Can confirm 
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Folks who know: how crowded should I expect Portland to be over Memorial Day weekend? Less so than later in the summer, I know, but should I be thinking about reservations at the places weâre most interested in, expecting the beaches and other touristy spots to be crowded, etc?
I donât think thereâs any time when the answer wouldnât be yes.
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I went up a few days before Memorial Day last year, thinking it would be less crowded. Not reallyâŚit was close enough! Which is why this year I just booked my time right over that week of Memorial Day. I just hope warmer and dry weather holds up. Last year I had fun taking the train up during a Norâeaster.
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Thatâs kind of what I was suspecting/fearing. Well, so it goes, I donât think Iâll have to drive around in the city itself much, and maybe weâll aim day trips north or inland, where we might be headed away from crowds.
Either way, maybe itâll be less crowded than if we were going in late June, which was the original plan. (This trip originated when I realized that the World Cup might make hotels etc prohibitively expensive in Boston or New York around my birthday, so I suggested Portland, but somewhere along the way the plans got moved to Memorial Day weekend.)
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Old Port and central downtown Portland is completely walkable, so I wouldnât even think of bringing a car to the city if I had one. I would leave it parked in the hotel, if you are staying there for any length of time. But the car is great for visiting all the smaller cool towns up and down the coast, and a little bit further off the beaten path.
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