Islands in the Bay

Casco Bay is home to seven lighthouses, eight forts, and 785 islands (including exposed ledges). From Portland, Casco Bay Lines ferries service six of the offshore islands, five of which are inhabited year-round. Each of them has its own flavor and personality; we talked to residents for the inside story on these unique places to live.

Cliff Island

It takes nearly two hours by ferry to reach Cliff Island, the last stop on the Casco Bay Lines run. It is a place where children’s playing voices ring out across the fields, bikes are scattered along unpaved roads, driftwood takes the place of car bumpers, and everyone says hello. “I feel like for each person out here and for every kid out here it’s their island. It’s their place,” says Hope MacVane-Tray, a lifelong resident and owner of the Cliff Island Store and Cafe, the island’s only shop. A chalkboard outside advertises “Homemade Blueberry Muffins, Watermelon, and Lobster Rolls” while another asks for leftover egg cartons. “Growing up on the island was quiet and very isolating,” MacVane-Tray explains as she tightens her light green paisley apron. “As a teenager I think I didn’t enjoy it as much, but now I look back and I notice it’s pretty amazing—the island is a part of who I am and for that I feel very fortunate.” The feeling of being a part of something special is a common thread. “There’s such a way of working together and it’s just magical,” adds Elizabeth Berle, MacVane-Tray’s childhood friend. “It’s something you would only get in a setting like this.” Two miles long by one mile wide, Cliff Island is home to about 200 residents during the summer months and 40 during the winter. It has a oneroom schoolhouse, chapel, library, post office, and on-island conservation team. The majority of year-round residents rely on lobstering for their living. “There’s my father’s lobster boat, the Lady J,” MacVane-Tray says as we walk along her family’s wharf on Griffin’s Cove. Behind her, children and adults race along the pier and cannonball into the water, a summertime activity for generations, she says. As we head back toward the village, a bright yellow soccer ball shoots out of the trees and rolls across our path. Soon to follow is a group of sunburned boys in the middle of an afternoon match. “You see how none of them are wearing shoes?” Berle says. “It’s called island feet. My son takes his shoes off at the beginning of the summer and doesn’t put them on again until school starts. It’s like a badge of honor, getting to grow up with island feet.” -Blair Best.

Peaks Island

Just three miles from the Casco Bay Lines ferry terminal in Portland, Peaks is the most populated of the Casco Bay islands, with close to 1,000 year-round residents. Amenities include a branch of the Portland Public Library, a good-sized market, two hotels, and a few casual restaurants. In the summer, daytrippers stream through the iconic green gate of the ferry landing to spend a few hours wandering shaded island paths, visiting the backshore beaches, or exploring the remains of World War II–era forts. Even in mid- July, however, Peaks is considerably quieter than it was in the late nineteenth century, when the island had several hotels, theaters, and an amusement park, and was known as the Coney Island of Maine.

“On a beautiful summer day I love sitting on the lawn of my grandparents’ house—the house I grew up in—looking across the bay to Portland while family comes and goes,” says Amanda O’Brien, who moved to Peaks when she was two. “It’s part nostalgia, part postcard.” Following in the footsteps of her mother, an island native who left as a teenager and later returned to raise her daughter, O’Brien went to college in New Hampshire and lived in other parts of the country before becoming a mother herself. “When I had my son I realized Peaks was an amazing place to raise a child,” she says. She bought an old house one street over from her parents when Emmett O’Brien, now five, was 11 months old. “Being a single mom, it’s been a great place for me and my son. Someone will bring my trashcan in, or plow my driveway, and I’m not always sure who did it.”

O’Brien, the director of business development at Flyte New Media and co-founder of Eighteen Twenty Wines, both in Portland, thinks of Peaks as a Portland suburb, albeit one surrounded by water. “There’s a whole group of us who take the 7:15 or 8:15 boat to make it to our jobs,” she says. “I have coworkers who think my commute’s crazy, but I can get from Peaks to Commercial Street in 20 minutes.” Living on the island has even helped her appreciate Maine winters, when islanders pitch in to help each other, and her commute is less crowded. “It’s easier to compartmentalize life when at the end of the day you have to make the 5:30 boat,” she says. “Work is here; then I take a boat ride and my family is over there,” she says. “It’s been very good for my mental health.” -Susan Axelrod.

Great Diamond Island

Rick Frantz recalls how he felt when he and his wife, Jennifer Fox, moved to Great Diamond Island. “It was October and the leaves on the trees were all different colors,” he says. “I remember this incredible feeling when it got dark and I watched the ferry just sort of disappear. That’s when it first hit me. It was like watching our last link float away and I remember thinking, ‘Wow.’”

Frantz, the co-owner of Andy’s Old Port Pub, and Fox moved from New Hampshire to Great Diamond about 18 years ago. “When I first moved to the island, the longest I stayed for one period of time was three weeks,” Frantz says. “When I came off the island it was spooky. I didn’t know that it could only take three weeks for everything on the mainland to feel so different.” The couple describes moving to Great Diamond as a magical accident. “We hadn’t ever really thought about living on an island before,” Frantz laughs. “I remember Jennifer telling me that we had to meet our realtor on a water taxi. I didn’t even know what a water taxi was.”

