diff --git a/backend/app/routers/library.py b/backend/app/routers/library.py
index 887b4fe..9ccf783 100644
--- a/backend/app/routers/library.py
+++ b/backend/app/routers/library.py
@@ -47,6 +47,50 @@ async def trigger_scan():
     
     return {"status": "success", "message": "Library scan started"}
 
+@router.get("/date_buckets")
+async def get_date_buckets(db: AsyncSession = Depends(get_db)):
+    """Aggregate non-discarded photos by year and month based on taken_at.
+    Used by the LeftSidebar 'By Date' subtree to render a year-then-month
+    drilldown without fetching every photo. Returns:
+        [{ year: 2026, count: 5, months: [{ month: 4, count: 5 }] }]
+    """
+    year_expr = func.strftime('%Y', Photo.taken_at)
+    month_expr = func.strftime('%m', Photo.taken_at)
+
+    result = await db.execute(
+        select(
+            year_expr.label('year'),
+            month_expr.label('month'),
+            func.count(Photo.id).label('count'),
+        )
+        .where(
+            Photo.is_discarded == False,  # noqa: E712
+            Photo.taken_at.is_not(None),
+        )
+        .group_by(year_expr, month_expr)
+        .order_by(year_expr.desc(), month_expr.desc())
+    )
+    rows = result.all()
+
+    years: dict[int, dict] = {}
+    for year_str, month_str, count in rows:
+        if not year_str or not month_str:
+            continue
+        try:
+            year = int(year_str)
+            month = int(month_str)
+        except ValueError:
+            continue
+        bucket = years.setdefault(
+            year, {'year': year, 'count': 0, 'months': []}
+        )
+        bucket['count'] += int(count)
+        bucket['months'].append({'month': month, 'count': int(count)})
+
+    # Already ordered by the SQL ORDER BY (newest first), preserve insertion.
+    return list(years.values())
+
+
 @router.get("/scan/status")
 async def get_scan_status(db: AsyncSession = Depends(get_db)):
     """Get current scan status"""
diff --git a/frontend/src/components/layout/LeftSidebar.tsx b/frontend/src/components/layout/LeftSidebar.tsx
index ba3363c..ca4d6c8 100644
--- a/frontend/src/components/layout/LeftSidebar.tsx
+++ b/frontend/src/components/layout/LeftSidebar.tsx
@@ -16,10 +16,12 @@ import clsx from 'clsx'
 import { AddSourceFolderDialog } from '../dialogs/AddSourceFolderDialog'
 import { sourceFolders, library, photos as photosApi } from '../../services/api'
 import { useQuery, useMutation, useQueryClient } from '@tanstack/react-query'
+import { format } from 'date-fns'
 import { toast } from '../ToastContainer'
 import { useFilterStore } from '../../store/filterStore'
 import { HeapsPanel } from '../heaps/HeapsPanel'
 import { PHOTO_DRAG_MIME } from '../timeline/PhotoThumbnail'
+import { useDateBucketsQuery } from '../../hooks/useDateBucketsQuery'
 
 interface TreeItem {
   id: string
@@ -41,7 +43,12 @@ export function LeftSidebar() {
   const setRatingMin = useFilterStore((s) => s.setRatingMin)
   const setFlag = useFilterStore((s) => s.setFlag)
   const setFolderId = useFilterStore((s) => s.setFolderId)
+  const setDateFrom = useFilterStore((s) => s.setDateFrom)
+  const setDateTo = useFilterStore((s) => s.setDateTo)
   const filterFolderId = useFilterStore((s) => s.folderId)
+  const filterDateFrom = useFilterStore((s) => s.dateFrom)
+  const filterDateTo = useFilterStore((s) => s.dateTo)
+  const { data: dateBuckets = [] } = useDateBucketsQuery()
   const [dropTargetId, setDropTargetId] = useState<string | null>(null)
 
   // Bulk discard mutation for the drag-onto-Discarded interaction.
@@ -115,6 +122,26 @@ export function LeftSidebar() {
           const folderId = id.slice('folder-'.length)
           clearAllFilters()
           setFolderId(folderId)
+        } else if (id.startsWith('date-year-')) {
+          const year = parseInt(id.slice('date-year-'.length), 10)
+          if (Number.isFinite(year)) {
+            clearAllFilters()
+            setDateFrom(`${year}-01-01`)
+            setDateTo(`${year}-12-31`)
+          }
+        } else if (id.startsWith('date-month-')) {
+          // Format: date-month-YYYY-MM
+          const parts = id.slice('date-month-'.length).split('-')
+          const year = parseInt(parts[0], 10)
+          const month = parseInt(parts[1], 10)
+          if (Number.isFinite(year) && Number.isFinite(month)) {
+            const lastDay = new Date(year, month, 0).getDate()
+            const mm = String(month).padStart(2, '0')
+            const dd = String(lastDay).padStart(2, '0')
+            clearAllFilters()
+            setDateFrom(`${year}-${mm}-01`)
+            setDateTo(`${year}-${mm}-${dd}`)
+          }
         }
     }
   }
@@ -184,6 +211,22 @@ export function LeftSidebar() {
     setExpandedItems(newExpanded)
   }
   
