If you come out here around this time of year you could go to the Big E (eastern states expedition). Which is a big fair for all of the new england states.
Boston is a great city to be in. Its a fair amount more peaceful and safer than New York. The North End in Boston is known as Little Italy and they have some outstanding Italian food. The original Pizzeria Regina is located there and it is probably the most delicious Pizza you've ever had. If you dont want to be in the city go to the east coast. Cape Cod has some beautiful beaches. If you're up for a ferry ride the island of Nantucket is quite elegant and a great place to walk around and relax. Its what I call the playground of the rich and famous though. Or you can enjoy the north shore where I live haha. Salem is the original witch city, they have some cool meuseums and is probably the best place to be during Halloween in the whole northshore.
Boston. Nuff said. It's my favorite city. I've been a Red Sox fan since I was ten years old and finally had my chance to visit the town and Fenway Park in 2000. It rained the whole weekend, all the games were cancelled, and I fell in love with the town. Been back several times since and can't wait to go back. There's more history in that town than there is in some countries. Take a good guide book but try not to be a total tourist. Seek out the local joints. That's where you'll get a feel for the city.
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