diff --git a/docs/pyproject.md b/docs/pyproject.md
index 96c40280e40..73900c092db 100644
--- a/docs/pyproject.md
+++ b/docs/pyproject.md
@@ -73,6 +73,29 @@ The readme file of the package. **Optional**
 
 The file can be either `README.rst` or `README.md`.
 
+```toml
+[tool.poetry]
+# ...
+readme = "README.rst"
+```
+
+If you want to use multiple readme files, you can by wrapping the files in a list.
+
+```toml
+[tool.poetry]
+# ...
+readme = [
+    "README.rst",
+    "CHANGELOG.rst"
+]
+```
+
+{{% note %}}
+Note that a line break (`\n`) will be added between each file in the generated readme.
+
+Additionally, all the listed files must be of same type, i.e. you cannot mix `.rst` and `.md`.
+{{% /note %}}
+
 ## homepage
 
 An URL to the website of the project. **Optional**
diff --git a/src/poetry/json/schemas/poetry-schema.json b/src/poetry/json/schemas/poetry-schema.json
index fe916f1e04e..b5b5bab77a8 100644
--- a/src/poetry/json/schemas/poetry-schema.json
+++ b/src/poetry/json/schemas/poetry-schema.json
@@ -54,8 +54,19 @@
       "$ref": "#/definitions/maintainers"
     },
     "readme": {
-      "type": "string",
-      "description": "The path to the README file"
+      "anyOf": [
+        {
+          "type": "string",
+          "description": "The path to the README file."
+        },
+        {
+          "type": "array",
+          "description": "A list of paths to the readme files.",
+          "items": {
+            "type": "string"
+          }
+        }
+      ]
     },
     "classifiers": {
       "type": "array",