We had been warned.

It should have been little surprise to us when the older woman — she never told us her name — appeared from around a corner of low bushes. She piloted the golf cart expertly, coming to a stop just a few feet ahead of us.

“Can I help you gentlemen?” she asked, almost genuinely.

“I think we’re all set,” answered my companion.

“We’re just heading back to the dock,” I added.

“Well, you’re not heading back that way,” she assured us. “You can’t have come from that way. Why don’t you get in and I’ll take you back?”


Her little dog yapped from the passenger seat.

“No, that’s okay. We can find it.”

“Why don’t you just hop in and I’ll take you back down there?” It was a question, but you never would have guessed that.

In the end, we conceded. As we jostled over winding roads, making our way back to the other dock, my friend looked at me.

“I guess they were right,” he said, smiling.

Let me back up.


Every summer I have the immense pleasure of spending a day on a Casco Bay island on behalf of the Sun Journal. I’ve seen the crowded attractions, both natural and commercial, on Peaks Island. I beached and biked on Long Island. And I was nearly stranded for a night on Chebeague. (If it hadn’t been for the kind owners of the inn there, who managed to get me back to Portland, I would have been bunking down in an open field.)

This summer, I decided to visit Great Diamond Island, a relatively popular day-trip destination among mainlanders for its serene vistas and its proximity to Portland. A 30-minute ferry ride from downtown, Great Diamond is actually a part of the city of Portland. With a year-round population just shy of 100 residents, the island is a quiet, sleepy and very natural spot. It is made all the more natural by its limited network of streets and its lack of cars (there are some, but because they can’t be brought over by ferry, almost everyone rides golf carts or bicycles).

The island was once an artistic retreat, visited by Henry Wadsworth Longfellow and Harriet Beecher Stowe, among others. Leading up to the Spanish American War, an enormous military installation was developed on Great Diamond with the aim of protecting Casco Bay from the dreaded Spanish navy. Much of the island was converted to this purpose and Fort McKinley, as it was called, sprawled across Great Diamond.

Construction ended in 1907 and the installation was in use until the end of World War II in 1945. However, the military subsequently vacated the space, which sat empty for more than 30 years until it was developed into a large private community called Diamond Cove. Though there are no gates, visitors to the island are generally not allowed to enter this property without permission. 

And therein lies the interesting, dual nature of Great Diamond Island. The western part of the island is much like Peaks: Private homes and rentals, seasonal and year-round residents, a community center that welcomes visitors, beaches and walking trails open to all. The eastern portion, on the other hand, contains a public restaurant and a public general store, while all else is off limits except to residents of Diamond Cove and their guests. The island even has two separate ferry stops, one called “Great Diamond” and the other, “Diamond Cove.” There is one public road that connects the two sides of the island.

This history, and the division of the island, was quickly explained to me when I arrived on the island with my travel companion, another reporter named Matt. We had even heard from a friend who works on the island that we should be cautious when visiting, as much of the island is off limits to visitors.


We exchanged curious looks as we stepped off the ferry and onto the Great Diamond dock. We had decided in advance that we would look for a nearby public beach.

“I wonder if it’s safe to walk here,” I said, jokingly.

There was a paved road leading away from the dock that meandered up a hill and out of sight. Beside us, on the right, was a thin strip of beach that ran in a crescent shape around a long cove in which small boats were anchored.

We began walking up the road, our only visible option. Two-hundred yards along, we sighted a group of four traveling in the other direction. As we approached, Matt and I glanced at each other, silently conveying our concern that we were about to be scolded or shooed along.

The group eyed us as we converged. Preemptively, I introduced myself as a reporter and asked if there was a public beach somewhere close by. And as one of the group began to respond, we realized just how unnecessary our concern had been.

“There’s a nice beach in front of Elwell Hall, which is the community hall on this side of the island,” said one of the group, who introduced herself as Barbara Raimondi.


As we became more comfortable, I asked Barbara if there were things that a day-tripper to the island should make sure to see. Barbara gave us a list of things to do (check out the sidebar at right for those and other suggestions) and then asked if we had been to the community center.

No, we told her, we had just gotten off the ferry.

“You want to see it?” she asked. “Okay, I’ll walk you over.”

Barbara, who spends much of her summer on the island but keeps a permanent residence in Auburn, told us more about her side of the island as we walked. “It’s got public roads. The other side, the ‘Cove’ side, is private and it’s posted.”

She told us about the community center and about the small lending library.

“We have community suppers,” she told us, “almost every weekend. We have a summer fair.” Both of which, she explained, welcome people from off the island.


Matt and I realized that we couldn’t have run into a more welcoming or more helpful tour guide. We made our way to the community center. As we passed people along the way, Barbara exchanged familiar greetings. It was clear that she was a well-known personality within the small summer community on the island.

