Difficulty: 4 out of 10 (winding, rolling, relatively flat hike)
Fees: **UPDATE April 2018** Cheapskate alert! “To help manage increased visitation to our preserve Teatown charges $5 to non-members for parking. We appreciate our members, who will always park for free.” (Thanks to Jeff Kent for pointing this out in the comments. Five bones well spent.)
This hike is for you if: You’re looking for some nice views, a pleasant stroll, a bit of history and an up-close look at a rich person’s house (without the danger of that rich person calling the cops).
Difficulty: 10 out of 10 (long climb up a big fat mountain with some very steep sections and light rock scrambling toward the top)
Fees: Cheapskate alert! The day-use fee at Woodland Valley Campground (where you’ll park to tackle this hike) is $6 per car as of this writing in 2015, during camping season only (mid-May through mid-October). Money well spent.