Red Wing Recreation Area

Scenery:
Difficulty: 4 out of 10 (short hike up a medium-sized hill with steep sections)
Distance: 2 miles, Loop
Approximate roundtrip time: 1.5 Hours
Total ascent: 619 ft
Max elevation: 729 ft above sea level
This hike is for you if: You’re looking for a short hike to a surprisingly nice payoff, all within view of the pizza place where you may decide to stuff your gullet later.

Sam’s Point

Scenery:
Difficulty: 6 out of 10 (but you could make it a 9 if you tried to do everything)
Fees: Cheapskate alert! The parking fee is $10.00. After hiking here, I hope you’ll agree that 10 bones is a steal. UPDATE April 2022: This May, Sam's Point is introducing an online reservation parking system for weekends and holidays, May-October. You MUST reserve to park here! See the "Directions" section below for more details.
Distance: 5 miles, Up-and-Back
Approximate roundtrip time: 3 Hours
Total ascent: 0 ft
Max elevation: 0 ft above sea level
This hike is for you if: You want to visit what very well might be the coolest natural place in the Hudson Valley.

Schunemunk Mountain

Scenery:
Difficulty: 9 out of 10 (long hike up and down a big fat mountain)
Distance: 6.4 miles, Loop
Approximate roundtrip time: 4 Hours
Total ascent: 1,723 ft
Max elevation: 1,658 ft above sea level
This hike is for you if: You want to climb a big ol’ mountain to sit on some huge rocks with awesome views.

Silver Sands State Park

Scenery:
Difficulty: 3 out of 10 (flat, sandy, rocky stroll with the potential for going the full Gilligan and getting stranded on a desert isle)
Distance: 2.6 miles, Partial Loop
Approximate roundtrip time: 2 hours (or 4 hours, if you bring my kids)
Total ascent: 127 ft
Max elevation: 45 ft above sea level
This hike is for you if: You want to walk on a magical highway of shells and rocks to an island just off the coast of Connecticut.

Stissing Mountain

Scenery:
Difficulty: 6 out of 10 (steep, relatively short climb)
Distance: 1.9 miles, Partial Loop
Approximate roundtrip time: 2 - 3 Hours
Total ascent: 926 ft
Max elevation: 1,415 ft above sea level
This hike is for you if: You’re looking for a steep climb to a big payoff. And also, you think it sounds like fun to climb a swaying, 90-ft structure in the middle of the woods.

Stony Kill Falls

Scenery:
Difficulty: 4 out of 10 (easy stroll with some clambering at the falls)
Distance: 1.45 miles, Up-and-Back
Approximate roundtrip time: 1.5 Hours
Total ascent: 193 ft
Max elevation: 1,291 ft above sea level
This hike is for you if: You want to take a short, pleasant stroll to a breathtaking 90-ft waterfall.

Storm King Mountain

Scenery:
Difficulty: 6 out of 10 (moderate hike with a few very steep, rocky sections)
Distance: 2.5 miles, Loop
Approximate roundtrip time: 2.5 Hours
Total ascent: 893 ft
Max elevation: 1,385 ft above sea level
This hike is for you if: You want some steep, quick climbs to some of the best views of the Hudson Valley you’re likely to find without renting a helicopter.

Surprise Lake (via Bearfort Ridge)

Scenery:
Difficulty: 7 out of 10 (long hike over very rocky terrain with a few steep sections)
Distance: 6.0 miles, Loop
Approximate roundtrip time: 4 - 5 Hours
Total ascent: 1,240 ft
Max elevation: 1,418 ft above sea level
This hike is for you if: You don’t mind stepping on a few (thousand) rocks to see some gorgeous woods, nice views and a beautiful, tucked-away lake.

Surprise Lake II (via Greenwood Lake overlook)

Scenery:
Difficulty: 9 out of 10 (steep climbs & descents, rough terrain, rock scrambling)
Distance: 4 miles, Loop
Approximate roundtrip time: 3.5 Hours
Total ascent: 1,191 ft
Max elevation: 1,424 ft above sea level
This hike is for you if: You want to take a memorable hike with views, lakes, a rhododendron tunnel, small rock scrambles and a general awesome vibe. Oh, and you enjoy burning lots of calories.

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.)
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)
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.