+  // Build the dynamic By Date subtree from the date_buckets aggregation.
+  // Year nodes contain month nodes; clicking either sets the date range
+  // filter (handled in applyLibraryNode). Sorted newest-first by the
+  // backend already.
+  const byDateChildren: TreeItem[] = dateBuckets.map((year) => ({
+    id: `date-year-${year.year}`,
+    label: String(year.year),
+    icon: <Calendar className="h-4 w-4" />,
+    count: year.count,
+    children: year.months.map((m) => ({
+      id: `date-month-${year.year}-${m.month}`,
+      label: format(new Date(year.year, m.month - 1, 1), 'MMMM'),
+      count: m.count,
+    })),
+  }))
+
   const libraryTree: TreeItem[] = [
     {
       id: 'library',
@@ -191,7 +234,12 @@ export function LeftSidebar() {
       icon: <HardDrive className="h-4 w-4" />,
       children: [
         { id: 'all-photos', label: 'All Photos', icon: <Image className="h-4 w-4" />, count: 0 },
-        { id: 'by-date', label: 'By Date', icon: <Calendar className="h-4 w-4" /> },
+        {
+          id: 'by-date',
+          label: 'By Date',
+          icon: <Calendar className="h-4 w-4" />,
+          children: byDateChildren,
+        },
         { id: 'rated', label: 'Rated', icon: <Star className="h-4 w-4" />, count: 0 },
         { id: 'discarded', label: 'Discarded', icon: <Trash2 className="h-4 w-4" />, count: 0 },
       ],
@@ -213,7 +261,7 @@ export function LeftSidebar() {
   // Derive whether a tree item is currently the "active" filter target.
   // Folder rows are selected when the filter store's folderId matches; the
   // library "All Photos" virtual node is selected when no folder/heap filter
-  // is set.
+  // is set; year/month nodes when their date range matches.
   const isItemActive = (id: string): boolean => {
     if (id.startsWith('folder-')) {
       return filterFolderId === id.slice('folder-'.length)
@@ -221,6 +269,18 @@ export function LeftSidebar() {
     if (id === 'all-photos') {
       return filterFolderId === null && selectedItem === 'all-photos'
     }
+    if (id.startsWith('date-year-')) {
+      const year = id.slice('date-year-'.length)
+      return filterDateFrom === `${year}-01-01` && filterDateTo === `${year}-12-31`
+    }
+    if (id.startsWith('date-month-')) {
+      const parts = id.slice('date-month-'.length).split('-')
+      const year = parseInt(parts[0], 10)
+      const month = parseInt(parts[1], 10)
+      if (!Number.isFinite(year) || !Number.isFinite(month)) return false
+      const mm = String(month).padStart(2, '0')
+      return filterDateFrom === `${year}-${mm}-01` && filterDateTo?.startsWith(`${year}-${mm}-`) === true
+    }
     return selectedItem === id
   }
 
diff --git a/frontend/src/hooks/useDateBucketsQuery.ts b/frontend/src/hooks/useDateBucketsQuery.ts
new file mode 100644
index 0000000..b2281b4
--- /dev/null
+++ b/frontend/src/hooks/useDateBucketsQuery.ts
@@ -0,0 +1,12 @@
+import { useQuery } from '@tanstack/react-query'
+import { library, type DateBucketYear } from '../services/api'
+
+export const DATE_BUCKETS_QUERY_KEY = ['library', 'date_buckets'] as const
+
+export function useDateBucketsQuery() {
+  return useQuery<DateBucketYear[]>({
+    queryKey: DATE_BUCKETS_QUERY_KEY,
+    queryFn: library.dateBuckets,
+    staleTime: 60_000,
+  })
+}
diff --git a/frontend/src/services/api.ts b/frontend/src/services/api.ts
index b534b58..d70610d 100644
--- a/frontend/src/services/api.ts
+++ b/frontend/src/services/api.ts
@@ -113,6 +113,16 @@ export const photos = {
 }
 
 // Library API
+export interface DateBucketMonth {
+  month: number
+  count: number
+}
+export interface DateBucketYear {
+  year: number
+  count: number
+  months: DateBucketMonth[]
+}
+
 export const library = {
   scan: async () => {
     const response = await api.post('/library/scan')
@@ -128,6 +138,12 @@ export const library = {
     const response = await api.get('/library/stats')
     return response.data
   },
+
+  /** Year/month aggregation for the sidebar By Date drilldown. */
+  dateBuckets: async (): Promise<DateBucketYear[]> => {
+    const response = await api.get('/library/date_buckets')
+    return response.data
+  },
 }
 
 // Heaps API