Community and Lifestyle on the Casco Bay Islands: Five Very Different Neighborhoods
"The Casco Bay Islands" is not one community -- it is five, and they do not share a single identity just because a Casco Bay Lines ferry connects them all to Portland. Long Island incorporated its own town government by breaking away from Portland; Chebeague Island did the same thing to a neighboring town, for a completely different reason; Great Diamond Island's Diamond Cove neighborhood is a converted 19th-century fort; Little Diamond Island is close to empty most of the year; and Cliff Island, despite having barely sixty year-round residents, runs a real civic and school life on unpaved roads. Peaks Island -- the largest, most populous, and most-served of the Casco Bay islands, with its own commuter-ferry identity and its own pending secession bill against Portland -- is covered in depth on this site's dedicated Peaks Island pages and is mentioned here only as context, not as part of this page's subject. This page treats the other five islands honestly, one at a time, including being upfront about where a "community" is thin or seasonal rather than padding out islands that genuinely do not have much going on twelve months a year.
Five Islands, One Ferry System, Five Different Stories
Long Island, Chebeague Island, Great Diamond Island, Little Diamond Island, and Cliff Island are all reached by Casco Bay Lines from downtown Portland, and Chebeague is also reached by a second operator, the Chebeague Transportation Company, running a shorter route from Cousins Island in Yarmouth. Sharing a ferry system is close to the only thing these five islands have in common. Long Island and Chebeague Island are each their own incorporated Maine towns, having seceded from larger municipalities for genuinely different reasons. Great Diamond, Little Diamond, and Cliff Island remain part of the City of Portland and never had a secession story of their own. Year-round population runs from Chebeague's 396 residents (2020 Census) down to Little Diamond's five residents at the 2000 Census -- a range wide enough that treating these five islands as a single interchangeable "island lifestyle" would flatten out exactly what is most useful to understand about each one.
That range matters for anyone actually comparing these places rather than just admiring them from a ferry rail. A community built around a two-room elementary school and two separate ferry operators (Chebeague) is a fundamentally different proposition than a mostly-vacant seasonal cottage colony where the water gets shut off every winter (Little Diamond). This page goes island by island rather than blending them into one composite picture, because the honest answer to "what is community like out here" is different depending on which dock you actually step off of.
Long Island: A Town Built By Pushing Back Twice
Long Island's community identity runs through a real act of local self-determination: on July 1, 1993, Long Island seceded from the City of Portland and became its own incorporated town. The separation followed Portland's 1990 property-tax revaluation, which sharply raised taxes on the island; residents argued the burden was out of proportion to the municipal services the island actually received. That is a genuine, documented tax-and-representation grievance -- islanders concluding that a distant city government was taxing them without delivering commensurate services, and choosing to run their own town instead.
It was not the island's only fight against outside pressure. In 1969, King Resources proposed building a supertanker port on or near Long Island -- a proposal that did not go forward. Three years later, in 1972, the tanker Tamano spilled oil that contaminated the island's West Beach, a real and documented environmental incident, not a hypothetical risk. Together, the defeated supertanker-port proposal and the Tamano spill give Long Island a second, separate throughline alongside its 1993 secession: a community that has, more than once, pushed back against outside industrial and fiscal pressure it didn't ask for. As of the 2020 Census, Long Island's year-round population was 234, with roughly 225 registered voters as of March 2025 and a summer population commonly described as swelling to 800 to 1,000 -- a three-to-four-times seasonal multiple that shapes the island's rhythm the way it does across most of this group. The island maintains its own Long Island School, though this page did not independently confirm the grade range it serves.
