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Finding Chebeague By Eric Norcross
People often imagine that living on an island is inherently idyllic—a postcard just waiting to be lived in. But islands are honest places. Anyone who has grown up on an island knows better. There are challenges woven into every errand, every storm forecast, and every ferry schedule change. For all the beauty and quiet, islands demand patience, flexibility, and a willingness to meet the tides on their terms. I grew up just across the sound, so I understood this long before we arrived on September 1st—our official move-in date for our relocation to Chebeague. Jan and Sophie, although familiar with most of the inhabited Casco Bay islands, hadn’t yet lived through a full season on one. Still, they were eager to try. What brought us wasn’t escapism, but the hope of building a life for our daughter, Sophie, that felt grounded, connected, and human in a way that seemed increasingly difficult to find in many mainland communities. Chebeague had lived at the edge of my imagination for years— familiar from a handful of school trips and from its recurring presence in some of my father’s most interesting memoirs—yet personally, I had never truly explored it. That changed in the summer of 2023, when my film 43 Degrees North went into pre production. The project gave me the chance not only to scout the island in depth, but to shoot scenes here as well. Through that project, I came to know the island—and many of its creative people. We returned often, first for holiday dinners, then for
Whalers concerts, and a remarkably sophisticated community theater production of South Pacific (one that rivals many off Broadway shows I’ve seen over the years). While all the islands draw exceptional artists across many disciplines, Chebeague, I discovered, is the only down-bay island with a deep performing arts soul. I felt drawn back again and again. To my delight, Jan and Sophie took to island life even faster than I did. Sophie had long considered Chebeague a part of her home, having grown up with the film and the many events we attended here over the years. Jan, however, grew up on Manhattan’s Upper West Side, and convincing her to move to Maine was one of the hardest things I’ve ever done—she had every reason to expect that island life might feel like a stretch. And yet, after her most recent trip to New York to visit family, all she wanted was to “return home” to Chebeague. (I admit I’m sitting here smiling as I type that.) What has struck me most since relocating is how full of life the island feels: the number of families here, the vitality of the school, and the ease with which essential resources—like the Kids’ Place—are woven into daily life. Chebeague has found a way to remain connected, resilient, and deeply supportive of those who call it home year-round. It’s an island that demonstrates what can happen when a place is treated not as a commodity, but as a community we actively steward together.
As we look ahead to the New Year, it’s the perfect time to get an updated real estate review of your home. The value of your property can fluctuate year to year with the market. If you’re curious about what your home is worth, reach out today for a confidential, no-obligation home valuation. Cheers to 2026!
The Leonard Thompson Federle Team Your Island + Mainland Specialists
Karen Thompson 207.329.6729
Jodi Federle 207.215.4006 office: US Rte 1, Falmouth
Jane Leonard 207.831.9951
email: ltf@portsidereg.com
JANUARY 2026 CHEBEAGUE ISLAND COUNCIL CALENDAR
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