She offered to give us a tour of the community center, starting with the store in the basement. As we walked through, I pointed out a sign on a refrigerator. Handmade, it advertised free Popsicles, one per day.

“Oh yes,” she chuckled, “well, the store’s not really meant to make a profit. It’s all volunteers. It’s for the community. They try to break even.”

From our tour — not to mention our tour guide — we were beginning to develop a clearer sense of Great Diamond Island, at least this part of it: Warm, welcoming and open.

We went upstairs, where a crew of volunteers was preparing for that evening’s lobster dinner. Barbara introduced us to Anne Wheeler, a fourth-generation islander.

Anne filled us in on the history of the island. She also told us about some of the more recent changes that have taken place.


“There’s a lot of new cottages being built,” she said, a trend that began in the ’80s when a tax reassessment forced owners to sell off expensive waterfront parcels and move inland.

“Definitely more people,” Anne said. “There’s a lot more year-rounds, but it’s a mix.” As a child, she said, there were only three families living on the island throughout the year.

As we walked out of Elwell Hall and parted ways with Barbara, she asked us how late we planned to stay.

“You should definitely come to the community dinner,” she told us.

From the community center we could spot the beach, sitting at the bottom of a rolling, green lawn. We picked our way down and took off our shoes where the grass ended and stepped onto the sand.

The beach is squat, perhaps 100 yards long, but large enough to accommodate summer visitors and opens up to a pretty view of Portland’s East End, across the bay.


On the beach we met Alyssa Momnie, playing with her son Mateo. Alyssa lives for most of the year with her family in Massachusetts, but all of the clan are die-hard summer islanders and Alyssa grew up spending summers here.

I asked her what activities she would suggest to visitors of the island.

“I would say jump off the dock,” she told me. “I would say go out in a kayak. I would offer you mine, but my brother just took it out with his friends.” She pointed out at a small group paddling their way toward Peaks Island. “I would say pick some wild blackberries.”

We asked where and she responded: “They’re all over, but I can show you my favorite spot.”

Before we parted ways, Alyssa told us about a path that winds through the woods, making its way across the island, passing by old and decaying military structures, before opening up somewhere inside the Diamond Cove area. “It’s neat,” she said. “You can see parts of the old base.”

“But seriously,” she cautioned us, “be careful when you get over there.”


We decided to run the risk and, walking back over the road we had taken to Elwell Hall, we eventually found an opening in the tall grass of a meadow that matched Alyssa’s description. We walked up the trail cut through the grass until it became a wooded path, and we followed that past old concrete walls and derelict gate posts until we found ourselves on a road in Diamond Cove.

The road was quiet and the area seemed generally empty. Without much reason, we chose to go left down the road and followed it until, by chance, we found ourselves before a picturesque inlet. Here were more people, nicely dressed and in a festive mood, talking loudly and boisterously. Behind us was an enormous green lawn, finely manicured and upon which sat neatly arranged rows of white chairs, all facing an immaculate white gazebo. We heard glasses clinking in the distance. And within the space of a moment we realized we were not only in Diamond Cove, but had stumbled into some area used for receptions, weddings and special functions.

It was, without doubt, one of the prettiest spots we’d found on the island, and we decided to take a load off there, me laying on the verdant grass and Matt sitting in a white Adirondack chair looking out over the inlet. It was midday and we relaxed and basked in the unhindered summer sun. In the hour that we spent lazing about there, we watched as musicians and caterers rushed by chaotically, tanned and portly couples in their 60s sped by on golf carts, and stylish, healthy-looking folks walked casually with their young children up and down the inlet.

As we chatted idly, clouds moved in overhead, threatening our comfort. We grudgingly got up and decided to look for shade. We contemplated walking to the ferry stop at Diamond Cove, where we knew we would find the restaurant and general store. But without truly knowing where we were, we had only a guess as to which direction to go and we slowly, and without reason, began wandering back up the way we had come.

As luck would have it, our problem was solved for us. After walking a few steps, a woman, accompanied by a little dog, appeared ahead of us on the road. Seeing us as she rounded a corner, she came to an abrupt stop and, well, you know the rest. 

We were dropped off, happily for us, right where we had hoped to go, and we waited out the storm in the Diamond Cove General Store. (See the sidebar for information about the general store and Diamond’s Edge Restaurant.) Once the rain passed, we slowly walked the long Diamond Avenue, the only public road connecting both sides of the island. It took us through the old Fort McKinley, offering some unique views of the one-time military base, albeit only from the road. After about 20 minutes, we had arrived back where we had first met Barbara and her friends. We were slightly early for our ferry, and we passed the few moments sitting on the Great Diamond dock, watching boats move swiftly or laboriously across the waters of Casco Bay.


