diff --git a/site/src/app/roadmap/catalog/ProgramRequirementsList.scss b/site/src/app/roadmap/catalog/ProgramRequirementsList.scss
index d391523d1..d49488b26 100644
--- a/site/src/app/roadmap/catalog/ProgramRequirementsList.scss
+++ b/site/src/app/roadmap/catalog/ProgramRequirementsList.scss
@@ -214,6 +214,14 @@
     color: inherit;
   }
 
+  &.quarter-filter-dimmed {
+    opacity: 0.35;
+
+    a {
+      text-decoration: line-through;
+    }
+  }
+
   &.completed {
     background-color: var(--mui-palette-overlay-overlay2);
     outline: 1.5px solid var(--mui-palette-text-secondary);
diff --git a/site/src/app/roadmap/catalog/ProgramRequirementsList.tsx b/site/src/app/roadmap/catalog/ProgramRequirementsList.tsx
index a0a92ec49..cc870689d 100644
--- a/site/src/app/roadmap/catalog/ProgramRequirementsList.tsx
+++ b/site/src/app/roadmap/catalog/ProgramRequirementsList.tsx
@@ -1,5 +1,5 @@
 import './ProgramRequirementsList.scss';
-import React, { FC, useCallback, useEffect, useState } from 'react';
+import React, { createContext, FC, useCallback, useContext, useEffect, useRef, useState } from 'react';
 import { Button, Dialog, DialogActions, DialogContent, DialogContentText, DialogTitle } from '@mui/material';
 import {
   COMPLETE_ALL_TEXT,
@@ -40,12 +40,27 @@ import { useTransferredCredits, TransferredCourseWithType } from '../../../hooks
 import { useIsLoggedIn } from '../../../hooks/isLoggedIn';
 import SwapHorizOutlinedIcon from '@mui/icons-material/SwapHorizOutlined';
 import { Badge, Checkbox, Collapse } from '@mui/material';
+import { courseMatchesQuarterFilter } from '../../../helpers/quarterFilter';
 import { ExpandMore } from '../../../component/ExpandMore/ExpandMore';
 import SwapHorizIcon from '@mui/icons-material/SwapHoriz';
 import MenuTile from '../transfers/MenuTile';
 import { setShowMobileCreditsMenu } from '../../../store/slices/transferCreditsSlice';
 import ClickableDiv from '../../../component/ClickableDiv/ClickableDiv';
 
+const CourseTermsContext = createContext<Record<string, string[]>>({});
+
+function collectCourseIDs(requirements: ProgramRequirement[]): string[] {
+  const ids: string[] = [];
+  for (const req of requirements) {
+    if (req.requirementType === 'Course' || req.requirementType === 'Unit') {
+      ids.push(...req.courses);
+    } else if (req.requirementType === 'Group') {
+      ids.push(...collectCourseIDs(req.requirements));
+    }
+  }
+  return ids;
+}
+
 interface SourceOverlayProps {
   completedBy: TransferredCourseWithType['transferType'] | 'roadmap' | null;
 }
@@ -67,11 +82,14 @@ interface CourseTileProps {
   dragTimestamp?: number;
 }
 const CourseTile: FC<CourseTileProps> = ({ courseID, completedBy, dragTimestamp = 0 }) => {
+  const courseTermsMap = useContext(CourseTermsContext);
+  const terms = courseTermsMap[courseID];
   const [courseData, setCourseData] = useState<string | CourseGQLData>(courseID);
   const [loading, setLoading] = useState(false);
   const isMobile = useIsMobile();
   const clearedCourses = useClearedCourses();
   const dispatch = useAppDispatch();
+  const quarterFilters = useAppSelector((state) => state.filters.quarterFilters);
 
   const loadFullData = useCallback(async () => {
     if (typeof courseData !== 'string') return courseData;
@@ -109,7 +127,9 @@ const CourseTile: FC<CourseTileProps> = ({ courseID, completedBy, dragTimestamp
 
