Maine’s Magical Islands

From a getaway on Portland’s doorstep to a rugged outpost of Acadia National Park, we explore the special hold that Maine islands have on the imagination.

By Yankee Magazine

Jun 19 2019

A resting place for Monhegan’s visitors for more than a century, the Island Inn is situated on a bluff that provides a commanding view of the harbor and a front-row seat for sunsets.

Photo Credit : Mark Fleming

When we board an island-bound ferry on the coast of Maine, we sense that a different way of life awaits—one where vigilance toward weather and tides and even ferry schedules cannot be taken lightly. Miles out to sea, nature, not man, is in charge.

Where once there were dozens of year-round island communities off Maine’s coast, only 15 remain. But the beauty of the sea, pine-lined paths, meadows, and sweet cottages on bluffs has never ceased inspiring us. Come summer, like clockwork, day-trippers descend with backpacks and vacationers with suitcases.

Here, summer cottages of the famous and wealthy that have been in the family for generations lie tucked behind lush garden hedges and winding dirt driveways. These islands are where they find normalcy, where fishermen and boatbuilders and carpenters have known them and their children simply as neighbors, even if for only a few months a year.

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This was the landscape, both physical and social, that photographers Winky Lewis and Mark Fleming explored last summer on visits to five Maine islands, each one proud of its individual identity, its particular hold on the imagination.

Fishing boats on their moorings in Carver’s Harbor, on the south side of Vinalhaven—an island that is itself surrounded by other, smaller islands, including Lane’s Island (left), a nature preserve.
*Photo Credit : Mark Fleming*

On a fine summer day, when the ferry docks at Peaks Island—only 20 minutes from the bustle of downtown Portland—hundreds of people spill out. You can bike its perimeter in 40 minutes, and that includes pausing to sun yourself on boulders and to buy a jar of honey on the honor system from a tiny roadside stand.

A dozen miles out in Muscongus Bay lies Monhegan, which for more than a century has been an inspiration for artists ranging from Rockwell Kent to Jamie Wyeth. Cliffs tower over the sea, and paths lead to meadows where hundreds of varieties of wildflowers grow.

The two Fox Islands—North Haven and Vinalhaven—are separated by only a narrow thoroughfare, yet they have distinct personalities that reflect divergent histories. North Haven has long been home to the bluest of New England’s blue bloods, as well as artists and writers, while Vinalhaven once teemed with quarry workers, who carved out massive chunks of rock used in the grandest buildings in the land. Today, Vinalhaven’s lobstering fleet is one of the largest on the Atlantic seaboard.

The wildest and most rugged part of Acadia National Park can be found on Isle au Haut, which rewards intrepid hikers with miles of trails and countless indelible views.

Maine Islands Map — Exploring Maine’s Magical Islands
*Photo Credit : Art by Jessica McGuirl*

Below, you’ll discover portraits of these five islands, each described by a longtime resident. The islanders’ words reflect a deep-seated pride and love for their unique slice of Maine—and the moments that Winky and Mark framed with their cameras show why. —Mel Allen

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An Islander’s Peaks Island

Kim MacIsaac | Co-owner, Peaks Island Tours

I’m a fourth-generation islander on my mother’s side, third on my dad’s. But I’m a newcomer. There are people whose family has been here since 1632, even. Almost all the cottages and homes out here are at least 100 years old.

While the other islands in Casco Bay, the inhabited ones, are pretty much fishing islands, with very few people living there, we’re basically a residential island. The year-round people all work; the summer people are here for a good deal of the season, and they’re just part of the community. We do get as many as 2,000 visitors a day in the summer—day-trippers—but we’re really like any other neighborhood in Portland. It’s just that we’re separated from it by three miles of water. We’re more like a little village.

It’s great to come, take a tour, rent a golf cart, rent a bike, go exploring, have a nice meal, a drink at the pub, an ice cream cone. It’s basically just R&R here. Take a vacation from stress.

The logoed cask outside the Inn on Peaks Island is a nod to owner Fred Forsley, the founder of Shipyard Brewing Co.
*Photo Credit : Winky Lewis*

Walking is the preferred method of getting around. Almost everything is accessible from the ferry. A few museums are maybe five or 10 minutes away, but everything else is right there.

That said, the back shore is the spot to go for walks. The best beaches are on the ferry side, but the best views are on the back side of the island. It’s rocky coast, and it’s quieter. There are also hiking paths through the woods—we have almost 200 acres of conservation land.

Be sure to see Battery Steele, a World War II gun bunker. It’s the only one of its size in Maine, and it mounted two battleship guns—huge guns. The island had the largest military base in Casco Bay and somewhere close to 900 soldiers during the war. We’ve got three museums, too, including the Umbrella Cover Museum, which is a hoot. The others are both Civil War museums, theFifth Maine Regiment Museum and the Eighth Maine Regiment Lodge and Museum.

For eating out, I kind of switch back and forth between the Cockeyed Gull and the Inn on Peaks Island. But I also eat at the food truck, Milly’s Skillet, which has a good lobster roll. And really, I try to patronize all the places.

