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Where to spend 2 nights between Boston and Kennebunkport

Seattle, Washington
2 posts
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Where to spend 2 nights between Boston and Kennebunkport

Hi there,

I am heading to Maine for a wedding the first weekend of October. However I'm heading out a bit early as it's my boyfriend's birthday on that Friday and I wanted to plan something fun for him. We arrive in Boston on Wednesday evening and have to be up in Kennebunkport for the wedding on Saturday afternoon. My question is, how should I spent Thursday and Friday? We've both spent plenty of time in Boston, so happy to skip that. But which towns would be worth a quick visit in between? Thought maybe spending Friday night in Portland would work out well as I'd heard good things, but what about Thursday?

port republic
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2,412 posts
11 reviews
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1. Re: Where to spend 2 nights between Boston and Kennebunkport

portland is very cool, although it is north of kennebunkport, not between, worth the short extra drive IMHO

If you insist on being between, try Portsmouth

Seattle, Washington
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2. Re: Where to spend 2 nights between Boston and Kennebunkport

Thanks! Would you recommend spending 2 nights in Portland? Or 1 in Portsmouth and 1 in Portland?

Background: we are early 30s, really like trying new restaurants and breweries, and would probably do more wandering than formal tourist activities

Maine
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893 posts
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3. Re: Where to spend 2 nights between Boston and Kennebunkport

I would do both nights in Portland. There are enough restaurants and breweries to keep you busy for many more days than that. If you want to see Portsmouth, you could stop for lunch and a wander around on your way from Boston.

Boston...
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5,586 posts
237 reviews
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4. Re: Where to spend 2 nights between Boston and Kennebunkport

Definitely 2 nights in Portland. My husband and I visited there this summer for 4 nights. I reviewed all the places we ate and the breweries we went to if your interested in my bio.

MA
Destination Expert
for New England
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6,410 posts
201 reviews
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5. Re: Where to spend 2 nights between Boston and Kennebunkport

Definitely Portland. Check out portlandfoodmap.com. I use it to keep up with the fast-moving Portland food scene and to plan eating on our Portland trips.

port republic
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2,412 posts
11 reviews
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6. Re: Where to spend 2 nights between Boston and Kennebunkport

Agree with sox fan, although I don't know why. lunch in portsmouth enroute to portland for both nights.

go yankees

montana
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7. Re: Where to spend 2 nights between Boston and Kennebunkport

We are planning a October trip to the east coast. We are flying to Boston and will spend three nights there then we wish to rent a car and drive to Maine. We will have five nights in Maine and think that we want to spend three of those in Bar Harbor. Looking to break up the drive going and coming back. We like quaint scenic village atmosphere, maybe Kennebuckport one night? Would love suggestions.

Lakewood, New Jersey
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3 posts
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8. Re: Where to spend 2 nights between Boston and Kennebunkport

Where would you spend the night between NJ and Maine? We want to stop before we get into Maine. Maybe Boston but maybe something before that?

Southern Maine
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648 posts
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9. Re: Where to spend 2 nights between Boston and Kennebunkport

While I'm sure you'd enjoy Portland, Portsmouth is very similar and just as much fun. So if you really want some place in between, look at Portsmouth!

10. Re: Where to spend 2 nights between Boston and Kennebunkport

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