Here’s the take-away: Great Diamond Island is certainly worth the visit, you just have to know where to go. If you’re looking for fine dining, get off the ferry at the Diamond Cove stop and visit Diamond’s Edge Restaurant. If you’re looking for a bit of history, walk along Diamond Avenue through the old military installation (but no touching!). And if you’re looking for a nice beach, good company and to get a sense of the island community, depart the ferry at the Great Diamond stop and head to Elwell Hall and the adjacent beach. Like all places, decorum matters. Be aware of what’s around you and look out for posted signs. If in doubt or if you’re curious, ask a local. Most people on both sides of the island are helpful and friendly, even if they get a bit peeved when you lounge all over their Adirondack chairs.

Or you could always throw caution to the wind and pretend you own the place. It seems that, in the worst case, you’ll get a free golf cart ride out of it.

A house on Diamond Avenue, the main artery which runs across Great Diamond Island.

What to do for a day trip to Great Diamond Island: Suggestions from the experts

Getting there

The trip to Great Diamond Island takes 20 to 25 minutes by ferry on the Casco Bay Passenger Ferry terminal at 56 Commercial St. in Portland. A round-trip ticket at peak season (April to October) is $9.25 for adults and $4.60 for children, seniors and riders who present a Medicare card, METRO Reduced Fare card or an out-of-state disability card issued by a transit agency. Children under 5 are free. In the summer, the ferry departs at least eight times a day.


Going and doing

Our volunteer tour guide, Barbara Raimondi, gave us these suggestions:

* Go for “a complete walk around the island” to see the picturesque scenery and views of Casco Bay. Just watch for posted signs, since much of the island is off limits to visitors.

* Go to the beach. “There are nice beaches on both sides. There’s a sea glass beach on the Diamond Cove side,” just below the Diamond Cove dock. But, Barbara says, “because there’s private property on the Cove side, they’re not always as friendly with people walking around.” You can also visit the beach at Elwell Hall. “Nobody will bother you” there, says Barbara. To get there, get off the ferry at the Great Diamond stop (not Diamond Cove), walk straight down the dock and continue on Nancy Lane. Take your first left on Waymouth Street and hang a right onto Spring Avenue when the road ends. At the end of Spring, turn left onto Crescent Avenue and you’ll quickly arrive at Elwell Hall, a very large brown building with beige trim and a ramp leading up the front door.

* Biking is great.” But again, watch for posted signs.

* See the old Fort McKinley. “Go over to Diamond Cove and see all the parade grounds,” but stay on Diamond Avenue. (Do we really have to keep reminding you?)


* Go kayaking. This one is tricky unless you’ve come over by kayak or know someone on the island who is willing to lend. But, says Barbara, “it’s a great place for kayaking. It’s a great kayak (trip) around Great Diamond. It’s a great kayak (trip) around Little Diamond. It’s a great kayak (trip) over to Fort Gorges. And it’s a great kayak (trip) over to Peaks along the coast and then around House Island and to Fort Scammel.” Heads up, that last one makes for a very long trip.

* Visit Little Diamond Island. If you’re visiting Great Diamond at low tide, you can walk across the sandbar to Little Diamond Island. Little Diamond, also part of the city of Portland, is primarily private. However, the roads are public and offer a nice circuit for walking or biking.

Eats and shopping

* The Elwell Hall community store, located in the basement of Elwell Hall on Crescent Avenue, is open in the summer. The hours are sporadic. “If you come out during the week,” says Barbara, “the store would probably be open. But there’s no guarantee, since it runs on volunteers.” It sells provisions, sweets, cold drinks, books and material related to the island. Get more info online at: https://www.facebook.com/TheStoreAtElwellHall.

* The Diamond Cove General Store, located a few hundred feet from the ferry stop at Diamond Cove on Diamond Avenue, sells hot and cold sandwiches and other snacks and fixings, provisions and souvenirs. It is open daily from 7 a.m. to 8 p.m. in the summer and off-season Thursdays through Sundays from 7 a.m. to 8 p.m. Get more info online at: http://dcgeneralstore.wordpress.com/.

* For fine dining, visit Diamond’s Edge Restaurant and Marina, located adjacent to the Diamond Cove dock on Diamond Avenue. It is currently open Tuesdays through Sundays, serving lunch from 11:30 a.m. to 2:30 p.m. and dinner from 5:30 to 9:30 p.m. It is open seasonally with varying hours. To see the hours, menu, or for more info visit their website at: http://diamondsedgerestaurantandmarina.com/.


Reliable public restrooms may be difficult to find on Great Diamond. A number of the folks we met at Elwell Hall community center let us know that visitors are welcome to use the restroom there, but as that may not always be open they suggested trying Diamond’s Edge Restaurant in a pinch.

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