Located on the rocky eastern side, or “back shore,” of Peaks Island, Spar Cove offers views of neighboring Casco Bay islands and, looking directly east, the wide-open Atlantic.
*Photo Credit : Winky Lewis*

The highlight of the summer season out here is the Lions Club variety show in August. You have some professional entertainers in it, you have normal people who have some talent, and then you have the people who have no talent—that’s the best part! We also have an around-the-island road race in July with over 500 racers, all ages, who get together for a cookout afterward.

In addition, we have a community website (peasksisland.info), which gives you all kinds of information about the island. And no, we are not an amusement park anymore! That’s what Peaks Island was known for until about 1930 or so—we had a boardwalk, and a roller coaster down the street, and all kinds of fast-food stands and shops and everything. We tell people if you want amusements, go down Route 1 to Old Orchard Beach. If you want to shop, go over to the mall! —As told to Cathryn McCann

Peaks Island Trip Planner

Food & Drink

The Cockeyed Gull: Eclectic, globally influenced menu in a casual setting, plus a full bar and a deck with Portland skyline views.
Milly’s Skillet: Everything from cinnamon buns and breakfast subs to sirloin burgers and fish tacos, all cooked up in a cheery food truck.

Lodging

The Inn on Peaks Island: Six suites with a seaside-cottage vibe, just steps from the ferry, plus a restaurant serving upscale pub fare and ale brewed on-site.
Eighth Maine Regiment Museum and Lodge: Rustic 1891 building with 14 tidy guest rooms (shared bathrooms).

Getting There

Casco Bay Lines: Daily service from Portland; cars allowed.

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An Islander’sMonhegan

Matt Weber | Lobsterman and co-owner of the Monhegan Brewing Company

The thing with Monhegan is, when you’re out here, you’re out here. You have to disconnect. It’s not like going to Cadillac Mountain or Sand Beach in Bar Harbor, where you can be back at your car in five minutes. Here you’re at least an hour by boat from anything.

It’s a little more rugged. Think sneakers, not flip-flops. Bring a sweatshirt. Pack it in, pack it out. There are public restrooms, but if you’re on the back side of the island, you’re going to have to walk a little ways to get to them.

A resting place for Monhegan’s visitors for more than a century, the Island Inn is situated on a bluff that provides a commanding view of the harbor and a front-row seat for sunsets.
*Photo Credit : Mark Fleming*

No bike trails, but lots of places to walk. Cathedral Woods is a big forest—dark and quiet and cool—and feels like you’re in a storybook. About 15 minutes from the road, you’ll start to see all these little branches and pine needles and pine cones that people have put together to make fairy houses. I take my niece and nephew out there every year, and they play around in there for hours.

On the very south end of the island, at Lobster Cove, there’s an old tugboat that went ashore in the late ’40s. The hull is still mostly intact, and you can sit right on it and look out to sea. There’s almost always a nice sea breeze, and it’s not uncommon to see whales or porpoises or seals from that spot. All of a sudden, you think, Where in the heck is this place?

The Monhegan Museum is also pretty amazing—artwork by Edward Hopper, all three generations of Wyeths, to name a few— but it’s a museum of art and history, so it’s all about the island, too. You can get a tour to the top of the lighthouse, and the view from up there is the Gulf of Maine on one side, the coast on the other, and all the islands in between. It’s a really cool thing.

Reborn in 1968 as the Monhegan Museum, this 19th-century lighthouse station holds some of the island’s most prized art and artifacts.
*Photo Credit : Mark Fleming*

At 2 o’clock you can go down to the dock and hop on the ferry from Boothbay Harbor, the Balmy Days II, which does a little guided trip around the island and out to the Duck Rocks and back. I’m not sure a lot of people know about it. It’s a great way to see the back of the island from the water, which I get to do all the time when I’m lobstering. When I was first out here, the trip cost a dollar, and now it’s like four or five. Can’t beat it for that.

Even in summer the water seems pretty cold to me, but you know how it is when you’re a kid—it doesn’t seem to matter. The bigger kids jump off the dock, the smaller kids are at Swim Beach, and now everyone’s got kayaks and paddleboards, so there’s always a little fleet roaring around the harbor.

Shermie, one of our older fishermen, he’s been here for five generations now. He runs the Fish House, and you go in and you order food and it gets cooked up right there. The seating is outside, basically on the beach, and you’re right at the harbor, and it’s perfect.

Fifth-generation lobsterman Shermie Stanley, who also serves as Monhegan’s harbormaster and runs a popular seafood shack.
*Photo Credit : Mark Fleming*

Signs and fliers crowd onto the wall of the Rope Shed, aka Monhegan’s community bulletin board.
*Photo Credit : Mark Fleming*

Our brewery does bring over a band from the mainland for our July Fourth birthday party, when we have live music and stay open a bit later, and we have a couple of special “secret” beers that we pour that night. At the same time there’s a group of musicians on the island—fiddles, violins, a big bass—and about once a week they’ll have an impromptu jam session right on the front deck at the brewery, and that’s pretty fun too. We never know when—they just show up, have a few beers, and start playing.

The thing that we all talk about here more than anything else—and our favorite thing to talk about—is Monhegan. What has happened to me and most of the people who live here, I think, is you may never have really planned on spending your life here, and then you realize you couldn’t live anywhere else. Monhegan just sneaks up on you and shows you something about life that you might never have seen or understood before. —As told to Jenn Johnson