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.

The road is the experience.

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

Bailey Island

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Cities to Explore

Go a little further.

The next turn is often where things start to get interesting.

Casco

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Keep it easy.

The best days usually come without pressure or overplanning.

Cape Elizabeth

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Pause when it feels right.

Some stops aren't on the map, but they're worth taking.

Birch Island

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Go a little further.

The next turn is often where things start to get interesting.

Brunswick

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Let the road decide.

Plans are useful, but flexibility is where the real discoveries happen.

Chebeague Island

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Go a little further.

The next turn is often where things start to get interesting.

Bustins Island

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Stay curious.

A small detour can turn into something worth remembering.

Cape Cottage

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Let it unfold.

Not everything needs to be scheduled to be meaningful.

Bridgton

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