59 days in Portland Itinerary

59 days in Portland Itinerary

Created using Inspirock Portland trip planner

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Portland
— 58 nights

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58
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Portland

The Forest City

Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
Eschew the tourist crowds and head to Allagash Brewing Company and Fishing Charters & Tours. Explore Portland's surroundings by going to Bailey Island (Giant's Stairs Trail & Bailey Island Bridge), Boothbay Harbor (Cabbage Island, Boothbay Region Land Trust, &more) and Kennebunkport (Walker's Point, St. Ann's Episcopal Church, &more). There's lots more to do: make a trip to Commercial Street, step off the mainland to explore Casco Bay Islands, grab your bike and head to Eastern Promenade Trail, and take in the waterfront activity at DiMillo's Old Port Marina.

For other places to visit, reviews, more things to do, and other tourist information, read Portland travel tool.

In September, daytime highs in Portland are 73°F, while nighttime lows are 52°F. Finish your sightseeing early on the 29th (Thu) so you can travel back home.

Things to do in Portland

Parks · Museums · Nature · Outdoors

Side Trips