Island Hopping in Maine on a Mailboat.

Mailboat Docked for the night, Portland Harbor.

On an unusually hot spring day we took a mailboat out of Portland, Maine recently. The mailboat runs through five islands in Casco Bay. We pushed back from the ferry docks at Portland Harbor sharp at 10 in the morning. The boat was loaded with mail, boxes, and carts full of packages and shopping bags. My mind took time to imagine what those carts must be carrying for the few hundred residents of each of the islands the boat visits. The excitement was high amongst us tourists and day trippers. The sea breeze made a hot day somewhat bearable. The locals sought the interiors and benches under the shade indifferent to the beauty of the Maine coast passing by us. The captain gave us a brief introduction of our run and on the way to each island gave us a brief introduction of the island. We became part of the history of mail drops by the mailboat for last 150 years. There are 3 mailboat runs per day and they make stops at Little Diamond Island, Great Diamond Island, Diamond Cove, Long Island, Cliff Island, and Great Chebeague Island. As we dropped off the mail and picked up the passengers, we also became the observers of stories that unfolded in front of our eyes.

We watched as the Portland skyline and the light houses receded behind us. We admired Fort Gorges as we passed by it. The first stop was Little Diamond Island. This island was still close enough for us to see Portland in the distance. The dock was empty. We stopped there and a crew member pushed a cart with a few packages onto the dock and left it there. There seemed to be no one to collect the cart. A lonely cart sat there with the daily needs of the summer residents of this tiny island as we pushed away and made our way to the Great Diamond Island. The tide was low so we could see the sandbar that connects these two islands. 

Mail Drop

We made a quick stop at The Great Diamond dock to drop off a passenger. There was a small welcoming party waiting to receive her and she was enveloped in a warm hug of an older woman. A daughter returning home? I wondered! As we pushed out, the little group on land was so engrossed in catching up that they barely noticed the mailboat and its passengers slowly moving away. There are very few roads on this island so people depend on golf carts and bikes to get around. The residents are mostly only there for the summer.

A reunion

We made our way to the other side of Great Diamond Island to Diamond Cove. It’s home to Fort Mckinley. The  army barracks and officers’ housing on the island have been converted into homes. There is an Inn at Diamond Cove for the tourists who want to enjoy island life. A white painted school bus was waiting to take the packages from our boat. A lady with her 2 plants got off. A mainland purchase of two little plants to be planted in the garden of her home I thought. A camera crew came along. Maybe they there to shoot an episode for a travel show!

Diamond Cove drop

In between the islands of the Casco Bay life went on.  A barge slowly glided across the water, a water taxi sped towards one of the islands, a big cargo ship was idling on the water for its turn to dock, a lobster boat with the crew dumped the lobster traps in the water, a coast guard boat painted with the logo of 250 years of America waited while we passed by and few colorful canoes came oaring next to us. 

Canoes

There are many tiny islands around which we navigated. A rich man’s private island, a tiny rock island with a single home atop, a barren rocky island jutting out from the sea. Some inhabited while others uninhabited. The temperature on the bay near the islands was a few degrees cooler. The sun was now hiding behind the white scattered clouds. 

A home on Chebeague Island

We navigated around all these to dock at Long Island. It’s a popular destination for tourists. There is a vibrant community here that works in the lobster industry year around. Many day trippers got off here. A lot of them seem to be heading to Sandy Beach on the island, carrying their picnics along. A man with shovels had come on board with us in Portland. He got off here. The captain of our boat told us about the schooling of the children on these islands where there are full year residents. They all go to school on the mainland after the 5th grade. A long school day for these kids. They go to and from the schools on the ferry services. I can imagine the middle and high schoolers sitting inside on a table to finish their homework or catching up on some sleep during the long school commute. 

Mail Drop on Long Island

Cliff Island was next. A man was sitting with a lawnmower on our boat. He read a hard bound book throughout the journey holding onto his lawnmower with one hand and book with the other. Finally he had reached his destination. He pushed the lawnmower out on the dock as he disembarked and disappeared behind the dock house. I wondered why he was on the boat with a lawnmower.

