Massachusetts is named for the park that is now Blue Hills! There's tons of trails with a variety of difficulties, great views of Boston from the tops of Big Blue, Buck Hill, Chickatawbut overlook, and the Quincy Quarries. I'd say the two most iconic hikes here are the red trail up to Elliot tower and the short path around the Quarries trail. If you like difficult hikes, anywhere on the skyline trail is fun.