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diff --git a/pydis_site/apps/timeline/README.md b/pydis_site/apps/timeline/README.md
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+# The "timeline" app
+
+The [timeline page](https://www.pythondiscord.com/timeline/) on our website is
+powered by this Django application.
+
+## The entries
+
+Timeline entries are written in markdown files with YAML frontmatter under the
+`entries` directory.
+
+Each file represents a timeline entry. The files are named with the format
+`<date>_<name>.md`:
+- `date`: The date is in the `YYYY-MM-DD` format, intended for easy sorting in
+  editor/shell command directory listings. It's also used to sort the entries
+  before rendering the timeline page.
+- `name`: The name component is an arbitrary slug in **kebab-case**. This is used
+  for linking to individual timeline entries on the page, and will be set in
+  the `id` attribute.
+
+Each file contains:
+- YAML frontmatter. This defines some metadata shown next to each entry in
+  the timeline, including:
+  - Date: User-facing date label.
+  - Icon: The CSS class to be used for the icon. Set to `pydis` to use the
+    pydis logo image.
+  - Icon color: The CSS class that sets the background color of the icon. Leave
+    empty if the pydis logo is used.
+- Markdown content.
+
+
+## Directory structure
+
+The app has a single view in `views.py` that takes care of reading the `.md`
+files in the `entires` directory. This is a standard Django view, mounted in
+`urls.py` as usual.
+
+The `tests` directory validates that our redirects and helper functions work as
+expected. If you made changes to the app and are looking for guidance on adding
+new tests, the [Django tutorial introducing automated
+testing](https://docs.djangoproject.com/en/dev/intro/tutorial05/) is a good
+place to start.
+
+This application does not use the database and as such does not have models nor
+migrations.
diff --git a/pydis_site/apps/timeline/__init__.py b/pydis_site/apps/timeline/__init__.py
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diff --git a/pydis_site/apps/timeline/apps.py b/pydis_site/apps/timeline/apps.py
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+++ b/pydis_site/apps/timeline/apps.py
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+from pathlib import Path
+
+from django.apps import AppConfig
+import frontmatter
+import markdown
+
+from pydis_site import settings
+
+
+ENTRIES_PATH = Path(settings.BASE_DIR, "pydis_site", "apps", "timeline", "entries")
+
+
+class TimelineConfig(AppConfig):
+    """AppConfig instance for Timeline app."""
+
+    name = 'pydis_site.apps.timeline'
+
+    def ready(self) -> None:
+        """Fetch all the timeline entries."""
+        self.entries = []
+
+        for path in ENTRIES_PATH.rglob("*.md"):
+            metadata, content = frontmatter.parse(path.read_text(encoding="utf-8"))
+
+            md = markdown.Markdown()
+            html = str(md.convert(content))
+
+            # Strip `.md` file extension from filename and split it into the
+            # date (for sorting) and slug (for linking).
+            key, slug = path.name[:-3].split("_")
+            entry = {
+                "key": key,
+                "slug": slug,
+                "title": metadata["title"],
+                "date": metadata["date"],
+                "icon": metadata["icon"],
+                # This key might not be used if the icon uses the pydis logo.
+                "icon_color": metadata.get("icon_color"),
+                "content": html,
+            }
+
+            self.entries.append(entry)
+
+        # Sort the entries in reverse-chronological order.
+        self.entries.sort(key=lambda e: e['key'], reverse=True)
diff --git a/pydis_site/apps/timeline/entries/2023-01-30_retirement-of-joe-and-sebastiaan.md b/pydis_site/apps/timeline/entries/2023-01-30_retirement-of-joe-and-sebastiaan.md
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+++ b/pydis_site/apps/timeline/entries/2023-01-30_retirement-of-joe-and-sebastiaan.md
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+---
+title: Retirement of Joe and Sebastiaan
+date: 2023-01-30
+icon: pydis
+---
+
+Having been at the helm of Python Discord for over 5 and 3 years respectively,
+Joe and Sebastiaan retire and step down. They gain the **@Founders** role and
+continue as advisors to the **@Directors**, the new name of the original
+**@Owners** role.
+
+At the same time, Mina and Zig join Leon as co-directors.
diff --git a/pydis_site/apps/timeline/entries/2023-07-11_new-paste-service.md b/pydis_site/apps/timeline/entries/2023-07-11_new-paste-service.md
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+++ b/pydis_site/apps/timeline/entries/2023-07-11_new-paste-service.md
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+---
+title: Switch to new paste service
+date: 2023-07-11
+icon: fa-regular fa-clipboard
+icon_color: pastel-pink
+---
+
+We migrate over to [pinnwand](https://github.com/supakeen/pinnwand) as the
+service that powers our paste bin over at <https://paste.pythondiscord.com/>.
+We made the switch as it comes with native light/dark modes, support for
+multi-file pastes, additional support for text highlighting languages, and
+plus, it's written in Python!
diff --git a/pydis_site/apps/timeline/urls.py b/pydis_site/apps/timeline/urls.py
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+++ b/pydis_site/apps/timeline/urls.py
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+from django_distill import distill_path
+
+from .views import TimelineView
+
+app_name = "timeline"
+
+urlpatterns = [
+    distill_path("", TimelineView.as_view(), name="index"),
+]
diff --git a/pydis_site/apps/timeline/views.py b/pydis_site/apps/timeline/views.py
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+++ b/pydis_site/apps/timeline/views.py
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+from django.apps import apps
+from django.core.handlers.wsgi import WSGIRequest
+from django.http import HttpResponse
+from django.shortcuts import render
+from django.views import View
+
+APP_NAME = "timeline"
+
+class TimelineView(View):
+    """A vertical timeline showcasing milestones in the history of Python Discord."""
+
+    def get(self, request: WSGIRequest) -> HttpResponse:
+        """Render the timeline."""
+        app = apps.get_app_config(APP_NAME)
+
+        return render(
+            request,
+            template_name="timeline/timeline.html",
+            context={ "entries": app.entries },
+        )