diff --git a/convention-template/config/settings.py.jinja b/convention-template/config/settings.py.jinja
index 38ef3b9a..0e4e6131 100644
--- a/convention-template/config/settings.py.jinja
+++ b/convention-template/config/settings.py.jinja
@@ -109,6 +109,8 @@ INSTALLED_APPS = [
     "waffle",
     # Convention admin utilities and seeding commands
     "nomnom.convention_admin",
+    # Admin-configurable homepage timeline
+    "nomnom.timeline",
 ]
 
 SITE_ID = 1
diff --git a/nomnom_dev/settings.py b/nomnom_dev/settings.py
index 9f93cc5a..39530d84 100644
--- a/nomnom_dev/settings.py
+++ b/nomnom_dev/settings.py
@@ -135,6 +135,8 @@ def __bool__(self):  # if using Python 2, use __nonzero__ instead
     "nomnom.hugopacket",
     # Convention admin utilities and seeding commands
     "nomnom.convention_admin",
+    # Admin-configurable homepage timeline
+    "nomnom.timeline",
 ]
 
 SITE_ID = 1
diff --git a/src/nomnom/base/templates/nomnom/index.html b/src/nomnom/base/templates/nomnom/index.html
index 64486983..cee540bb 100644
--- a/src/nomnom/base/templates/nomnom/index.html
+++ b/src/nomnom/base/templates/nomnom/index.html
@@ -6,6 +6,9 @@
             {% if not user.is_authenticated %}
                 {% include "bits/login_forms.html" %}
             {% else %}
+                {% switch "timeline" %}
+                    {% include "timeline/timeline.html" %}
+                {% endswitch %}
                 <!-- For mobile: separate sections stacked -->
                 <div class="d-block d-md-none">
                     <!-- WSFS Elections Section for Mobile -->
diff --git a/src/nomnom/base/views.py b/src/nomnom/base/views.py
index 1504c1f0..705fe349 100644
--- a/src/nomnom/base/views.py
+++ b/src/nomnom/base/views.py
@@ -5,12 +5,10 @@
 
 
 def index(request: HttpRequest) -> HttpResponse:
+    context = {}
     if request.user.is_authenticated:
-        context = {}
         for receiver, response in index_content_load.send(sender=None, request=request):
             if isinstance(response, dict):
                 context.update(response)
 
-    else:
-        context = {}
     return render(request, "nomnom/index.html", context)
diff --git a/src/nomnom/nominate/static/css/layout.css b/src/nomnom/nominate/static/css/layout.css
index c399a156..85115c19 100644
--- a/src/nomnom/nominate/static/css/layout.css
+++ b/src/nomnom/nominate/static/css/layout.css
@@ -70,3 +70,208 @@
   position: relative;
   z-index: 1;
 }
+
+.timeline {
+  margin: 0 1rem 2rem 0;
+}
+
+.timeline-toggle,
+.timeline-toggle-label {
+  display: none;
+}
+
+.timeline-events {
+  list-style: none;
+  margin: 0;
+  padding: 0 0 0 2rem;
+  display: flex;
+  flex-wrap: wrap;
+  align-items: flex-start;
+  row-gap: 1.25rem;
+}
+
+.timeline-event {
+  flex: 1 1 3rem;
+  position: relative;
+  display: flex;
+  flex-direction: column;
+  align-items: center;
+  text-align: center;
+  padding: 0 0.5rem;
+  max-width: 8rem;
+}
+
+.timeline-event:first-child {
+  margin-left: -2rem;
+}
+
+.timeline-event::before,
+.timeline-event::after {
+  content: "";
+  position: absolute;
+  top: calc(0.75rem - 2.5px);
+  height: 5px;
+  background: var(--timeline-color, #555);
+  z-index: 0;
+}
+
+.timeline-event::before {
+  left: 0;
+  right: 50%;
+}
+
+.timeline-event::after {
+  left: 50%;
+  right: 0;
+}
+
+.timeline-event:first-child::before,
+.timeline-event:last-child::after {
+  content: none;
+}
+
+.timeline-bubble {
+  width: 1.5rem;
+  height: 1.5rem;
+  border-radius: 50%;