In the late nineteenth century, after the Spanish-American War, about half of the island operated as Fort McKinley, the largest of five forts built to defend Portland Harbor. After World War II, the military base sat abandoned until the 1980s, when developers renovated the brick buildings into a private community with amenities such as tennis courts and a bowling alley. This side of the island is known as Diamond Cove. The other half of the island was established as a summer colony called Diamond Island Association in the 1880s. “There’s only a core group of us that are on the island year-round—about 64 of us—and we know and respect each other’s side,” Frantz says.

The islanders on Great Diamond experience a camaraderie that Fox describes as “the kind of thing you don’t even understand until you’re involved.” This sense of community is common to the Casco Bay islands, and it happens by way of the ferry service. “The longer we are out there the more we realize that the ferry is like a whole other island in itself,” Frantz explains. “There is a personality in the ferry and you sort of have a family on there. It’s like you’re all part of the same tribe.” -Blair Best.

Chebeague Island 

Ten miles from Portland, Chebeague Island is the largest offshore (i.e. not connected to the mainland by a bridge) island in Casco Bay, and one of two that is its own town. Until 2007, when its residents voted to secede, Chebeague was part of Cumberland. (Long seceded from Portland in 1993, while Cliff, Great and Little Diamond, and Peaks all belong to Portland.) Three miles long by a mile wide, Chebeague has a library, recreation center with an outdoor pool, fire and rescue services, even an assisted living facility, Island Commons.

While summer visitors swell the population considerably, Chebeague has a year-round population of about 400, a number that may be slowly increasing as people discover it can be an idyllic place to raise a family. “It’s ahidden gem,” says Kevin Wentworth, who moved to the island 15 years ago. He and his wife, Polly, a fifth-generation “summer person” from Philadelphia, are raising their nineyear-old twins, Alden and Olivia, in Polly’s grandparents’ former home. “I’m so excited for my kids because they are getting to grow up in the best place,” says Kevin Wentworth. “In July, you can go down to the sandbar that connects to Little Chebeague Island at low tide and you can be the only one on that beach.”

Now in his second season as the owner of Chebeague Water Taxi, Wentworth, a former ferry captain, is an enthusiastic ambassador for the island, as well as the provider of an important service. From pre-K through fifth grade, children attend the Chebeague Island School (Wentworth is also the schoolbus driver), but for middle and high school, they go to Yarmouth. “So many families were missing the last boat for things like their kid had a concert and was playing a trumpet solo,” he says. Still, he insists that second only to Peaks Island, Chebeague has “the best combination of ferry services,” allowing residents to commute easily to the mainland.

Wentworth often shuttles guests to the Chebeague Island Inn, a gracious reminder of another era and a center for summertime social life. “Chebeague is the place to just shutdown,” he says. “People ask me, ‘What is there to do?’ and I say, ‘Well, do you like great food, good drinks, relaxing conversation?’”

The Wentworths support local businesses such as Doughty’s Island Market, but like many islanders, they also rely on mail order. “If I’m parked at the town office I’ll go out to my car and my packages will be in the passenger’s seat,” Wentworth says. “It shows the personal side, how people make it work on an island.” -Susan Axelrod

Long Island

On Long Island, John Pearsall’s neighbors don’t know his name. “They just call me the Plane Guy,” he says. Pearsall is the president and CEO of Elite Airways, and about 11 years ago he fell in love with Long Island. After staying for one week in the summer of 2006, Pearsall decided to move his airline from Las Vegas to Portland and build a house on the island. “It’s just a great place to live,” Pearsall says in his office on Portland Pier. “You can come from here in the city, get on that ferry, and be in a totally different world once you reach that island.”

The commute to Long Island is about 40 minutes by Casco Bay Lines ferry. It is a ride that Pearsall describes as a “pretty sweet way of life.” He quickly pulls up a picture on his phone taken on a recent morning. The sky is a dark purple and the island is outlined in gold. “That’s what I see going to work every day on the 6:45 ferry,” he says.

Long Island has two sandy beaches, an elementary school, fresh water pond, library, and conservation hiking trails. It is also recognized as a vital part of the history of Casco Bay. During World War II, the island was used as a Navy base and was one of the largest refueling depots for military vessels in the North Atlantic. It was also the only island to have a seaplane base, which now serves as a boatyard. Pearsall is a familiar face at the island boat yard, which is where he parks his own Lake Renegade. “I fly it everywhere,” says Pearsall. “I’ll take it to meetings or out to the lakes. I also like to fly it over Long Island. The views from up there are just incredible.”

Measuring 1.42 square miles, Long Island is a year-round home for 240 residents. Most of the families are third- or fourth-generation islanders whom Pearsall refers to as “‘the good crowd.’ The people out there are really down to earth. I think that’s what makes Long Island special,” he says. A large number work on the island, many as lobstermen, teachers, or small business owners. Pearsall is part of a small group that commutes daily. “When that ferry comes around, it’s like the school bus for everybody. That’s part of what makes it a different way of life out there,” Pearsall says. When asked to describe the island in one word, he chooses “peace.” -Blair Best.



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