mkdir_p(str(expanded_path))
+    return expanded_path
 
 
 def is_virtual_environment(path):