Things to Do on the Other Casco Bay Islands: Golf, a Ruined Fort, and Genuine Quiet

Island-Hopping by Ferry Is Itself the Main Attraction

Casco Bay Lines runs passenger service out of downtown Portland to all five of these islands, and for most visitors, simply riding the boat from stop to stop is a genuine activity rather than just transportation. Long Island trips typically run 30 minutes to an hour; the run to Chebeague Island's Chandler's Cove wharf takes roughly 60 to 90 minutes; and Cliff Island, the farthest of the group, is the longest ride of all -- commonly cited at 60 to 120 minutes one-way, with five daily round trips operating year-round.

Chebeague Island is the one genuinely different case: it has a second, separate ferry operator alongside Casco Bay Lines. The Chebeague Transportation Company runs a short, roughly 15-minute passenger run from Cousins Island in Yarmouth to the island's Stone Wharf, plus a vehicle and freight barge from April through November by reservation -- a faster, more direct route than the longer Casco Bay Lines trip from downtown Portland. That two-operator, two-route setup is unique among these five islands.

On fares: Casco Bay Lines' own current rates page lists a flat round-trip adult fare that applies identically to all seven stops it serves (Peaks, Little Diamond, Great Diamond, Diamond Cove, Long, Chebeague, and Cliff), regardless of distance -- meaning the two-hour trip to Cliff Island costs the same as the short hop to Peaks Island. Fares have risen twice in the past few years and were, as of mid-2026, under a formal Maine Public Utilities Commission investigation into both the increases and the rate-setting process. Confirm current fares and schedules directly with Casco Bay Lines (and, for Chebeague, the Chebeague Transportation Company) before planning a multi-island day.

Chebeague Island: A National Register Golf Clubhouse, a Historic Inn, and Paddling to Little Chebeague

Chebeague Island, the largest of these five, has the fullest short list of things to do in the group. The Great Chebeague Golf Club is a nine-hole course on the island's north side -- founded in 1920 as a six-hole course and later expanded to roughly 28 acres, with water views from every hole. Its clubhouse is the genuine standout: a repurposed circa-1807 residence, described as probably one of the oldest buildings used for that purpose in the nation, relocated to its current site in 1928 with a wraparound porch added in 1935. It was listed on the National Register of Historic Places on July 14, 2015.

The Chebeague Island Inn offers fine dining with sunset views and is as much a destination in its own right as a place to stay or eat -- a genuine anchor for an island with a thin roster of businesses overall.

The waters around Chebeague are part of a real paddling landscape: at low tide, Chebeague connects on foot to the smaller, state-owned Little Chebeague Island, which is itself part of the Maine Island Trail, a route used by sea kayakers exploring Casco Bay's islands. Confirm current conditions, tide tables, and any access rules before planning a paddle or a walk out to Little Chebeague, since none of those specifics were independently confirmed for this page.

Great Diamond Island: Fort McKinley's Ruins, Diamond Cove, and an Artists' Retreat Before the Army Arrived

Great Diamond Island's identity is genuinely singular among these five islands. Originally known as Great Hog Island, it was a 19th-century artistic retreat -- Henry Wadsworth Longfellow and Harriet Beecher Stowe are both associated with it -- and it had its own nine-hole golf course before any of what came next.

What came next was Fort McKinley, built roughly 1897 to 1906 into what became Casco Bay's largest military installation: 111 acres with nine gun batteries split between north and south forks. The Fort McKinley Historic District was listed on the National Register of Historic Places in 1985. The fort closed in 1947 and the Navy sold the site to private interests in 1961.

Today the former fort is Diamond Cove, a redeveloped, gated, mostly private residential community built from converted army barracks and officers' quarters. Its public-facing businesses are limited but real: Diamond's Edge Restaurant & Marina and the Diamond Cove General Store, plus the Inn at Diamond Cove for overnight stays. This is a different fort and a different story than Peaks Island's Battery Steele -- visitors interested in that WWII-era site should look to this site's own Peaks Island page.

Cliff Island: No Cars, No Pavement, Real Quiet

Cliff Island is the only year-round-inhabited island in Casco Bay with entirely unpaved roads -- residents and visitors get around on foot, by bicycle, or by golf cart, not by car. Extensive conservation land protects the island's rural, undeveloped character, and the island's H-shaped, remote geography, combined with the longest ferry ride of the group, makes it the quietest and least-visited of the five.

Civic life here is real but small: a library more than 100 years old, a tennis court, a baseball field and playground, a summers-only Historical Society museum, and an active, all-volunteer community organization known as ACE (athletics, conservation, education, arts and crafts, entertainment) that runs the island's event calendar. The Cliff Island Store & Cafe, a seasonal store-and-cafe combination, is the island's evident sole dining option -- there is no other restaurant to point to here, and that thinness is part of the island's honest character rather than a gap to paper over.

Long Island: Beaches, a Hard History, and a Town That Fought for Itself

Long Island has real beaches, including West Beach -- though West Beach's most notable chapter is a grim one rather than a recreational one: in 1972, the tanker Tamano ran aground and spilled oil that contaminated the beach, a documented environmental event from the island's history rather than a current draw.

The island's other defining feature is civic, not scenic: Long Island seceded from the City of Portland on July 1, 1993, becoming its own incorporated town after Portland's 1990 property-tax revaluation sharply raised taxes on the island relative to the municipal services residents felt they received. That secession, decades before Peaks Island's own still-pending secession bill against Portland, is a genuine point of local pride and identity on Long Island today -- a small town that pushed back and made its independence stick.

A Quick Word on Peaks Island

Peaks Island is the largest, most populous, and most frequently served of the Casco Bay islands, and it is a separate, well-covered market on this site in its own right -- including Battery Steele, its shoreline biking and walking routes, and its own ferry-commuter identity into downtown Portland. If Peaks Island specifically is what you are planning around, this site's own Peaks Island page is the better starting point; this page is dedicated to the five other islands.

What This Page Doesn't Cover

This page sticks to what is genuinely documented across Long Island, Chebeague Island, Great Diamond Island, Little Diamond Island, and Cliff Island: Chebeague's golf club and historic clubhouse, its inn, and paddling near Little Chebeague; Great Diamond's Fort McKinley history and Diamond Cove redevelopment; Cliff Island's unpaved, car-free character; Long Island's beaches and secession history; and inter-island ferry travel. Little Diamond Island is not treated as a separate attractions stop here -- it is a tiny, mostly private, seasonal-cottage enclave with no dining or visitor infrastructure independently confirmed, and that thinness is stated honestly rather than embellished. This page does not invent current business hours, admission prices, rental operators, or exact trail distances for any of these islands; confirm time-sensitive details directly with Casco Bay Lines, the Chebeague Transportation Company, or the relevant island organization before you plan a visit around them.