A family was waiting for us in a huddle. The cargo was being pushed out on the carts. The family waited. The goodbyes needed to be said and the hugs were to be given. Let the crew finish unloading the carts. Let them have the final minutes to say goodbye. As the young family came on board, the grandparents rushed forward on the dock waving away the grandkids with both hands and flying kisses were exchanged. When will they see each other I wondered! In the background there was the Cliff Island Store and Cafe. Maybe the grandparents would go to the store, pick up the couple of things they needed and would sit down at the cafe to have coffee and reminisce about their children and grandchildren’s visit. 

Saying Goodbye

The mailboat routine was smooth as we reached each island. As we approached the dock, within a blink of an eye the dock line was thrown to the bollards on the dock to anchor the boat. The bridge is connected to the dock for the passengers to disembark and cargo carts to be pushed out. First the passengers go out and then the cargo. If people were coming on board they would come next. Not a minute got wasted. Everything went like clockwork. Rarely we saw cargo coming on board. All we saw was people’s luggage being brought in when they came aboard. Many times I tried to capture the clock work precision of docking but before I could focus, it was done. Everything was precise and with the economy of movement!

Departing

The boat approached the Chebeague iIsland. There were a couple of cars waiting to haul away the cargo. There was a big cart of boxes to be taken down from the top deck. I saw the arm of a crane extend to bring down the cart to the dock. Three men rushed to the cart as soon as it was laid on the dock. They were eager to check out the contents. The boxes were for Chiquita bananas but I think they contained anything but. I saw a cooking oil bottle as it was removed. Maybe the goods were for a general store on the island or they were supplies for a restaurant or was it to begin a home for the summer season? I imagined every scenario! 

Arrival of Grocery at Chebeague Island

Now there was no more cargo to be distributed or passengers to disembark. The only people on the boat were a few tourists like us who were there for the ride and to experience the working of a mailboat. We stopped at two of the islands we had stopped earlier, this time we took passengers on. The first one to come back to the boat was the guy with the shovels. He must have finished his work on the island to come back on the boat for its return journey to Portland. How life revolved around the mailboat’s runs for these workers shuttling between the mainland and the islands. These were locals who came on board. The boat suddenly became a gathering place. The sound of the lapping water, the clang of the bayous and the hum of the engine hid under the excited chatter. They all seem to know each other. They were catching up with each other. There was a visiting nurse with them, who they all seemed to know. We heard her talk about visiting the island every two weeks or so. A nurse giving medical care to the islanders who were too sick to travel to Portland!

Cliff island store and cafe

We saw the Portland skyline slowly becoming more visible in the afternoon heat. We were approaching the Portland ferry terminal after 2 and a half hours of mail and passenger drops. We brought with us the passengers who had come to the mainland to do their shopping, or visit with a friend or have a bite at one of the nice restaurants in Portland. My imagination had worked overtime. Stories were written at every island stop and my imagination took over as each story happened. The people and the lives on these islands became characters and events in my head. I observed and became a part of this simple island life for a brief period. The simplicity of life in the lap of nature was all that mattered. 

Notes: Casco Bay mailboat leaves from Portland ferry terminal on 56 Commercial Street, Portland, Maine. There is a municipal parking structure next to the terminal. The mailboat ride can be 2:30 to 3 hours depending on the mail drops and number of passengers. If you go, pack your own water, drinks and snacks. There is no food or drinks available on board. There are three departures everyday, 10 AM, 12 PM and 3 PM. Tickets are $21 for adults, $17.50 for seniors and $12 for children.

Published by Neha Shah

Hi! I love to travel, I love art and architecture, I enjoy cooking, and, more recently, I've been bitten by the photography bug. My family has always respected my need to explore and observe the world outside the window. They always leave the window seat for me, be it in a car, train, or plane. They are always walking along side me when I am out exploring. I am shy by nature so I guess I am happiest when I see, observe, and imagine. When we moved to London, it was a dream come true. This city was one I read about in books and dreamed about as a child. I had visited it many times as an adult before we actually moved here, but being part of the life here has brought me out of my inertia and made me pick up the pen again. My ever present phone helps me capture the images of what I see. One fine day my pen and phone made me sit down to write my first blog post!

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