Following a morning walk through Central Park on Sunday, I took a train back to Connecticut and drove up to Meriden's Hubbard Park.
The trail up was a bit disappointing at first. It was very flat and ran along a highway, but then you hit this footbridge that brings you over the highway and closer towards the ridge and it gets much more interesting. You cross a wooden bridge, pass a natural spring, and then the trial gets very steep, very fast.
The view from the top is one of the best I've seen in Connecticut. There's a plaque there that claims the tower has the distinction of being the highest point within 25 miles of the coast between Florida and Maine, but I've read that this isn't true. Still, it's an amazing view. You can see Sleeping Giant State Park, New Haven, and the outline of Long Island far off in the distance. If you're not a hiker but still want to check it out, there's a road that will take you straight to the tower.
I've posted more info about Castle Craig and Hubbel Park including additional photos and a trail map here.