Sarah M.
Yelp
We pulled up to the information center and I was taken aback by it being a picturesque house upon a hill, sitting behind what was once, probably, a carriage house. It's the nicest info center I have ever seen, and probably DCR's way of saying: this is nature and stuff, but it's also Milton, dammit.
Parking is plentiful but could be tricky on a nice day. Try the parking lot across the street from the main entrance first, but if that's full, there is a big lot by Houghton's Pond about a half-mile away. You can walk to trailheads from there.
Hiking-wise, I can only speak for the 3-mile Skyline Loop, but it was a well-maintained trail that was way better marked than the Fells trails are. The first portion of the northern branch is STEEP! Like, bouldering in the White Mountains steep. My legs felt a little jelly-ish and I had to stop before continuing. Fortunately, after that, things level off, and though there a few more steep sections, most of them are actually downhill. The tower, your reward at the end, is beautiful itself and affords great views of the hills and ponds to the south and, of course, Boston to the North. You can even see the ocean and harbor islands from here, which is cool! The south loop is more level, and in total it took our group a quick 2 hours to complete the whole thing.
All in all: it isn't a hike in New Hampshire, Maine, or Vermont. But it's less than an hour from my front door and is hella better cardio than watching more Frasier. Yeah, it'll do.
Houghton's Pond, by the way, looks beautiful. It has a small beach I'd love to check out in the summertime.