The Working Waterfront

The serendipity of island life brings joy

We’re reminded, often, of out tight connections

BY GRACE UPHAM
Posted 2025-11-04
Last Modified 2025-11-04

Reflections is written by Island Institute Fellows, recent college grads who do community service work on Maine islands and in coastal communities through the Island Institute, publisher of The Working Waterfront.

Island Serendipity (n.): fateful occurrences that would be unusual, even unbelievable, in some contexts but are almost inevitable in a close-knit community.

I first crossed the Deer Isle-Sedgwick suspension bridge on a frigid February afternoon, the eve of my interview for the Deer Isle fellowship position. Aiming to acquaint myself with the island and some community members ahead of time, I was also taking the opportunity to visit another part of the region I’d recently made home.

Admiring the snow-ringed ocean inlets as I meandered down Route 15 to Stonington at the island’s southern end, I tried to keep my hopes in check but couldn’t help imagining my life here.

I couldn’t have predicted that I’d soon be gripping the gunwale of a lobster boat, cheering and shouting alongside a lobstering family…

Discovering my destination museum shut for the season put a damper on my daydreams. Despite pivoting to lunch at the one open restaurant and the waiter’s encouraging “welcome home” after our brief chat, I still felt defeated by my poor planning and sparse opportunities for further social headway.

Giving up on even a walk in the intense cold, I was deciding to just drive back to Mount Desert Island when someone called across the street, “Were you that artist painting at the end of the pier earlier?”

I quipped back, “I wish, but no!” and then leapt out of my comfort zone to introduce myself. Converging in conversation, we discussed our lives and work, and he emphasized how different Deer Isle was from MDI.

GRACE UPHAM
GRACE UPHAM

Thanks to the waiter’s welcome and this spur-of-the-moment encounter, I crossed back to the mainland with a developing sense of how an aspiring resident might achieve belonging and an even greater desire to call this island home. During my second interview, my now fellowship advisor called this chance meeting island serendipity.

Serendipitous connections are invaluable in my fellowship work developing and marketing Deer Isle Adult and Community Education (DIACE) programming. Besides providing an easygoing space for high school completion and various career development resources, we run an eclectic schedule of life-enriching classes encompassing industrial arts, multi-media crafts, mental health support, outdoor recreation, and more.

But in a community with limited free time and established habits and social circles, inspiring people use our services requires maintaining a word-of-mouth network with trusted islanders. While I built relationships with a range of community members in my first months, too few of them represented Deer Isle’s fishing workforce.

It took a last-minute tabling task on behalf of a DIACE partner to finally kindle these missing connections and set in motion my favorite fellowship experience to date.

Bleary-eyed on a foggy July morning but at least enjoying quality time with my wonderful tablemate, Stacey, I couldn’t have predicted that I’d soon be gripping the gunwale of a lobster boat, cheering and shouting alongside a lobstering family and an entourage of journalists as we barreled 45 mph past the harbor.

As the channel cleared of mist and the Stonington Lobster Boat Race contestants geared up, my desire for a relaxing Sunday lifted with the fog. I was seeking out a waterside vantage point for the action when Stacey suggested she could do me one better.

Just before it was too late, she shouted down the gangway to the race organizers: “Have you got room for one more?” The moment I climbed aboard, I was welcomed with a hug and the announcement that, “When you’re on our boat, you’re family”.

Such instantaneous generosity, both from this family and Stacey, reminded me of my formative Stonington encounters and reinforced how lasting connections can form in serendipitous blinks-of-an-eye.

Most valuably, the unforgettable day encapsulated what I couldn’t fully articulate that February: to belong here means mindful, respectful participation in Deer Isle’s deep-rooted values and heritage. And although I paid for my spontaneous four-hour excursion with a nasty sunburn, I had the time of my life racing.

Grace Upham is providing marketing, administrative, and strategic support for Deer Isle Adult and Community Education focusing on expanding its brand, network, reach, and variety of classes.