   const tapProps = { onClick: insertCourseOnClick, role: 'button', tabIndex: 0 };
   const tappableCourseProps = isMobile ? tapProps : {};
-  const className = `program-course-tile${isMobile ? ' mobile' : ''}${loading ? ' loading' : ''}${completedBy ? ' completed' : ''}`;
+  const isDimmed =
+    quarterFilters.length > 0 && terms !== undefined && !courseMatchesQuarterFilter(terms, quarterFilters);
+  const className = `program-course-tile${isMobile ? ' mobile' : ''}${loading ? ' loading' : ''}${completedBy ? ' completed' : ''}${isDimmed ? ' quarter-filter-dimmed' : ''}`;
   let fontSize: string | undefined;
 
   if (courseID.length > 10) {
@@ -550,6 +570,22 @@ const ProgramRequirementsList: FC<RequireCourseListProps> = ({
 }) => {
   const formattedRequirements = formatRequirements(requirements, skipCollapseSingletons);
   const transferredCourses = useTransferredCredits().courses;
+
+  const [courseTermsMap, setCourseTermsMap] = useState<Record<string, string[]>>({});
+  const fetchedIDs = useRef<Set<string>>(new Set());
+  useEffect(() => {
+    const allCourseIDs = collectCourseIDs(requirements);
+    const uncached = allCourseIDs.filter((id) => !fetchedIDs.current.has(id));
+    if (uncached.length === 0) return;
+    uncached.forEach((id) => fetchedIDs.current.add(id));
+    trpc.courses.batch.mutate({ courses: uncached }).then((data) => {
+      setCourseTermsMap((prev) => {
+        const next = { ...prev };
+        for (const [id, course] of Object.entries(data)) next[id] = course.terms;
+        return next;
+      });
+    });
+  }, [requirements]);
   const roadmapPlans = useAppSelector((state) => state.roadmap.plans);
   const roadmapPlanIndex = useAppSelector((state) => state.roadmap.currentPlanIndex);
   const yearPlans = roadmapPlans[roadmapPlanIndex].content.yearPlans;
@@ -571,17 +607,19 @@ const ProgramRequirementsList: FC<RequireCourseListProps> = ({
   );
 
   return (
-    <div className="program-requirements">
-      {/* key is ok because we don't reorder these */}
-      {formattedRequirements.map((r, i) => (
-        <ProgramRequirementDisplay
-          requirement={r}
-          key={i}
-          storeKey={`${storeKeyPrefix}-${i}`}
-          takenCourseIDs={takenCourseSet}
-        />
-      ))}
-    </div>
+    <CourseTermsContext.Provider value={courseTermsMap}>
+      <div className="program-requirements">
+        {/* key is ok because we don't reorder these */}
+        {formattedRequirements.map((r, i) => (
+          <ProgramRequirementDisplay
+            requirement={r}
+            key={i}
+            storeKey={`${storeKeyPrefix}-${i}`}
+            takenCourseIDs={takenCourseSet}
+          />
+        ))}
+      </div>
+    </CourseTermsContext.Provider>
   );
 };
 
diff --git a/site/src/app/roadmap/planner/Course.scss b/site/src/app/roadmap/planner/Course.scss
index 7d85d7a23..37da5ac25 100644
--- a/site/src/app/roadmap/planner/Course.scss
+++ b/site/src/app/roadmap/planner/Course.scss
@@ -154,6 +154,14 @@
   }
 }
 
+.course.course-dimmed {
+  opacity: 0.4;
+
+  .name {
+    text-decoration: line-through;
+  }
+}
+
 .course.sortable-fallback {
   height: fit-content !important;
   animation: course-fade-in 0.2s forwards;
diff --git a/site/src/app/roadmap/planner/Course.tsx b/site/src/app/roadmap/planner/Course.tsx
index 00fcfd857..7c77f7178 100644
--- a/site/src/app/roadmap/planner/Course.tsx
+++ b/site/src/app/roadmap/planner/Course.tsx
@@ -80,11 +80,12 @@ interface CourseProps {
   addMode?: 'tap' | 'drag';
   data: PlannerCourseData;
   onSetVariableUnits?: (units: number | undefined) => void;
+  dimmed?: boolean;
 }
 
