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3 Day Travel Itinerary: Monhegan Island, Maine


The Wharf, Monhegan Island, Maine
The Wharf, Monhegan Island, Maine

This 3 day Working Joe Travel Itinerary explores the slightly scruffy and picture perfect Monhegan Island. Situated ten miles off the coast of Maine, the Island is widely referred to as an artist’s colony – but don’t go expecting a highbrow New England village. Monhegan Island is rocky, wind-blown, and exquisitely common.

There is not a lot of fancy at this vacation destination, just accessible breathtaking landscapes. The roughly one-square-mile island surprises with raw beauty around every corner, whether it is viewed under a blue sky or shrouded in fog. We have visited several times, and yet the small island maintains an air of feral mystery.

Ferries depart for Monhegan Island from three different ports. This trip planner recommends the Hardy Boat Cruise line located in the tiny fishing village of New Harbor, Maine. Parking is free with the purchase of a ticket (the grassy lot is a short walk from the wharf). We like that, after parking, we spend the weekend on foot as there are no vehicles allowed on the island – except for the locals.

Lobster Boats of Monhegan Island, Maine
Lobster Boats of Monhegan Island, Maine
Travel Itinerary At-A-Glance Monhegan Island

For more information on traveling to Maine read our articles on:


3 Day Working Joe Travel Itinerary

Day 1: Leave home early enough so you can enjoy the afternoon. Most routes will lead you to Bath, Maine. Stop in the city for a bottle of champagne or your favorite liquor. Monhegan Island is “dry,” but you can bring-your-own alcohol. From Bath, the secondary roads to New Harbor are scenic and well signed.


In quiet New Harbor, we like to stay at the Gosnold Arms Inn. We find the rooms a bit pricey, but they are clean and the location cannot be beat. The inn is right across the street from the harbor and ferry departure point. Check-in and drop your bags. Then, go park the park the car and purchase tickets for the ferry.

Buoys on Monhegan Island
Buoys on Monhegan Island

This evening cross the street once more to Shaw’s Wharf. Have a beer at the raw bar and watch the lobster boats unload their catch. When ready, migrate upstairs to the restaurant and order fresh seafood served on paper plates. Find a picnic table on the outside deck and study the boats bobbing in the harbor. Before turning in, stroll to the end of the pier across the street from the inn. Enjoy the solitude and the stars until the bugs chase you back inside.

Day 2: Dress for a hike and have breakfast in the lovely Gosnold Arms Inn dining room while gazing out over New Harbor. Checkout and roll your bag across the street to the cruise line. There is always something fun to see on the ferry ride; seals on the rocks or an artist sketching on-board. Once we saw a dead whale floating in the swell (disgusting, but riveting). Dock mid-morning on Monhegan Island and check-in to your lodging.

Monhegan Island Coastline
Monhegan Island Coastline

For such a small place there are many different types of accommodations. Overall, the flavor of the island is rustic elegance. Our favorite place to stay is the Island Inn. The restaurant is charming and the view from the porch overlooking the harbor is quintessential Maine. Plus, the Inn is the shortest distance between the ferry and most other lodgings. Since the roads are dirt and the trucks the locals drive fly(!), you will appreciate this tip.


After unpacking, make a dinner reservation (sit down restaurants on the island are few). Then grab your trail map and head out for a hike. There is hiking on Monhegan Island for many different abilities. Some are challenging. Not all are well marked. Depending on your route, you might pass a shipwreck, soaring cliffs, or crashing surf.

Tides of Monhegan Island, Maine
Tides of Monhegan Island, Maine

Once out on the trail, the forest is thick and the crowds few. Away from the bustle of the wharf the isolation is magnificent. The scenery is wild and majestic, both wooded and coastal. Along the ragged and sometimes unkempt trails you will likely sweat, swear, and take some of the most unbelievably beautiful photos in your collection.

Back at your room take a nap and a long hot shower. If you are staying at the Island Inn claim two rocking chairs on the porch and enjoy a bottle of wine while the sun goes down. Then relax over a long, late dinner in the Inn’s dining room before turning in (there is really no nightlife on the island so you must make your own fun).

The Horizon | Monhegan Island, Maine
The Horizon | Monhegan Island, Maine

Day 3: After breakfast, pack up. Store your bags, and then head out to explore the island’s shops and artist’s studios. Wandering around the village’s dirt lanes there is character in every weathered shingle and wind-blown crag. We usually depart in the mid-afternoon. If you are lucky, as the ferry departs you will be treated to a jumping display by the local teens as they leap from the wharf into the harbor.

Travel Tips:

Children: Best for children who are sturdy, mobile, and love the outdoors. There are few planned activities and little indoor entertainment.

Electronics: Few TVs/electronics. Little access to the web.

Food: Can be hard to come by and expensive. Bring-your-own-liquor and snacks.

Hiking: Panoramic vistas. Study the trail map before setting out. It is easy to get lost (but not for long as the island is so small). At a minimum bring hiking boots, bug spray, a whistle, and a jacket with a hood (the weather changes quickly).

Swimming: One beach (tiny, exposed, and scruffy).

Transportation: Your feet and be QUICK to get out of the way of the local drivers.

Cairn on Monhegan Island
Cairn on Monhegan Island

Safe travels, Laura and Randy

For more information on traveling to Maine read our articles on:





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