diff --git a/package-lock.json b/package-lock.json
index 98488b1673..748fb49e26 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -46247,6 +46247,7 @@
         "@instructure/ui-icons": "9.0.1",
         "@instructure/ui-prop-types": "9.0.1",
         "@instructure/ui-react-utils": "9.0.1",
+        "@instructure/ui-simple-select": "9.0.1",
         "@instructure/ui-testable": "9.0.1",
         "@instructure/ui-utils": "9.0.1",
         "@instructure/ui-view": "9.0.1",
diff --git a/packages/shared-types/src/ComponentThemeVariables.ts b/packages/shared-types/src/ComponentThemeVariables.ts
index 58e8840103..e787504a00 100644
--- a/packages/shared-types/src/ComponentThemeVariables.ts
+++ b/packages/shared-types/src/ComponentThemeVariables.ts
@@ -283,6 +283,8 @@ export type CalendarTheme = {
   color: Colors['textDarkest']
   background: Colors['backgroundLightest']
   navMargin: Spacing['small']
+  navWithYearMargin: Spacing['xSmall']
+  yearPickerMargin: Spacing['mediumSmall']
   maxHeaderWidth: Spacing['medium']
 }
 
diff --git a/packages/ui-calendar/package.json b/packages/ui-calendar/package.json
index c20e6f00ba..dfadabb979 100644
--- a/packages/ui-calendar/package.json
+++ b/packages/ui-calendar/package.json
@@ -45,6 +45,7 @@
     "@instructure/ui-testable": "9.0.1",
     "@instructure/ui-utils": "9.0.1",
     "@instructure/ui-view": "9.0.1",
+    "@instructure/ui-simple-select": "9.0.1",
     "@instructure/uid": "9.0.1",
     "prop-types": "^15.8.1"
   },
diff --git a/packages/ui-calendar/src/Calendar/README.md b/packages/ui-calendar/src/Calendar/README.md
index ed7a26c653..f11810fd17 100644
--- a/packages/ui-calendar/src/Calendar/README.md
+++ b/packages/ui-calendar/src/Calendar/README.md
@@ -48,6 +48,43 @@ class Example extends React.Component {
 render(<Example />)
 ```
 
+### With year picker
+
+```js
+---
+type: example
+---
+class Example extends React.Component {
+  state = {
+      selectedDate: "",
+      visibleMonth:"2024-02"
+    }
+
+  setVisibleMonth = () => {
+    this.setState({visibleMonth: "2028-09"})
+  }
+  render = () =>
+<Calendar
+  visibleMonth={this.state.visibleMonth}
+  currentDate="2024-02-29"
+  disabledDates={['2023-12-22', '2023-12-12', '2023-12-11']}
+  selectedDate={this.state.selectedDate}
+  onRequestRenderNextMonth={(_e, requestedMonth) => this.setState({visibleMonth: requestedMonth})}
+  onRequestRenderPrevMonth={(_e, requestedMonth) => this.setState({visibleMonth: requestedMonth})}
+  onDateSelected={(date)=>{
+    this.setState({selectedDate: date})
+  }}
+  withYearPicker={{
+    screenReaderLabel: "Year picker",
+    startYear:1999,
+
+    maxHeight: "200px"
+  }}
+/>
+}
+render(<Example />)
+```
+
 ### Composing a Calendar in your Application
 
 By design, the `Calendar` component does not dictate which date libraries or
diff --git a/packages/ui-calendar/src/Calendar/index.tsx b/packages/ui-calendar/src/Calendar/index.tsx
index 4ff0038b56..08abcfc3d2 100644
--- a/packages/ui-calendar/src/Calendar/index.tsx
+++ b/packages/ui-calendar/src/Calendar/index.tsx
@@ -58,6 +58,8 @@ import {
   IconArrowOpenEndSolid
 } from '@instructure/ui-icons'
 
+import { SimpleSelect } from '@instructure/ui-simple-select'
+
 /**
 ---
 category: components
@@ -197,9 +199,21 @@ class Calendar extends Component<CalendarProps, CalendarState> {
     this.setState({ visibleMonth: newDate })
   }
 
-  renderHeader() {
-    const { renderNavigationLabel, styles } = this.props
+  handleYearChange = (e: React.MouseEvent, year: number) => {