 const Course: FC<CourseProps> = (props) => {
   const { title, courseLevel, minUnits, maxUnits, terms, geList, userChosenUnits } = props.data;
-  const { requiredCourses, quarterMismatch, onDelete, openPopoverLeft, onSetVariableUnits } = props;
+  const { requiredCourses, quarterMismatch, onDelete, openPopoverLeft, onSetVariableUnits, dimmed } = props;
 
   const isInRoadmap = !!onDelete;
   const isMobile = useIsMobile();
@@ -115,7 +116,10 @@ const Course: FC<CourseProps> = (props) => {
   }, [userChosenUnits]);
 
   return (
-    <div className={`course ${isInRoadmap ? 'roadmap-course' : ''}`} {...tappableCourseProps}>
+    <div
+      className={`course ${isInRoadmap ? 'roadmap-course' : ''}${dimmed ? ' course-dimmed' : ''}`}
+      {...tappableCourseProps}
+    >
       {(!isMobile || isInRoadmap) && (
         <div className="course-drag-handle">
           <DragIndicatorIcon />
diff --git a/site/src/app/roadmap/search/SavedAndSearch.tsx b/site/src/app/roadmap/search/SavedAndSearch.tsx
index 385a439fa..735564488 100644
--- a/site/src/app/roadmap/search/SavedAndSearch.tsx
+++ b/site/src/app/roadmap/search/SavedAndSearch.tsx
@@ -10,6 +10,7 @@ import { ReactSortable, SortableEvent } from 'react-sortablejs';
 import { setActiveCourse } from '../../../store/slices/roadmapSlice';
 import { getMissingPrerequisites } from '../../../helpers/planner';
 import { courseSearchSortable } from '../../../helpers/sortable';
+import { courseMatchesQuarterFilter } from '../../../helpers/quarterFilter';
 import Course from '../planner/Course';
 import LoadingSpinner from '../../../component/LoadingSpinner/LoadingSpinner';
 import NoResults from '../../../component/NoResults/NoResults';
@@ -49,6 +50,7 @@ const CourseResultItem: FC<{ course: CourseGQLData; addMode: 'tap' | 'drag' }> =
   const courseId = `${course.department} ${course.courseNumber}`;
   const clearedCourses = useClearedCoursesUntil(courseId);
   const coursesInCurrentQuarter = useGetCoursesInSameQuarter(courseId);
+  const quarterFilters = useAppSelector((state) => state.filters.quarterFilters);
 
   const missingPrerequisites = getMissingPrerequisites(
     clearedCourses,
@@ -56,7 +58,9 @@ const CourseResultItem: FC<{ course: CourseGQLData; addMode: 'tap' | 'drag' }> =
     coursesInCurrentQuarter,
   );
 
-  return <Course data={course} addMode={addMode} requiredCourses={missingPrerequisites} />;
+  const isDimmed = quarterFilters.length > 0 && !courseMatchesQuarterFilter(course.terms, quarterFilters);
+
+  return <Course data={course} addMode={addMode} requiredCourses={missingPrerequisites} dimmed={isDimmed} />;
 };
 
 const CourseResultsContainer: FC<CourseResultsContainerProps> = ({ searchResults }) => {
diff --git a/site/src/app/roadmap/sidebar/DesktopRoadmapSidebar.scss b/site/src/app/roadmap/sidebar/DesktopRoadmapSidebar.scss
index 37fd5f937..c8e62ac41 100644
--- a/site/src/app/roadmap/sidebar/DesktopRoadmapSidebar.scss
+++ b/site/src/app/roadmap/sidebar/DesktopRoadmapSidebar.scss
@@ -3,13 +3,15 @@
 .roadmap-sidebar {
   background-color: var(--mui-palette-overlay-overlay1);
   height: 100%;
-  overflow: auto;
+  overflow: hidden;
   width: globals.$roadmap-sidebar-width;
   flex-shrink: 0;
   padding-top: globals.$roadmap-toolbar-height;
   position: relative;
   border-right: 1px solid var(--mui-palette-divider);
   z-index: 50;
+  display: flex;
+  flex-direction: column;
 
