Overlook Mountain was the final of the five Catskills fire tower hikes, one of two that isn't also a Catskills 3500 peak. Because there is also an active tower of some kind on top (radio?), the path up to it is a maintained road, so the trail is wide and smooth - albeit steep.
I was surprised to find the parking lot nearly full on a Thursday afternoon, but the unseasonably warm weather likely had something to do with that. The forecast said there was a small chance of rain later in the evening, and during my hike the sky went from sunny to overcast. Luckily, the clouds were high, so they didn't obscure the views.
The hike itself is pleasant, but the real rewards come at the end. First, there are the remains of an old hotel that burnt down. Then, there is the peak itself with the tower. While the tower was closed, the stairs remain open year-round. From the top landing, I could see 360-degree views of fall colors. There is also a short walk to a viewpoint looking out over the valley.
(There is also an outhouse, so that's a bonus.)
Obviously, this is a hike best done on a clear day; the road hike wouldn't be great for much more than exercise if, say, it was socked in with fog. While by no means easy, it's also a good hike for people who have trouble with uneven footing or depth perception, unlike your typical rocky Catskills hike.
By the way, I read a great deal about the rattlesnakes on Overlook. Well, just like most hikes, it was way overblown. (I always seem to hear alarming things about rattlesnakes on hikes that attract a lot of non-hikers. What are you guys doing out there, practicing your Parseltongue?) These are the rocky ledges all the write-ups describe as snake-infested, but the trail doesn't actually take you up them; this is as close as you get.