Exploring Monhegan Island: 3 Must-Hike Trails for Every Nature Lover
Monhegan Island, perched 10 miles off the coast of Maine, feels like stepping into another world. With a history steeped in maritime lore and artistic inspiration, this tiny island has been captivating visitors for centuries. Originally a fishing settlement, it became a haven for artists drawn to its rugged beauty and dramatic light. Today, Monhegan remains a (mostly) car-free paradise, where life slows down to the rhythm of ocean waves and seabird calls.
With only a handful of year-round residents, the island’s charm lies in its peacefulness. In fact, basically all of the amenities for non-residents shut down after October. By May, however, the island comes alive with art galleries, bustling inns, and a full ferry schedule from New Harbor, Boothbay Harbor, and Port Clyde. The hiking trails are a highlight, providing stunning views, vibrant ecosystems, and a dose of adventure. We are so thankful to the hard work of Monhegan Associates for preserving this beautiful island, and its twelve miles of hiking trails. To embark on your own quintessential Maine reprieve from the hustle and bustle, start planning your 2025 summer or fall hiking weekend now - the limited lodging on the island books up fast!
Directions and Resources for Your Monhegan Adventure
Getting There: Ferries to Monhegan run from Port Clyde year-round, with additional routes from Boothbay Harbor and New Harbor in summer. Plan ahead, as ferry schedules can vary by season. We don’t recommend visiting between November and April unless you have confirmed lodging plans; most accommodations are closed for the off season.
Trail Maps: The Monhegan Associates, a nonprofit organization that preserves much of the island’s natural beauty, provides free maps at the ferry landing. You can also pick one up at the Monhegan Museum.
What to Bring:
Comfortable hiking boots for rocky terrain.
Layers to adapt to Maine’s changing weather.
A reusable water bottle and snacks for energy.
Binoculars for spotting seabirds and seals.
Stay and Eat:
For lodging, check out the Island Inn for a world-class lodging AND dining experience steps off the ferry.
For meals, visit Monhegan Brewing Co. for a casual bite or The Novelty, inside the Monhegan House for pizza and ice cream.
Here are three must-explore trails on Monhegan Island that showcase its unique beauty. And we even included a BONUS at the end you won’t want to miss!
1. WhiteHead Trail
A showcase of Monhegan’s most dramatic cliffs, with sweeping views of the Atlantic that make you feel on the edge of the world.
Overview of the Hike
White Head Trail is a moderately challenging hike that rewards adventurers with jaw-dropping ocean vistas and the sensation of standing atop the world. The path winds through a mix of open meadows and dense coastal forests before opening up to Monhegan’s famous cliffs, which soar 160 feet above the crashing waves. As you approach White Head, the roar of the ocean grows louder, and the salty sea breeze carries hints of adventure. The cliffs’ rugged beauty contrasts sharply with the rolling green of the surrounding hills, creating a landscape that feels wild and untamed.
Insider Tips
For the best experience, tackle Whitehead Trail in the early morning, when the sun rises over the ocean, casting the cliffs in a golden glow. Keep an eye out for nesting seabirds, like black guillemots and cormorants, who thrive on these cliffs. Along the way, you’ll spot coastal wildflowers such as beach rose and seaside goldenrod, adding splashes of color to the trail. Be cautious near the cliff edges—while the views are breathtaking, the drop-offs are steep and unforgiving.
Location: Monhegan
Distance: 1.9 miles (Loop)
Difficulty: Moderate
Trailkeeper: Monhegan Associates
2. Lobster Cove
This coastal trail leads to a historic shipwreck and tide pools teeming with marine life, making it a favorite for history buffs and nature enthusiasts alike.
Overview of the Hike
Lobster Cove Trail is a leisurely hike with rich rewards. The trail meanders along Monhegan’s rocky shoreline, offering views of lobster boats bobbing in the water and gulls soaring overhead. The centerpiece of the trail is the wreck of the DT Sheridan, a tugboat that ran aground during a storm in 1948. Its rusting remains lie scattered along the rocky beach, lending an eerie beauty to the landscape. Beyond the shipwreck, tide pools brim with crabs, sea anemones, and tiny fish darting among the seaweed. It’s the perfect spot for a picnic, where you can sit on sun-warmed rocks and take in the ocean’s rhythmic ebb and flow.
Insider Tips
Low tide is the best time to explore Lobster Cove Trail, as it reveals the most tide pools and allows you to get up close to the shipwreck. Wear sturdy shoes with good grip—wet rocks can be slippery. Keep an eye out for seals lounging on nearby rocks and listen for their occasional barks over the waves. If you’re visiting in the fall, this trail offers some of the island’s best spots for spotting migrating monarch butterflies.
Make it a loop by following Lobster Cove Trail until you hit Lobster Point and hang a left to follow along the Cliff Trail for 0.6 miles until you hit the Underhill Trail. Take a left there and follow it 0.3 miles until you hit Lobster Cove Rd., which leads right to the original trailhead!
Location: Monhegan
Distance: 1.1 miles (Loop)
Difficulty: Moderate
Trailkeeper: Monhegan Associates
Note: The AllTrails route above does not reflect the loop route but is instead the first leg of the short loop.
3. Cathedral Woods
This enchanting forest trail feels like stepping into a fairy tale, complete with towering spruce trees and whimsical fairy houses tucked among the roots.
Overview of the Hike
Cathedral Woods Trail is a gentle, magical hike that transports you into Monhegan’s serene interior. The forest canopy towers overhead, with sunlight filtering through the needles and illuminating the soft moss-covered ground. Along the trail, you’ll notice miniature fairy houses crafted from sticks, leaves, and stones—a long-standing tradition on the island that delights children and adults alike. The air is filled with the earthy scent of spruce and the occasional trill of songbirds. The quiet here is profound, broken only by the rustle of leaves or the distant crash of ocean waves.
Insider Tips
To fully appreciate Cathedral Woods, slow down and immerse yourself in the details. Look closely at the undergrowth, and you might spot native mushrooms like the striking red-capped fly agaric. Bring a notebook or camera to capture the intricate designs of the fairy houses—some are true works of art. This trail is particularly magical after a light rain, when the moss glows an almost neon green, and the forest feels alive with energy.
Location: Monhegan
Distance: 1.0 miles (Loop)
Difficulty: Moderate
Trailkeeper: Monhegan Associates
Bonus: Cliff Trail Loop
If you’re feeling extra adventurous, consider getting a taste of all of the above and more by circumnavigating the island - or perhaps taking the Whitehead trail (mentioned in #1 above) until it joins up with the Cliff Trail around the northern tip of the island, which will lead you back to town after tacking on a couple of view-packed miles. Regardless, the 4.4 miles are worth it, but not for the faint of heart. We’d consider this one “hard” despite the relatively small elevation gain of 538 ft.
Why Monhegan’s Trails Are Worth the Journey
Monhegan Island may be small, but its hiking trails pack a punch. From dramatic cliffs and enchanting forests to historic shipwrecks and biodiverse tide pools, the island offers something for everyone. Whether you visit during the bustling summer or the tranquil winter, these trails promise unforgettable experiences. So lace up your hiking boots, catch a ferry, and prepare to fall in love with Monhegan’s wild beauty—one trail at a time.
