Photograph by virsuziglis, Getty Images
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The historic Portland Head Light, built in 1791, is one of the oldest lighthouses in the United States still in operation.

Photograph by virsuziglis, Getty Images

Everything to Know About Portland, Maine

Here's how to plan the best possible trip to this charming seaport.

In recent years, young, creative, progressive people have made the trek to the Portland peninsula and its surrounding communities, joining generations of Mainers in laying down roots in the quiet seaside city. Together, the two groups balance a history of winter-hardened New England self-sufficiency with a taste of the contemporary, creating a vibrant urban scene alongside a historic working waterfront.

When to Go

It’s hard to beat the mild Maine summers, but the late fall shoulder season is when most Portlanders take back the city after the tourist crowds subside.


Thousands of runners flock to neighboring Cape Elizabeth each August for the scenic Beach to Beacon 10K, while food enthusiasts look forward to the city’s annual Harvest on the Harbor each fall.

What to Eat

Maine and lobster go hand in hand, and luckily there’s no shortage of ways to enjoy this succulent treat. Steamed, grilled, in chowder, or on a roll, lobster is by far Maine’s most delicious export.

Souvenir to Take Home

It’s hard to miss the recycled sail bags from Sea Bags hanging in shop windows throughout town, and the quirky designs of the Imagine Maine branded tees and sweatshirts are a cozy reminder of any trip to Maine, but the L.L. Bean Duck Boot is by far the most iconic of Maine-made goods.

Sustainable Travel Tip

Bring your bike and board one of the Casco Bay Lines ferries to tour one of the larger islands like Peaks, Great Diamond, or Chebeague for a quiet day of exploration away from the city.

Instagram-Worthy View

The panoramic views from the top of the Portland Observatory, the country’s last surviving maritime signal tower, are photo-worthy at any time of the day.