Mount Greylock State Reservation

Greylock is the best. First of all, even if you peruse the trail maps online beforehand, I highly recommend stopping at the Visitor Center. The guides are incredibly knowledgeable and can design a hike based on how strenuous and how long you want your hike to be, in addition to what you’d like to see. I can’t get over how well they know the mountain; they know it so well they can tell you which way to walk away from your car in the parking lot (for the compass-​blind among us — where the bleep is north?!) to get to your trail.
Greylock is great too because it has multiple parking lots along the way to the top, so you can plan your starting point accordingly. Also, even though I’m guilty of having a superiority complex over the people who drive up, I do appreciate that you can drive up.
The trails themselves are beautiful, well-​marked, and well-​maintained. The sound of traffic completely falls away during most of the hike. Everyone I’ve met on the hike has been courteous and friendly. All in all, a peaceful and respectful atmosphere.
The view at the top is unbelievable. There is a restaurant/​cafeteria, but there’s also a great hilltop where you can sit, enjoy the view, and scarf down the lunch you packed. And then you can tell your friends you climbed the highest peak in Massachusetts!