Teatown Lake Reservation

Scenery:
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.)
Highlights: beautiful trails, floating bridge, lakes
Distance: 4.2 miles, Loop
Approximate roundtrip time: 2.5 Hours
Total ascent: 542 ft
Max elevation: 606 ft above sea level
This hike is for you if: You want to take a pleasant stroll in a beautiful preserve with interesting things to see all around. Also, you have a thing for lily pads.

Tremper Mountain

Scenery:
Difficulty: 8 out of 10 (long slog up a big fat mountain)
Highlights: beautiful trail, Catskill views, fire tower, lean-to shelters
Distance: 6.5 miles, Up-and-Back
Approximate roundtrip time: 4 Hours
Total ascent: 2,192 ft
Max elevation: 2,766 ft above sea level
This hike is for you if: You want to huff and puff up a mountain to see some righteous views from one of the five Catskill fire towers.

Undercliff/ Overcliff

Scenery:
Difficulty: 5 out of 10 (relatively flat, easy, long-ish stroll)
Fees: Cheapskate alert! There’s a $15 per person fee to hike here. Money well spent.
Highlights: cliffs, rock climbers, views
Distance: 5 miles, Loop
Approximate roundtrip time: 2.5 Hours
Total ascent: ft
Max elevation: ft above sea level
This hike is for you if: You like to watch crazy people climbing sheer cliffs while you’re strolling along carriage roads with huge views.

Vanderbilt Mansion

Scenery:
Difficulty: 4 out of 10 (Pleasant stroll with some hilly sections)
Highlights: big ol’ house, views, waterfall, wheelchair accessibility
Distance: 3 miles, Loop
Approximate roundtrip time: 1.5 Hours
Total ascent: ft
Max elevation: ft above sea level
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).

Walkway Over the Hudson

Scenery:
Difficulty: 2 out of 10 (flat, paved stroll)
Highlights: awesome views, people watching, wheelchair accessibility
Distance: 3 miles, Up-and-Back
Approximate roundtrip time: 1.5 Hours
Total ascent: 88 ft
Max elevation: 306 ft above sea level
This hike is for you if: You’re looking for beautiful views and a unique stroll on the longest raised pedestrian walkway in the whole (entire freaking!) world.

Wittenberg Mountain

Scenery:
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.
Highlights: amazing views at the top, beautiful trails, light rock scrambling
Distance: 7.2 miles, Up-and-Back
Approximate roundtrip time: 6 Hours
Total ascent: 2,645 ft
Max elevation: 3,780 ft above sea level
This hike is for you if: You want to see one of the best views in the Catskills, and you’re prepared to climb a big fat honking mountain to see it.