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Massachusetts/Connecticut road trip planning

Hi folks

I'm heading over to Boston in July - arriving at the airport late Sat night, departing a week later. I've been to Boston quite a few times so keen to see more of the surrounding areas. I'll probably head into downtown Boston on the Sunday for lunch though (I enjoy walking round the Back Bay area and my understanding is it's free parking on a Sunday too?), however looking for suggestions for the rest of the trip.

I've been to Providence and Martha's Vineyard before so this time I was thinking of heading West to see more of MA and drop down into CT too.

At present I was thinking of heading out past Leominster, across to Greenfield, down to Springfield then Hartford before heading back up via Worcester but very much open to ideas. Keen to know of some nice places to visit, just looking for a nice relaxing trip - open to suggestions really!

Thanks in advance.

https://preview.redd.it/qaij9nwayp5f1.png?width=1315&format=png&auto=webp&s=95e95e6e589b77da85c44bde70082fb194cd6e0e



#activities #travel
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