diff --git a/website/src/lib/components/file-list/FileListNodeLabel.svelte b/website/src/lib/components/file-list/FileListNodeLabel.svelte
index cb4516f1..a84115d3 100644
--- a/website/src/lib/components/file-list/FileListNodeLabel.svelte
+++ b/website/src/lib/components/file-list/FileListNodeLabel.svelte
@@ -2,19 +2,28 @@
 	import { Button } from '$lib/components/ui/button';
 	import * as ContextMenu from '$lib/components/ui/context-menu';
 	import Shortcut from '$lib/components/Shortcut.svelte';
-	import { dbUtils, fileObservers } from '$lib/db';
-	import { Copy, MapPin, Trash2, Waypoints } from 'lucide-svelte';
-	import { ListLevel, ListWaypointItem, type ListItem } from './FileList';
+	import { dbUtils, fileObservers, settings } from '$lib/db';
+	import { Copy, MapPin, Plus, Trash2, Waypoints } from 'lucide-svelte';
+	import {
+		ListFileItem,
+		ListLevel,
+		ListTrackItem,
+		ListWaypointItem,
+		type ListItem
+	} from './FileList';
 	import { selectItem, selection } from './Selection';
 	import { _ } from 'svelte-i18n';
 	import { getContext } from 'svelte';
 	import { get } from 'svelte/store';
 	import { gpxLayers } from '$lib/stores';
+	import { Track, TrackSegment } from 'gpx';
 
 	export let item: ListItem;
 	export let label: string | undefined;
 
 	let orientation = getContext<'vertical' | 'horizontal'>('orientation');
+
+	const { verticalFileView } = settings;
 </script>
 
 <!-- svelte-ignore a11y-click-events-have-key-events -->
@@ -77,6 +86,41 @@
 		</Button>
 	</ContextMenu.Trigger>
 	<ContextMenu.Content>
+		{#if $verticalFileView && $selection.size === 1}
+			{#if item instanceof ListFileItem}
+				<ContextMenu.Item
+					on:click={() =>
+						dbUtils.applyToFile(
+							item.getFileId(),
+							(file) => file.replaceTracks(file.trk.length, file.trk.length, [new Track()])[0]
+						)}
+				>
+					<Plus size="16" class="mr-1" />
+					{$_('menu.new_track')}
+				</ContextMenu.Item>
+				<ContextMenu.Separator />
+			{:else if item instanceof ListTrackItem}
+				<ContextMenu.Item
+					on:click={() => {
+						let trackIndex = item.getTrackIndex();
+						dbUtils.applyToFile(
+							item.getFileId(),
+							(file) =>
+								file.replaceTrackSegments(
+									trackIndex,
+									file.trk[trackIndex].trkseg.length,
+									file.trk[trackIndex].trkseg.length,
+									[new TrackSegment()]
+								)[0]
+						);
+					}}
+				>
+					<Plus size="16" class="mr-1" />
+					{$_('menu.new_segment')}
+				</ContextMenu.Item>
+				<ContextMenu.Separator />
+			{/if}
+		{/if}
 		{#if item.level !== ListLevel.WAYPOINTS}
 			<ContextMenu.Item on:click={dbUtils.duplicateSelection}>
 				<Copy size="16" class="mr-1" />
diff --git a/website/src/lib/components/toolbar/tools/routing/RoutingControls.ts b/website/src/lib/components/toolbar/tools/routing/RoutingControls.ts
index b8225be2..4945762a 100644
--- a/website/src/lib/components/toolbar/tools/routing/RoutingControls.ts
+++ b/website/src/lib/components/toolbar/tools/routing/RoutingControls.ts
@@ -9,7 +9,7 @@ import { toast } from "svelte-sonner";
 import { _ } from "svelte-i18n";
 import { dbUtils, type GPXFileWithStatistics } from "$lib/db";
 import { selection } from "$lib/components/file-list/Selection";
-import { ListFileItem, ListTrackSegmentItem } from "$lib/components/file-list/FileList";
+import { ListFileItem, ListTrackItem, ListTrackSegmentItem } from "$lib/components/file-list/FileList";
 import { currentTool, Tool } from "$lib/stores";
 import { resetCursor, setCrosshairCursor, setGrabbingCursor } from "$lib/utils";
 
@@ -391,16 +391,25 @@ export class RoutingControls {
 
         if (!lastAnchor) {
             dbUtils.applyToFile(this.fileId, (file) => {
+                let item = get(selection).getSelected()[0];
+                let trackIndex = file.trk.length > 0 ? file.trk.length - 1 : 0;
+                if (item instanceof ListTrackItem || item instanceof ListTrackSegmentItem) {
+                    trackIndex = item.getTrackIndex();
+                }
+                let segmentIndex = file.trk[trackIndex].trkseg.length > 0 ? file.trk[trackIndex].trkseg.length - 1 : 0;
+                if (item instanceof ListTrackSegmentItem) {
+                    segmentIndex = item.getSegmentIndex();
+                }
                 if (file.trk.length === 0) {
                     let track = new Track();
                     track = track.replaceTrackPoints(0, 0, 0, [newPoint]);
                     return file.replaceTracks(0, 0, [track])[0];
-                } else if (file.trk[0].trkseg.length === 0) {
+                } else if (file.trk[trackIndex].trkseg.length === 0) {
                     let segment = new TrackSegment();
                     segment = segment.replaceTrackPoints(0, 0, [newPoint]);
-                    return file.replaceTrackSegments(0, 0, 0, [segment])[0];
+                    return file.replaceTrackSegments(trackIndex, 0, 0, [segment])[0];
                 } else {
-                    return file.replaceTrackPoints(0, 0, 0, 0, [newPoint]);
+                    return file.replaceTrackPoints(trackIndex, segmentIndex, 0, 0, [newPoint]);
                 }
             });
             return;
diff --git a/website/src/locales/en.json b/website/src/locales/en.json
index d526075b..09781343 100644
--- a/website/src/locales/en.json
+++ b/website/src/locales/en.json
@@ -2,6 +2,8 @@
     "menu": {
         "new": "New",
         "new_filename": "new",
+        "new_track": "New track",
+        "new_segment": "New segment",
         "load_desktop": "Load...",
         "load_drive": "Load from Google Drive...",
         "duplicate": "Duplicate",