+  border: 5px solid var(--timeline-color, #555);
+  background: #fff;
+  position: relative;
+  z-index: 1;
+  margin-bottom: 0.4rem;
+}
+
+.timeline-event.is-complete .timeline-bubble {
+  background: var(--timeline-color, #555);
+}
+
+.timeline-label {
+  font-weight: bold;
+  font-size: 0.8rem;
+  line-height: 1.15;
+}
+
+.timeline-date {
+  font-size: 0.75rem;
+  margin-top: 0.15rem;
+}
+
+.timeline-footnote {
+  font-size: 0.7rem;
+  margin-top: 0.5rem;
+  margin-bottom: 0;
+}
+
+@media (max-width: 767.98px) {
+  .timeline-events {
+    flex-direction: column;
+    align-items: flex-start;
+    flex-wrap: nowrap;
+    padding-left: 0;
+    row-gap: 0;
+  }
+
+  .timeline-event {
+    display: grid;
+    grid-template-columns: auto 1fr;
+    grid-template-rows: auto auto;
+    column-gap: 0.75rem;
+    flex: 0 0 auto;
+    max-width: none;
+    padding: 0.5rem 0;
+    width: 100%;
+    text-align: left;
+  }
+
+  .timeline-event:first-child {
+    margin-left: 0;
+  }
+
+  .timeline-bubble {
+    grid-column: 1;
+    grid-row: 1 / span 2;
+    align-self: center;
+    margin-bottom: 0;
+  }
+
+  .timeline-label {
+    grid-column: 2;
+    grid-row: 1;
+    align-self: end;
+  }
+
+  .timeline-date {
+    grid-column: 2;
+    grid-row: 2;
+    align-self: start;
+  }
+
+  .timeline-event::before,
+  .timeline-event::after {
+    left: calc(0.75rem - 2.5px);
+    right: auto;
+    top: auto;
+    width: 5px;
+    height: 50%;
+  }
+
+  .timeline-event::before {
+    top: 0;
+  }
+
+  .timeline-event::after {
+    bottom: 0;
+  }
+
+  .timeline-label,
+  .timeline-date {
+    display: block;
+    text-align: left;
+  }
+
+  .timeline {
+    position: relative;
+  }
+
+  .timeline-toggle {
+    display: block;
+    position: absolute;
+    width: 1px;
+    height: 1px;
+    padding: 0;
+    margin: -1px;
+    overflow: hidden;
+    clip: rect(0, 0, 0, 0);
+    white-space: nowrap;
+    border: 0;
+  }
+
+  .timeline-toggle-label {
+    display: block;
+    position: absolute;
+    inset: 0;
+    cursor: pointer;
+    z-index: 2;
+  }
+
+  .timeline-toggle:focus-visible ~ .timeline-toggle-label {
+    outline: auto;
+    outline-offset: 2px;
+  }
+
+  .timeline-toggle:not(:checked) ~ .timeline-events .timeline-event:not(.timeline-event--shown) {
+    display: none;
+  }
+
+  .timeline-toggle:not(:checked) ~ .timeline-events .timeline-event:not(.timeline-event--shown) + .timeline-event--shown::before {
+    background:
+      linear-gradient(var(--timeline-color, #555), var(--timeline-color, #555)) center top 2px / 5px 5px no-repeat,
+      linear-gradient(var(--timeline-color, #555), var(--timeline-color, #555)) center top 10px / 5px 5px no-repeat;
+  }
+
+  .timeline-toggle:not(:checked) ~ .timeline-events .timeline-event--shown:has(+ .timeline-event:not(.timeline-event--shown))::after {
+    background:
+      linear-gradient(var(--timeline-color, #555), var(--timeline-color, #555)) center bottom 2px / 5px 5px no-repeat,
+      linear-gradient(var(--timeline-color, #555), var(--timeline-color, #555)) center bottom 10px / 5px 5px no-repeat;
+  }
+}
diff --git a/src/nomnom/test_settings.py b/src/nomnom/test_settings.py
index 2916452a..ec0b3ec8 100644
--- a/src/nomnom/test_settings.py
+++ b/src/nomnom/test_settings.py
@@ -39,6 +39,7 @@
     "nomnom.canonicalize",
     "nomnom.wsfs",
     "nomnom.convention_admin",
+    "nomnom.timeline",
 ]
 NPLUSONE_RAISE = True
 
diff --git a/src/nomnom/timeline/__init__.py b/src/nomnom/timeline/__init__.py
new file mode 100644
index 00000000..e69de29b