   .sidebar-tabs {
     position: absolute;
@@ -26,7 +28,7 @@
   }
 
   .sidebar-content {
-    height: 100%;
+    flex: 1;
     overflow: auto;
     padding: 16px 20px;
 
diff --git a/site/src/app/roadmap/sidebar/DesktopRoadmapSidebar.tsx b/site/src/app/roadmap/sidebar/DesktopRoadmapSidebar.tsx
index 0adbaa8e3..7b42a0f2d 100644
--- a/site/src/app/roadmap/sidebar/DesktopRoadmapSidebar.tsx
+++ b/site/src/app/roadmap/sidebar/DesktopRoadmapSidebar.tsx
@@ -13,6 +13,7 @@ import { useHasUnreadTransfers } from '../../../hooks/transferCredits';
 import { useAppDispatch, useAppSelector } from '../../../store/hooks';
 import { clearUnreadTransfers } from '../../../store/slices/transferCreditsSlice';
 import { setSelectedSidebarTab } from '../../../store/slices/roadmapSlice';
+import QuarterFilterBar from '../../../component/QuarterFilterBar/QuarterFilterBar';
 
 const DesktopRoadmapSidebar = () => {
   const selectedIndex = useAppSelector((state) => state.roadmap.selectedSidebarTab);
@@ -50,6 +51,7 @@ const DesktopRoadmapSidebar = () => {
         <Tab icon={<SearchIcon />} iconPosition="start" label="Search" />
       </Tabs>
 
