Fire Tower in Grafton
I've been there at all seasons and it's always a great view of the surrounding forests, including Grafton Lakes State Park.
You get to it by taking a left onto Babcock Lake Road (when coming from the west) - the road is after the old Grafton Elementary School. Then, follow that for a couple miles until you come to a road on the left called Fire Tower Road.
You'll pass a lot of cool and sometimes rustic houses (and wonder how they survive the winters there), and you'll see a dirt road going up a steep-ish looking hill on the left. Park at the bottom and walk up (it's just a quick hike) then you can climb the fire tower.
Obviously, if you get to the end of the road you've gone too far but you can - if you want - take a hike into the state park from there. One of these years I want to snowshoe from the park up to the fire tower.
My colleague just wrote about the tower in today's paper: http://www.troyrecord.com/articles/2012/06/26/news/doc4fe8ecb41d5b3054306326.txt
Also of interest in Grafton: The Berkshire Bird Paradise Sanctuary and Grafton Peace Pagoda
(surprisingly, or maybe not so surprisingly, there's actually a lot to do out there - but watch out for the ongoing road work!)