HikerMonhegan Island Hiking: Trails, Map & Your Island Challenge
Explore Monhegan’s named paths, choose a manageable outing and build an island hiking collection across as many visits as you like.
Independent HikerQuests guide · Sources reviewed October 13, 2026
An island worth returning to
There is more than one way to enjoy a hiking island. You might spend a first visit on one coastal destination, return for woodland paths, then slowly connect the remaining sections. This collection gives those smaller walks a place alongside the big views. It is built around named trails, original planning notes and your own records—not a requirement to hurry around the island in one day.
A clearly defined personal challenge
Our checklist has 17 entries: 15 numbered trail names, the Lobster Cove approach, and one grouped entry for the separate 1A connectors. Numbers 2, 8 and 13 are not supplied as invented missing trails. Follow the latest official map and any closures; this versioned list is a personal HikerQuests project, not a land-trust award or a claim to catalogue every informal path.
Plan beyond the trail
Use MonheganMaine.com to explore the wider island visit. HikerQuests concentrates on your walking plan and personal trail collection, while the sister guide provides a place to continue discovering Monhegan. The shop is an optional browsing stop after planning, not a requirement for challenge participation.
Monhegan trail map & checklist
Explore the trails, then sign in to save your own progress.
Blue: not recorded · green: recorded · dashed: separate 1A connectors. A saved visit counts in your challenge; use a full-trail completion date for this personal checklist. This is not a live location map.
Use the complete trail list below if the map is unavailable.
Planning reference: © OpenStreetMap contributors, ODbL. Extracted October 14, 2026 UTC. Download source GeoJSON · Map limitations & instructions. Lines may be incomplete; carry the current official paper map and follow local signs.
Cliff Trail
Follow the island’s headlands in sections
Sign in to track this trail →Underhill Trail
A southern connection worth remembering
Sign in to track this trail →Burnt Head Trail
Make room for a headland pause
Sign in to track this trail →Gull Cove Trail
A cove destination with its own approach
Sign in to track this trail →Alder Trail
Give the connecting paths their moment
Sign in to track this trail →Whitehead Trail
From village-side approach to ocean outlook
Sign in to track this trail →Red Ribbon Trail
An interior path for a slower island day
Sign in to track this trail →Black Head Trail
Plan the approach as carefully as the destination
Sign in to track this trail →Cathedral Woods Trail
Let the woodland be the main event
Sign in to track this trail →Long Swamp Trail
A named woodland section, not a shortcut to improvise
Sign in to track this trail →Pebble Beach Trail
Follow the current path toward the northern coast
Sign in to track this trail →Evergreen Trail
Build a woodland chapter into your challenge
Sign in to track this trail →Maple Trail
Small connections complete the bigger story
Sign in to track this trail →Fern Glen Trail
Choose a northern woodland connection deliberately
Sign in to track this trail →Station Hill Trail
The last number is not the trail count
Sign in to track this trail →Lobster Cove approach
A village-to-cove outing beyond the numbered trails
Sign in to track this trail →1A connecting paths
Several separate connectors share one label
Sign in to track this trail →Make progress across several visits. Never enter a closed section to finish a checklist. Our 17-entry collection groups 15 numbered trails, the Lobster Cove approach and the separate 1A paths; it is not an official award or a claim that every informal island path is mapped.