+    const { withYearPicker } = this.props
     const { visibleMonth } = this.state
+    const newDate = visibleMonth.clone()
+    if (withYearPicker?.onRequestYearChange) {
+      withYearPicker.onRequestYearChange(e, year)
+      return
+    }
+    newDate.year(year)
+    this.setState({ visibleMonth: newDate })
+  }
+
+  renderHeader() {
+    const { renderNavigationLabel, styles, withYearPicker } = this.props
+    const { visibleMonth, today } = this.state
     const { prevButton, nextButton } = this.renderMonthNavigationButtons()
 
     const cloneButton = (
@@ -218,18 +232,64 @@ class Calendar extends Component<CalendarProps, CalendarState> {
       ...(prevButton || nextButton ? [styles?.navigationWithButtons] : [])
     ]
 
+    let yearList: number[] = []
+
+    if (withYearPicker) {
+      const { startYear, endYear, years } = withYearPicker
+      if (years) {
+        yearList = years
+      } else {
+        if (!startYear) {
+          console.warn(
+            'You need to provide at least `startYear` or `years` in `withYearPicker`'
+          )
+        }
+
+        const years = endYear || today.year()
+        for (let year = years; year >= startYear!; year--) {
+          yearList.push(year)
+        }
+      }
+    }
+
     return (
-      <div css={style}>
-        {prevButton && cloneButton(prevButton, this.handleMonthChange('prev'))}
-        {renderNavigationLabel ? (
-          callRenderProp(renderNavigationLabel)
-        ) : (
-          <span>
-            <div>{visibleMonth.format('MMMM')}</div>
-            <div>{visibleMonth.format('YYYY')}</div>
-          </span>
-        )}
-        {nextButton && cloneButton(nextButton, this.handleMonthChange('next'))}
+      <div>
+        <div css={style}>
+          {prevButton &&
+            cloneButton(prevButton, this.handleMonthChange('prev'))}
+          {renderNavigationLabel ? (
+            callRenderProp(renderNavigationLabel)
+          ) : (
+            <span>
+              <div>{visibleMonth.format('MMMM')}</div>
+              {!withYearPicker ? (
+                <div>{visibleMonth.format('YYYY')}</div>
+              ) : null}
+            </span>
+          )}
+          {nextButton &&
+            cloneButton(nextButton, this.handleMonthChange('next'))}
+        </div>
+
+        {withYearPicker ? (
+          <div css={styles?.yearPicker}>
+            <SimpleSelect
+              width="90px"
+              renderLabel=""
+              assistiveText={withYearPicker.screenReaderLabel}
+              value={Number(visibleMonth.format('YYYY'))}
+              onChange={(e: any, { value }: any) =>
+                this.handleYearChange(e, Number(value))
+              }
+            >
+              {yearList.map((year) => (
+                <SimpleSelect.Option key={year} id={`opt-${year}`} value={year}>
+                  {`${year}`}
+                </SimpleSelect.Option>
+              ))}
+            </SimpleSelect>
+          </div>
+        ) : null}
       </div>
     )
   }
diff --git a/packages/ui-calendar/src/Calendar/props.ts b/packages/ui-calendar/src/Calendar/props.ts
index c0f51f2b30..38b190fa01 100644
--- a/packages/ui-calendar/src/Calendar/props.ts
+++ b/packages/ui-calendar/src/Calendar/props.ts
@@ -152,6 +152,30 @@ type CalendarOwnProps = {
    * Visible month for the rendered calendar. Formatted as an ISO date string.
    */
   visibleMonth?: string
+
+  /**
+   * If set, years can be picked from a dropdown.
+   * It accepts an object.