Chebeague Island: The Most Full-Service Community of the Five
Chebeague Island is both the largest and the most self-sufficient of these five communities. At 396 year-round residents (2020 Census, a 16% increase over 2010), it has more full-time neighbors than Long Island, Great Diamond, Little Diamond, and Cliff Island combined. Chebeague Island seceded from the town of Cumberland, Maine on July 1, 2007, after 184 years as part of that town -- a real secession authorized by the Maine Legislature via a specific public law (PS Law, Chapter 47), following a statewide legislative vote on April 5, 2006 that passed the Maine Senate 31-3 and the House 131-1. Unlike Long Island's tax-revaluation grievance, Chebeague's secession was driven primarily by a different motivator: protecting the island's own small elementary school from downsizing pressure inside the larger Cumberland school district. Community life here is genuinely organized around keeping that school -- and the island's own two-room schoolhouse, serving pre-K through fifth grade, still anchors daily life for island families, with students in sixth grade and above commuting by ferry to mainland schools.
Chebeague is also the only island in this group served by two separate ferry operators: the Chebeague Transportation Company runs a roughly 15-minute passenger crossing from Cousins Island in Yarmouth to the island's Stone Wharf, plus a vehicle and freight barge April through November by reservation, while Casco Bay Lines runs a longer, roughly 60-to-90-minute mail-boat route from downtown Portland to Chandler's Cove wharf. That two-route, two-operator structure is unique among these five islands and gives Chebeague residents an off-island option -- Yarmouth -- that the other four don't have. The island's community infrastructure runs deeper still: the Museum of Chebeague History, a year-round taxi service, and the Great Chebeague Golf Club, a nine-hole course founded in 1920 whose clubhouse is a repurposed circa-1807 residence, moved to its current site in 1928 and listed on the National Register of Historic Places on July 14, 2015. At low tide, Chebeague connects on foot to the smaller, state-owned Little Chebeague Island, part of the Maine Island Trail system -- a tidal-sandbar connection none of the other four islands has. Put together, Chebeague reads less like a remote outpost and more like a small, complete, self-governing New England town that happens to be surrounded by water.
Great Diamond Island: A Fort Turned Into a Neighborhood
Great Diamond Island's defining community feature is Diamond Cove -- and Diamond Cove is not an organic small-town settlement the way Long Island's or Chebeague's village centers are. It is a converted military fort. Originally known as Great Hog Island and home to a 19th-century artistic retreat (Henry Wadsworth Longfellow and Harriet Beecher Stowe are both associated with it), the island became the site of Fort McKinley, built roughly 1897 to 1906 and eventually covering 111 acres with nine gun batteries -- described as Casco Bay's largest military installation. The fort closed in 1947 and was sold to private interests in 1961; the Fort McKinley Historic District was listed on the National Register of Historic Places in 1985. Diamond Cove today is the redeveloped result: former army barracks and officers' quarters converted into private homes, organized as a gated, mostly private residential community with the Diamond Cove General Store and Diamond's Edge Restaurant & Marina as its public-facing businesses, along with the Inn at Diamond Cove.
That makes Great Diamond's community character genuinely different from Long Island's or Chebeague's -- more planned, more built, and organized around a single historic-preservation-and-redevelopment real estate project rather than generations of an organically grown fishing village. Great Diamond's year-round population is itself an unresolved figure worth stating honestly rather than picking a number: Wikipedia cites 77 residents at the 2000 Census, while a more recent commercial demographics source shows a much smaller current snapshot of 12 residents and 6 occupied households, a gap this page cannot reconcile with confidence. Either way, Great Diamond does not have its own secession story -- it has remained part of the City of Portland throughout, unlike Long Island and Chebeague.
Little Diamond Island: Honest About How Little "Community" There Is
Little Diamond Island deserves a direct, unpadded answer to the question "what is community life like here": there mostly isn't one, most of the year. At the 2000 Census, Little Diamond had five year-round residents, a figure explicitly attributed to the island's water supply being shut off in winter, which limits permanent habitation. A more recent commercial demographics snapshot shows an even smaller picture -- two residents and one occupied household out of three total housing units, two-thirds of them vacant. Little Diamond, formerly known as Little Hog Island, remains part of the City of Portland; it never had a secession story, and this page did not find a school, a dining establishment, or any organized civic institution on the island.