+      {(selectedIndex === 1 || selectedIndex === 2) && <QuarterFilterBar />}
       <div className="sidebar-content" id="sidebarScrollContainer">
         {selectedIndex === 0 && <TransferCreditsMenu />}
         {selectedIndex === 1 && <CourseCatalog />}
diff --git a/site/src/component/QuarterFilterBar/QuarterFilterBar.scss b/site/src/component/QuarterFilterBar/QuarterFilterBar.scss
new file mode 100644
index 000000000..245d18d12
--- /dev/null
+++ b/site/src/component/QuarterFilterBar/QuarterFilterBar.scss
@@ -0,0 +1,43 @@
+.quarter-filter-bar {
+  display: flex;
+  align-items: center;
+  justify-content: space-evenly;
+  gap: 6px;
+  padding: 6px 12px;
+  border-bottom: 1px solid var(--mui-palette-divider);
+  background-color: var(--mui-palette-background-paper);
+  flex-shrink: 0;
+
+  .quarter-filter-btn {
+    display: flex;
+    align-items: center;
+    gap: 4px;
+    padding: 4px 10px;
+    border: 1px solid var(--mui-palette-divider);
+    border-radius: 16px;
+    background: transparent;
+    cursor: pointer;
+    font-size: 13px;
+    color: var(--mui-palette-text-secondary);
+    transition:
+      background-color 0.15s,
+      color 0.15s,
+      border-color 0.15s;
+    white-space: nowrap;
+
+    &:hover {
+      background-color: var(--mui-palette-action-hover);
+    }
+
+    &.active {
+      background-color: var(--mui-palette-primary-main);
+      color: var(--mui-palette-primary-contrastText);
+      border-color: var(--mui-palette-primary-main);
+    }
+
+    .quarter-emoji {
+      font-size: 15px;
+      line-height: 1;
+    }
+  }
+}
diff --git a/site/src/component/QuarterFilterBar/QuarterFilterBar.tsx b/site/src/component/QuarterFilterBar/QuarterFilterBar.tsx
new file mode 100644
index 000000000..3b43b9859
--- /dev/null
+++ b/site/src/component/QuarterFilterBar/QuarterFilterBar.tsx
@@ -0,0 +1,36 @@
+'use client';
+import './QuarterFilterBar.scss';
+import { FC } from 'react';
+import { useAppDispatch, useAppSelector } from '../../store/hooks';
+import { QuarterFilterName } from '../../helpers/quarterFilter';
+import { toggleQuarterFilter } from '../../store/slices/filtersSlice';
+
+const QUARTERS: { name: QuarterFilterName; emoji: string }[] = [
+  { name: 'Fall', emoji: '🍂' },
+  { name: 'Winter', emoji: '❄️' },
+  { name: 'Spring', emoji: '🌸' },
+  { name: 'Summer', emoji: '☀️' },
+];
+
+const QuarterFilterBar: FC = () => {
+  const dispatch = useAppDispatch();
+  const quarterFilters = useAppSelector((state) => state.filters.quarterFilters);
+
+  return (
+    <div className="quarter-filter-bar">
+      {QUARTERS.map(({ name, emoji }) => (
+        <button
+          key={name}
+          className={`quarter-filter-btn${quarterFilters.includes(name) ? ' active' : ''}`}
+          onClick={() => dispatch(toggleQuarterFilter(name))}
+          title={`Filter by ${name}`}
+        >
+          <span className="quarter-emoji">{emoji}</span>
+          <span className="quarter-name">{name}</span>
+        </button>
+      ))}
+    </div>
+  );
+};
+
+export default QuarterFilterBar;
diff --git a/site/src/helpers/quarterFilter.ts b/site/src/helpers/quarterFilter.ts
new file mode 100644
index 000000000..eb135b02b
--- /dev/null
+++ b/site/src/helpers/quarterFilter.ts
@@ -0,0 +1,33 @@
+export type QuarterFilterName = 'Fall' | 'Winter' | 'Spring' | 'Summer';
+
+const searchPrevYears = 2;
+
+function quarterOfferedRecently(terms: string[], quarter: QuarterFilterName): boolean {
+  const currentDate = new Date();
+  const currentStartYear = currentDate.getMonth() >= 8 ? currentDate.getFullYear() : currentDate.getFullYear() - 1;
+  const termYear = quarter === 'Fall' ? currentStartYear : currentStartYear + 1;
+
+  for (let i = 0; i <= searchPrevYears; i++) {
+    const year = termYear - i;
+    if (quarter === 'Summer') {
+      if (
+        terms.includes(`${year} Summer10wk`) ||
+        terms.includes(`${year} Summer1`) ||
+        terms.includes(`${year} Summer2`)
+      ) {
+        return true;
+      }
+    } else {
+      if (terms.includes(`${year} ${quarter}`)) {
+        return true;
+      }
+    }
+  }
+  return false;
+}
+
+export function courseMatchesQuarterFilter(terms: string[], quarterFilters: QuarterFilterName[]): boolean {
+  if (quarterFilters.length === 0) return true;
+  if (terms.length === 0) return false;
+  return quarterFilters.some((filter) => quarterOfferedRecently(terms, filter));
+}
diff --git a/site/src/store/slices/filtersSlice.ts b/site/src/store/slices/filtersSlice.ts
new file mode 100644
index 000000000..9566bf977
--- /dev/null
+++ b/site/src/store/slices/filtersSlice.ts
@@ -0,0 +1,24 @@
+import { createSlice, PayloadAction } from '@reduxjs/toolkit';
+import { QuarterFilterName } from '../../helpers/quarterFilter';
+
+export const filtersSlice = createSlice({
+  name: 'filters',
+  initialState: {
+    quarterFilters: [] as QuarterFilterName[],
+  },
+  reducers: {
+    toggleQuarterFilter: (state, action: PayloadAction<QuarterFilterName>) => {
+      const quarter = action.payload;
+      const idx = state.quarterFilters.indexOf(quarter);
+      if (idx === -1) {
+        state.quarterFilters.push(quarter);
+      } else {
+        state.quarterFilters.splice(idx, 1);
+      }
+    },
+  },
+});
+
+export const { toggleQuarterFilter } = filtersSlice.actions;
+
+export default filtersSlice.reducer;
diff --git a/site/src/store/store.ts b/site/src/store/store.ts
index d830028da..4dfb04a1d 100644
--- a/site/src/store/store.ts
+++ b/site/src/store/store.ts
@@ -13,6 +13,7 @@ import departmentsReducer from './slices/departmentsSlice';
 import { UserSliceState } from '@peterportal/types';
 import professorSliceReducer from './slices/professorSlice';
 import customCoursesReducer from './slices/customCourseSlice';
+import filtersReducer from './slices/filtersSlice';
 
 const reducer = {
   preview: previewReducer,
@@ -28,6 +29,7 @@ const reducer = {
   departments: departmentsReducer,
   professors: professorSliceReducer,
   customCourses: customCoursesReducer,
+  filters: filtersReducer,
 };
 
 export function generateStore(user: UserSliceState) {