+   * screenReaderLabel: string // e.g.: i18n("pick a year")
+   *
+   * maxHeight?: string // e.g.: 200px, Defaults to 300px. Sets the dropdown max height
+   *
+   * onRequestYearChange?:(e: React.MouseEvent,requestedYear: number): void // if set, on year change, only this will be called and no internal change will take place
+   *
+   * startYear?: number // e.g.: 2001, sets the start year of the selectable list
+   *
+   * endYear?: number // e.g.: 2030, sets the end year of the selectable list. If not provided with startYear, it'll default to the currentDate's year
+   *
+   * years?: number[] // e.g.: [2001,2002,2003,2010], if set, startYear and endYear will be ignored and this list will be used as selectable list
+   */
+  withYearPicker?: {
+    screenReaderLabel: string
+    maxHeight?: string
+    onRequestYearChange?: (e: any, requestedYear: number) => void
+    startYear?: number
+    endYear?: number
+    years?: never
+  }
 }
 
 type PropKeys = keyof CalendarOwnProps
@@ -163,7 +187,7 @@ type CalendarProps = CalendarOwnProps &
   OtherHTMLAttributes<CalendarOwnProps>
 
 type CalendarStyle = ComponentStyle<
-  'navigation' | 'navigationWithButtons' | 'weekdayHeader'
+  'navigation' | 'navigationWithButtons' | 'weekdayHeader' | 'yearPicker'
 >
 
 const propTypes: PropValidators<PropKeys> = {
@@ -184,7 +208,8 @@ const propTypes: PropValidators<PropKeys> = {
   role: PropTypes.oneOf(['table', 'listbox']),
   selectedDate: PropTypes.string,
   timezone: PropTypes.string,
-  visibleMonth: PropTypes.string
+  visibleMonth: PropTypes.string,
+  withYearPicker: PropTypes.object
 }
 
 const allowedProps: AllowedPropKeys = [
diff --git a/packages/ui-calendar/src/Calendar/styles.ts b/packages/ui-calendar/src/Calendar/styles.ts
index ff63c50d95..3d6e25d4ed 100644
--- a/packages/ui-calendar/src/Calendar/styles.ts
+++ b/packages/ui-calendar/src/Calendar/styles.ts
@@ -23,7 +23,7 @@
  */
 
 import type { CalendarTheme } from '@instructure/shared-types'
-import type { CalendarStyle } from './props'
+import type { CalendarStyle, CalendarProps } from './props'
 
 /**
  * ---
@@ -33,7 +33,11 @@ import type { CalendarStyle } from './props'
  * @param  {Object} componentTheme The theme variable object.
  * @return {Object} The final style object, which will be used in the component
  */
-const generateStyle = (componentTheme: CalendarTheme): CalendarStyle => {
+const generateStyle = (
+  componentTheme: CalendarTheme,
+  props: CalendarProps
+): CalendarStyle => {
+  const { withYearPicker } = props
   return {
     navigation: {
       label: 'calendar__navigation',
@@ -43,7 +47,9 @@ const generateStyle = (componentTheme: CalendarTheme): CalendarStyle => {
       fontFamily: componentTheme.fontFamily,
       fontSize: componentTheme.fontSize,
       fontWeight: componentTheme.fontWeight,
-      marginBottom: componentTheme.navMargin
+      marginBottom: withYearPicker
+        ? componentTheme.navWithYearMargin
+        : componentTheme.navMargin
     },
     navigationWithButtons: {
       label: 'calendar__navigation--withButtons',
@@ -55,6 +61,12 @@ const generateStyle = (componentTheme: CalendarTheme): CalendarStyle => {
       label: 'calendar__weekdayHeader',
       textAlign: 'center',
       maxWidth: componentTheme.maxHeaderWidth
+    },
+    yearPicker: {
+      display: 'flex',
+      justifyContent: 'center',
+      alignItems: 'center',
+      marginBottom: componentTheme.yearPickerMargin
     }
   }
 }
diff --git a/packages/ui-calendar/src/Calendar/theme.ts b/packages/ui-calendar/src/Calendar/theme.ts
index c841af95bf..33e70b413c 100644
--- a/packages/ui-calendar/src/Calendar/theme.ts
+++ b/packages/ui-calendar/src/Calendar/theme.ts
@@ -48,6 +48,8 @@ const generateComponentTheme = (theme: Theme): CalendarTheme => {
     background: colors?.backgroundLightest,
 
     navMargin: spacing?.small,
+    navWithYearMargin: spacing?.xSmall,
+    yearPickerMargin: spacing?.mediumSmall,
 
     maxHeaderWidth: spacing?.medium
   }
diff --git a/packages/ui-calendar/tsconfig.build.json b/packages/ui-calendar/tsconfig.build.json
index f2ab0cb9bf..ff8dae0706 100644
--- a/packages/ui-calendar/tsconfig.build.json
+++ b/packages/ui-calendar/tsconfig.build.json
@@ -60,6 +60,9 @@
     },
     {
       "path": "../ui-icons/tsconfig.build.json"
+    },
+    {
+      "path": "../ui-simple-select/tsconfig.build.json"
     }
   ]
 }
diff --git a/packages/ui-select/src/Select/index.tsx b/packages/ui-select/src/Select/index.tsx
index 6830ed0bfa..9429a35415 100644
--- a/packages/ui-select/src/Select/index.tsx
+++ b/packages/ui-select/src/Select/index.tsx
@@ -149,7 +149,7 @@ class Select extends Component<SelectProps> {
     placement: 'bottom stretch',
     constrain: 'window',
     shouldNotWrap: false,
-    scrollToHighlightedOption: false
+    scrollToHighlightedOption: true
   }
 
   static Option = Option