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.

Leave room for the unexpected.

The best parts of a trip rarely show up on an itinerary.

Bustins Island

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Cities to Explore

Stop when something catches your eye.

Those moments tend to matter more than the planned ones.

Brunswick

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Not every place needs a reason.

Sometimes it's enough just to be there.

Chebeague Island

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Let the road decide.

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

Cape Cottage

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Let it unfold.

Not everything needs to be scheduled to be meaningful.

Bridgton

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Take the detour.

The extra miles are often where the story begins.

Bailey Island

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Follow what feels interesting.

Curiosity is usually a better guide than a strict plan.

Casco

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More road, less rush.

There's no need to hurry through something worth experiencing.

Cape Elizabeth

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Start early. Stay late.

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

Birch Island

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