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I get out to W. Boylston for my job periodically....can't wait for the next time, I'll be on my new bike! Quabbin and Wachusett are beautiful areas for riding.....If you ever need some good suggestions for Cape Cod or Islands destinations, let me know...
I learned to ride on those roads around Worcester!! In fact I took the safety course in WeBo across from the movie theater. Just go, and you'll be happy. Not much on the cape tho, unless you find a nice weekend with no traffic!!
Hey Benny- now's the time to hit the Cape and Islands....the tourists have left, the weather is still beautiful, off season prices on accomodations, some amazing seaside riding, always a blast to ferry over to Martha's Vineyard and......and .....LOBSTAH DINNAHS!!! 
"Let your soul shine,
It's better than sunshine,
It's better than moonshine,
****** sure better than rain."
-ABB
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