Kaaterskill Falls II (upper trailhead)

Scenery:
Difficulty: 5 out of 10 (2 out of 10 for an easy stroll to the viewing platform, 5 out of 10 if you also visit the lower falls, 7 out of 10 for a rugged hike if you follow all the steps below (to lower falls and Inspiration Point))
Distance: 4.7 miles
Approximate roundtrip time: 3.5 Hours
Total ascent: 1,177 ft
Max elevation: 2,211 ft above sea level
This hike is for you if: You want to check out a mind-blowing two-tier waterfall, ogle some amazing views, and explore some awesome trail features.

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.

Croton Gorge Park

Scenery:
Difficulty: 3 out of 10 (short climb up a dirt road)
Fees: Cheapskate alert! Access to the park is $10 per car ($5 if you have a park pass), May through Labor Day only. All other times, it’s free.
Distance: 2.1 miles, Up-and-Back
Approximate roundtrip time: 1.5 hours (includes playground stop – WHEEEE!)
Total ascent: 188 ft
Max elevation: 254 ft above sea level
This hike is for you if: You want to take a relatively easy stroll up to, around, and over a giant honking waterfall.

Minnewaska State Park Preserve

Scenery:
Difficulty: 6 out of 10 (longish hike with hilly sections)
Fees: Cheapskate alert! The parking fee is $10 per vehicle (as of April 2015).
Distance: 6.4 miles, Loop
Approximate roundtrip time: 4 Hours
Total ascent: 814 ft
Max elevation: 1,908 ft above sea level
This hike is for you if: You want to pack enough highlights for four hikes into one four-hour loop. And also, you’re not afraid of some crowds.

Walkway Over the Hudson

Scenery:
Difficulty: 2 out of 10 (flat, paved stroll)
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.