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)
Highlights: Hermit Crabs, Magical Beach Walkway
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)
Highlights: Awesome Views, fire tower
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)
Highlights: Cliff Face, Naked People, Waterfall
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)
Highlights: Awesome Views From Several Overlooks
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)
Highlights: Beautiful Lake, NYC Views, Rhododendron Tunnel, Very Nice Overlook
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)
Highlights: Amazing Overlook, Beautiful Lakes, NYC Views, Rhododendron Tunnel
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 during peak periods, Teatown will charge $5 to non-members for parking on weekends and holidays beginning October 1, 2017. 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
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
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.