That is not a gap in this page's research -- it is an honest description of what Little Diamond actually is: a small, predominantly privately owned seasonal-cottage enclave that functions as a vacation retreat rather than a year-round neighborhood. Anyone drawn to the idea of a quiet, private island retreat should read that as a real feature, not a shortcoming -- but anyone picturing a functioning year-round community, a school run, or a local civic calendar the way Chebeague or Cliff Island have them should recalibrate that expectation specifically for Little Diamond.
Cliff Island: A Tiny Population Running a Real Civic Life
Cliff Island is the clearest counterexample on this page to the idea that a small year-round population means a thin community. At roughly 60 year-round residents as of the 2000 Census (swelling to about 200 in summer), Cliff Island is genuinely small -- and yet it runs a one-room school serving pre-K through fifth grade (roughly six students as of a 2020 profile, a figure worth re-verifying before treating as current), a 100-plus-year-old island library, a tennis court, a baseball field and playground, a summers-only Historical Society museum, and an active, all-volunteer community organization known as ACE -- covering athletics, conservation, education, arts and crafts, and entertainment -- that runs the island's event calendar. The Cliff Island Association Hall completed a renovation in 2020. Older students, as on Chebeague, commute daily by ferry to mainland schools once they age out of the island's own classroom.
Cliff Island is also the only year-round-inhabited island in this group with entirely unpaved roads -- residents get around by walking, bicycle, and golf cart rather than by car, and extensive conservation land protects that rural, car-free character. It sits at the end of the longest Casco Bay Lines run of the five, commonly cited at roughly 60 to 120 minutes one-way depending on route and freight stops, with five daily round trips operating year-round. Casco Bay Lines itself describes Cliff Island as "the smallest year-round inhabited island in Casco Bay," a claim that sits in real tension with Little Diamond's even-smaller population figures above; this page states both facts rather than declaring one island definitively smaller, since the honest explanation is likely that Little Diamond functions as a private seasonal retreat while Cliff Island has a genuine, organized, year-round civic and school life that Little Diamond does not.
What All Five Islands Are Dealing With Right Now
Despite their differences, these five islands are living through the same two civic stories in 2026, and both are worth understanding before assuming island life here is simple or static. The first is a live fare dispute over the ferry system every one of these communities depends on for groceries, mail, medical trips, and building materials. Casco Bay Lines proposed raising peak-season round-trip adult passenger fares from $14 to $17 -- a 21% increase, the second passenger fare hike in three years -- citing rising fuel, labor, maintenance, and insurance costs. Hundreds of island residents filed a formal petition over affordability and notice concerns, and on June 16, 2026, the Maine Public Utilities Commission unanimously voted to open a full, formal investigation into both the financial justification for the increases and the rate-setting process itself, with the new fares remaining in effect for the summer season while that investigation proceeds. Separately, Casco Bay Lines' own current rates page lists a peak-season round-trip adult fare of $16.00 (child, senior, and disabled fare $8.00) and an off-peak round-trip adult fare of $8.00 -- flat rates applied identically across all seven stops the line serves, meaning the roughly two-hour round trip to Cliff Island currently costs the same as the short hop to Peaks Island. The exact relationship between the $17 figure discussed in the proposal and the $16 figure on the carrier's current rates page was not resolved in this page's research; treat the carrier's own site as the more current source and re-verify before relying on either number.
The second live story is a documented island-housing-affordability crisis. A July 2025 Portland Press Herald investigation into Maine's 15 unbridged islands -- explicitly naming Chebeague, Long Island, and Cliff Island among the Casco Bay islands examined -- found a median island resident age of 56 versus 44 statewide, housing costs pushed up by wealthy outside buyers converting year-round homes to seasonal use, island construction costs running roughly 30% higher than mainland costs due to barge transport, and land supply constrained by conservation easements. On Chebeague specifically, the Chebeague Island Community Association has run real, named affordable-housing projects for over a decade: a modular duplex at 43 School House Road, built with a $350,000 MaineHousing grant and installed in May 2012; a 2013-2014 rent-with-option-to-purchase house at 226 South Road; and a second modular duplex at 553 South Road, installed in May 2025 on land donated by Stacie and Toby Webb, with tenants expected to move in during fall 2026. On Cliff Island, converting single-family homes to multi-unit rentals has been tried as a response to the same pressure. No comparable current civic story specific to Great Diamond or Little Diamond Island was found in this page's research -- both islands' small, seasonal populations appear to draw less standalone press coverage than their three neighbors.
