For simple, relatively easy and quick hikes directly around Wolfeboro, the formentioned Lakes Region Conservation Trust and their Knight's Pond Property are worth a look. It's located off the Winnpesaukee Estates Development (as you're taking Rte 28 into Wolfeboro, it's on your right just after you cross the Alton/Wolfeboro town line).
Granted I might be a bit biased towards Knight's Pond as my grandfather before he passed away almost 2 years ago was on the Board of Directors of the Lake's Region Conservation Trust and was a major donor for the funds that the LRCT used to acquire the Knight's Pond Property
