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Help plan fun and interesting trip from Boston

San Jose, Ca
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55 posts
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Help plan fun and interesting trip from Boston

My Husband and I will be in Boston towards the end of October for a wedding and we are trying to plan a trip from Boston that would be scenic, maybe some history, fun and interesting. We are looking forward to seeing more of the area as we haven't seen any of that part of the country other than Boston. We could either rent a car or take a train. We have between 3 to 5 days for a side trip. Any suggestions would be appreciated.

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Danbury, Connecticut
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1. Re: Help plan fun and interesting trip from Boston

Peggy this post, 10 times, is 9 too many. You should click inappropriate post and let Trip Advisor know so it can delete 9 of them. In fact I will help you with that...

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2. Re: Help plan fun and interesting trip from Boston

I would usually suggest heading north to maine (coast) or New Hampshire (mountains), but I'm pretty sure it will be just past peak foliage season and start to get cold. I'd suggest staying more to the south - Marblehead, Gloucester, and Salem are ocean towns to the north, and then pretty coastal areas to the south are Cape Cod, Martha's Vineyard/Nantucket, and Newport, RI and to the west is the berkshires (mountains/arts). You may want to decide what your interests are and then go from there.

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3. Re: Help plan fun and interesting trip from Boston

I'd maybe rent a car and take a look at the other thread that's currently blooming on coastal drives. The advice there is very good---it's got me wanting to take a trip up the North Shore someday soon! Even in October, that will be beautiful. You can extend the drive up into Maine and spend a night up there.

You'll have the foliage in October, so you might also take a day to go apple picking (I forget when that season ends--someone on here will know).

Apples or not, there will be lovely drives to take out west. You could just tour the western suburbs of Boston (Lexington, Concord, out that way) or go further to the Berkshires. Lots to do out there.

I don't like the train option unless you're sure you know exactly where you want to go and the train goes there. Cars give you more options. The flip side is that the train is enjoyable by everyone but... In Oct, you might have chilly weather or cold rain and on such a day, it's nice to have a car to retreat to.

Boston, MA
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4. Re: Help plan fun and interesting trip from Boston

When in October ... tourism to the white mountains usually peaks Columbus Day weekend (oct 8 this year) and the weekend after that is still pretty nice ... it might be cold, be the leaves will be nice.

The coastal trip is also an idea.

Don't rule out Cape Cod ... it may not be 'beach weather' but there's still lots going on .

5. Re: Help plan fun and interesting trip from Boston

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