Does anyone have any hikes up hills or mountains near the city they can recommend?
Most of my hiking and camping experience in New England has been in the White Mountains, and the closest mountain hike i've done is Monadnock. I know nothing's really comparable down here with the Whites, but sometimes smaller features can be surprising.
I see Wachusett out there on the map, but I've heard mixed anecdotal reviews on hiking it.
Things I like: views, forests, fun rock scramble bits.
How far is "near Boston"? If you haven't yet discoverd the Middlesex Fells Reservation which is just a few miles there are some areas there that are great. The Wapak trail is a great hiking trail that covers a bunch of summits in Northern MA/southern NH. Mt Wachusett area can be a great hike - there are a number of connecting trails/routes that can take you away from potential crowds and offer views that are worth the trip. The route 2 corridor offers a number of small hikes that offer great views of the area as well