What This Means Before You Decide
Put together, honestly: "the Casco Bay Islands" is really five separate answers to the question of what community life looks like out here. Long Island is a town that broke away from Portland over taxes and has weathered a real environmental scare. Chebeague is the closest thing to a complete, self-sufficient small town, organized in large part around keeping its own school and served by two separate ferry operators. Great Diamond's Diamond Cove is a historic fort rebuilt into a planned residential community, not an organic village. Little Diamond is, honestly, closer to empty than to a neighborhood most of the year. And Cliff Island proves that a tiny population and a genuine, organized civic life aren't mutually exclusive. All five currently sit inside the same live ferry-fare fight and the same regional housing-affordability crisis -- shared pressures riding on top of five otherwise distinct identities. Peaks Island, the sixth and by far most populous Casco Bay island, has its own separate commuter-ferry identity and its own pending secession question, covered in depth on this site's dedicated Peaks Island pages rather than here.
None of this is offered to sell any one of these islands over another -- it's the real, differentiated shape of community life across five places that get lumped together far more often than they should be. Before making any move, verify current Casco Bay Lines and Chebeague Transportation Company schedules and fares directly with those carriers, check the current status of the Maine Public Utilities Commission's fare investigation, look into each town's own governance directly -- townoflongisland.us and townofchebeagueisland.org for the two incorporated towns, or the City of Portland's own channels for Great Diamond, Little Diamond, and Cliff Island -- and talk to current residents about what year-round life is actually like on whichever island you're considering. Nothing on this page is legal, civic, or relocation advice.
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Get a Free Agent Referral →Independent research. No ads. No sponsored listings. Long Island's July 1, 1993 secession from the City of Portland, following Portland's 1990 property-tax revaluation, and Chebeague Island's July 1, 2007 secession from the town of Cumberland (authorized by Maine PS Law Chapter 47, following an April 5, 2006 legislative vote of Senate 31-3 and House 131-1) are both documented via Wikipedia and the Island Institute. The 1969 King Resources supertanker-port proposal and the 1972 Tamano oil spill at Long Island's West Beach are documented via Wikipedia. Fort McKinley's 1897-1906 construction, its 1947 closure, and the Fort McKinley Historic District's 1985 National Register listing are documented via Wikipedia. The Great Chebeague Golf Club's 1807 clubhouse and its July 14, 2015 National Register listing are documented via Wikipedia. Population figures (Long Island 234, Chebeague 396, Great Diamond 77, Little Diamond 5, Cliff Island approximately 60) are 2020 or 2000 Census figures as cited by Wikipedia; more recent commercial demographic snapshots for Great Diamond and Little Diamond diverge meaningfully from these Census figures and both are stated here rather than resolved. The 2026 Casco Bay Lines fare-increase proposal, the resulting Maine Public Utilities Commission investigation opened June 16, 2026, and the carrier's own current passenger rates are documented via the Portland Press Herald, Maine Public, WABI, and Casco Bay Lines' own rates page; the relationship between the proposed $17 fare and the carrier's current $16 fare was not resolved and should be re-verified directly with Casco Bay Lines. The July 2025 Portland Press Herald investigation into Maine's unbridged-island housing crisis, and the Chebeague Island Community Association's specific housing projects, are documented via the Portland Press Herald and the CICA's own website. This page does not state a specific current ferry fare, population figure, or business name as guaranteed current and unchanging -- verify all such details directly with Casco Bay Lines, the Chebeague Transportation Company, each island's town government or the City of Portland, and current residents before making any moving or purchase decision. Nothing on this page is legal, civic, or relocation advice.