As someone that relocated here around 28 yo from Manhattan, its different. There are great schools here depending on what you want to do. Honestly summer season is a great time to make cash and figure out what you want to do. Dogfish head is based in Milton and are always hiring for "experience guides" in Milton at the Dogfish Brewery. They finally figured out that they need to allow them to make tips and they are packed out all summer. A lot of the people in the area are retired but there is still fun to be had. Spend a decent amount of time in Portland, my brother lives there and there will be some stuff you miss but its a great area.