diff --git a/src/nomnom/timeline/admin.py b/src/nomnom/timeline/admin.py
new file mode 100644
index 00000000..1c5626ce
--- /dev/null
+++ b/src/nomnom/timeline/admin.py
@@ -0,0 +1,10 @@
+from django.contrib import admin
+
+from . import models
+
+
+@admin.register(models.TimelineEvent)
+class TimelineEventAdmin(admin.ModelAdmin):
+    list_display = ["label", "date", "provisional", "position", "complete"]
+    list_editable = ["position", "complete"]
+    ordering = ["position"]
diff --git a/src/nomnom/timeline/apps.py b/src/nomnom/timeline/apps.py
new file mode 100644
index 00000000..9730f704
--- /dev/null
+++ b/src/nomnom/timeline/apps.py
@@ -0,0 +1,16 @@
+from django.apps import AppConfig
+
+
+class TimelineConfig(AppConfig):
+    default_auto_field = "django.db.models.BigAutoField"
+    name = "nomnom.timeline"
+
+    def ready(self) -> None:
+        self.enable_signals()
+
+        return super().ready()
+
+    def enable_signals(self):
+        from . import (
+            receivers,  # noqa: F401
+        )
diff --git a/src/nomnom/timeline/feature_switches.py b/src/nomnom/timeline/feature_switches.py
new file mode 100644
index 00000000..cab96f85
--- /dev/null
+++ b/src/nomnom/timeline/feature_switches.py
@@ -0,0 +1,3 @@
+"""Waffle switch name constants for the timeline feature."""
+
+SWITCH_TIMELINE = "timeline"
diff --git a/src/nomnom/timeline/migrations/0001_initial.py b/src/nomnom/timeline/migrations/0001_initial.py
new file mode 100644
index 00000000..ab8c5329
--- /dev/null
+++ b/src/nomnom/timeline/migrations/0001_initial.py
@@ -0,0 +1,51 @@
+# Generated by Django 5.2.11 on 2026-04-24 19:00
+
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+    initial = True
+
+    dependencies = []
+
+    operations = [
+        migrations.CreateModel(
+            name="TimelineEvent",
+            fields=[
+                (
+                    "id",
+                    models.BigAutoField(
+                        auto_created=True,
+                        primary_key=True,
+                        serialize=False,
+                        verbose_name="ID",
+                    ),
+                ),
+                ("label", models.CharField(max_length=255)),
+                (
+                    "date",
+                    models.CharField(
+                        help_text="e.g. 'Feb 12th 2026' or 'Early May 2026'.",
+                        max_length=255,
+                    ),
+                ),
+                ("position", models.PositiveSmallIntegerField(default=0)),
+                (
+                    "provisional",
+                    models.BooleanField(
+                        default=False,
+                        help_text="Whether to show a caveat about the date being provisional.",
+                    ),
+                ),
+                (
+                    "complete",
+                    models.BooleanField(
+                        default=False, help_text="Whether the event has passed."
+                    ),
+                ),
+            ],
+            options={
+                "ordering": ["position"],
+            },
+        ),
+    ]
diff --git a/src/nomnom/timeline/migrations/0002_create_timeline_switch.py b/src/nomnom/timeline/migrations/0002_create_timeline_switch.py
new file mode 100644
index 00000000..ec506729
--- /dev/null
+++ b/src/nomnom/timeline/migrations/0002_create_timeline_switch.py
@@ -0,0 +1,38 @@
+"""Data migration to create a feature flag toggle for the homepage timeline."""
