Stache excellent thread. I also like Giant Ledge and Overlook Mountain fire tower hikes.
I like North/South Lake Hike up to North point. You can see it here and other hikes on Catskill Center Virtual Hikes.
http://www.catskillcenter.org/vhikes/hikes.html
The escarpment trail from North Lake is also a nice trail for folks that want a flat trail with awesome views.
I also like hiking to Hunter Mountain fire tower from the Spruceton Side. Driving up the Spuceton valley from Route 42 is like going back in time. In over 50 years there are very few visual changes. The trail up to Hunter Fire Tower is a nice even grade with only one steep spot for about a half mile. No rambling over rocks required. There is an excelent view where John Robb's leanto use to be. Sad they removed the leanto which has been there since the 1960s. There is even a second trail down to the Spruceton trail head parking lot so you don't need to hike the same trail up and down.
For more information on Hunter Fire Tower and other fire tower hike see:
http://www.catskillcenter.org/towers/ 
The beautiful Spuceton Valley as seen from the John Robb Lean-to
For some rambling over, up, and under not for the faint of heart try the Lemon Sqeeze trail at Mohonk Mountain outside of New Paltz. If it turns out that the ramble is too much for you, there are places where you can bail out and hike up a carriage trail. At the end of the ramble its straight up a narrow couloir using wooden ladders. They don't call it the lemon squeeze for nothing. The Mohonk Mountain house has an excellent lunch that is a little pricey but includes the price of the grounds and parking, which makes it a good choice. My department from work has done the lemon Squeeze and lunch at Mohonk now tow years in a row. Makes for excellent team building exercise.
http://www.mohonk.com/ 