Greater Portland and Casco Bay

Greater Portland and Casco Bay covers the southern Maine metro country around Casco Bay, the heart of Maine’s working coast and its largest urban core. The terrain shifts from the working harbor and dense urban peninsula at Portland through the suburban-and-coastal towns north and west, with hundreds of islands scattered across Casco Bay (the Calendar Islands, said to number 365 though the actual count is closer to 200). Cumberland County is the only county in the region. Anchor cities include Portland, South Portland, Westbrook, Scarborough, Cape Elizabeth, Falmouth, Yarmouth, Freeport, Brunswick, and Bridgton (with Shawnee Peak ski area). The Portland Head Light at Cape Elizabeth (the oldest lighthouse in Maine, built in 1791), the Old Port district along the working waterfront, the Portland Museum of Art, and L.L.Bean’s flagship store in Freeport carry most of the visitor weight. Casco Bay’s mailboat ferry to Peaks, Long, and other inhabited islands runs year-round. Most trips here center on Portland. The Old Port and East End neighborhoods carry the food and brewery scene (Portland holds one of the densest restaurant scenes in the country per capita); Freeport runs the L.L.Bean and outlet shopping itinerary; Cape Elizabeth handles the lighthouse-and-rocky-coast circuit; the Casco Bay islands fill day trips by mailboat.

Find your way.

There's no single right route, just the one that fits you.

Casco

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Take the long way.

The best parts of the trip are usually the ones you didn't plan.

Bailey Island

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Take the detour.

The extra miles are often where the story begins.

Cape Elizabeth

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Make time for quiet places.

Not every destination needs noise to be meaningful.

Birch Island

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Stay curious.

A small detour can turn into something worth remembering.

Brunswick

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Start early. Stay late.

The edges of the day tend to hold the best experiences.

Chebeague Island

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Keep it easy.

The best days usually come without pressure or overplanning.

Bustins Island

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The road is the experience.

Getting there is often the point, not just the outcome.

Cape Cottage

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Follow what feels interesting.

Curiosity is usually a better guide than a strict plan.

Bridgton

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