+
+from django.db import migrations
+
+from nomnom.timeline.feature_switches import SWITCH_TIMELINE
+
+SWITCHES = [
+    {
+        "name": SWITCH_TIMELINE,
+        "active": False,
+        "note": "Toggle homepage timeline visibility",
+    },
+]
+
+
+def create_switches(apps, schema_editor):
+    Switch = apps.get_model("waffle", "Switch")
+    for switch in SWITCHES:
+        Switch.objects.get_or_create(
+            name=switch["name"],
+            defaults={"active": switch["active"], "note": switch["note"]},
+        )
+
+
+def delete_switches(apps, schema_editor):
+    Switch = apps.get_model("waffle", "Switch")
+    Switch.objects.filter(name__in=[s["name"] for s in SWITCHES]).delete()
+
+
+class Migration(migrations.Migration):
+    dependencies = [
+        ("waffle", "0004_update_everyone_nullbooleanfield"),
+        ("timeline", "0001_initial"),
+    ]
+
+    operations = [
+        migrations.RunPython(create_switches, delete_switches),
+    ]
diff --git a/src/nomnom/timeline/migrations/__init__.py b/src/nomnom/timeline/migrations/__init__.py
new file mode 100644
index 00000000..e69de29b
diff --git a/src/nomnom/timeline/models.py b/src/nomnom/timeline/models.py
new file mode 100644
index 00000000..2061a2df
--- /dev/null
+++ b/src/nomnom/timeline/models.py
@@ -0,0 +1,24 @@
+from django.db import models
+
+
+class TimelineEvent(models.Model):
+    class Meta:
+        ordering = ["position"]
+
+    label = models.CharField(max_length=255)
+    date = models.CharField(
+        max_length=255,
+        help_text="e.g. 'Feb 12th 2026' or 'Early May 2026'.",
+    )
+    position = models.PositiveSmallIntegerField(default=0)
+    provisional = models.BooleanField(
+        default=False,
+        help_text="Whether to show a caveat about the date being provisional.",
+    )
+    complete = models.BooleanField(
+        default=False,
+        help_text="Whether the event has passed.",
+    )
+
+    def __str__(self) -> str:
+        return self.label
diff --git a/src/nomnom/timeline/receivers.py b/src/nomnom/timeline/receivers.py
new file mode 100644
index 00000000..fa9e9a3e
--- /dev/null
+++ b/src/nomnom/timeline/receivers.py
@@ -0,0 +1,29 @@
+from waffle import switch_is_active
+
+from nomnom.base.signals import index_content_load
+from nomnom.timeline.feature_switches import SWITCH_TIMELINE
+
+from . import models
+
+
+def add_timeline_content(sender, request, **kwargs):
+    if not switch_is_active(SWITCH_TIMELINE):
+        return {}
+    timeline_events = list(models.TimelineEvent.objects.all())
+    _annotate_collapsed_visibility(timeline_events)
+    return {
+        "timeline_events": timeline_events,
+        "any_provisional": any(e.provisional for e in timeline_events),
+    }
+
+
+def _annotate_collapsed_visibility(events):
+    boundary = next(
+        (i - 1 for i, e in enumerate(events) if not e.complete),
+        len(events) - 1,
+    )
+    for i, event in enumerate(events):
+        event.shown_collapsed = i in (boundary, boundary + 1, boundary + 2)
+
+
+index_content_load.connect(add_timeline_content)
diff --git a/src/nomnom/timeline/templates/timeline/timeline.html b/src/nomnom/timeline/templates/timeline/timeline.html
new file mode 100644
index 00000000..0c1e1b18
--- /dev/null
+++ b/src/nomnom/timeline/templates/timeline/timeline.html
@@ -0,0 +1,35 @@
+{% load i18n %}
+{% if timeline_events %}
+    <section class="timeline" aria-label="{% translate 'Timeline' %}">
+        <input type="checkbox"
+               id="timeline-toggle"
+               class="timeline-toggle"
+               role="switch"
+               aria-controls="timeline-events"
+               aria-label="{% translate 'Toggle full timeline' %}">
+        <label for="timeline-toggle" class="timeline-toggle-label" aria-hidden="true"></label>
+        <ol id="timeline-events" class="timeline-events">
+            {% for event in timeline_events %}
+                <li class="timeline-event{% if event.shown_collapsed %} timeline-event--shown{% endif %}{% if event.complete %} is-complete{% endif %}">
+                    <span class="timeline-bubble" aria-hidden="true"></span>
+                    <span class="timeline-label">{{ event.label }}</span>
+                    <span class="visually-hidden">
+                        {% if event.complete %}
+                            ({% translate "completed" %})
+                        {% endif %}
+                    </span>
+                    <span class="timeline-date">
+                        {{ event.date }}
+                        {% if event.provisional %}
+                            <span aria-hidden="true">*</span>
+                            <span class="visually-hidden">({% translate "provisional" %})</span>
+                        {% endif %}
+                    </span>
+                </li>
+            {% endfor %}
+        </ol>
+        {% if any_provisional %}
+            <p class="timeline-footnote" aria-hidden="true">* {% translate "Dates are provisional and may change" %}</p>
+        {% endif %}
+    </section>
+{% endif %}