Go down to Exchange St in Portland where the local longboard freaks hangout. They will take you places, magical places, like the western prom!
I would look outside the city, but it's not that hilly around the outside of portland. I live in Sanford and it seems the closer you get to the NH boarder the better the hills. Good luck, and maybe you will see me in Portland flying around the streets. I'll take you places, like the western prom...
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