Red Hill fire tower

Scenery:
Difficulty: 5 out of 10 (hilly stroll with some steep-ish stretches)
Highlights: fire tower, great views, totally sweet outhouse, wonderful Catskill vibe
Distance: 2.8 miles, Up-and-Back
Approximate roundtrip time: 2.5 hours
Total ascent: 837 ft
Max elevation: 3,057 ft above sea level
This hike is for you if: You want to take a relatively short stroll to a fire tower with a gorgeous view of the Catskills. Also, you appreciate attention to detail in your outhouses.

Red Mountain

Scenery:
Difficulty: 4 out of 10 (relatively easy stroll with some hill climbs and grassy stretches)
Highlights: cows, giant old trees that might be ents, meadows, that new preserve smell, wonderful views
Distance: 2.7 miles, Loop
Approximate roundtrip time: 1.5 hours
Total ascent: 574 ft
Max elevation: 1,223 ft above sea level
This hike is for you if: You want to take a pleasant stroll on some great new trails, see some crazy big trees, and scope out some beautiful views across picturesque meadows. (This place really chews through the adjectives.)

Red Wing Recreation Area

Scenery:
Difficulty: 4 out of 10 (short hike up a medium-sized hill with steep sections)
Highlights: pleasant trails, quick hike, scenic overlook
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.
Highlights: Ice Caves, lake, Verkeerderkill Falls, views
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)
Highlights: megaliths, varied terrain, views
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.

Shaupeneak Ridge

Scenery:
Difficulty: 4 out of 10
Highlights: beautiful woods, lake that belongs In Maine, views
Distance: 2.2 miles, Loop
Approximate roundtrip time: 1.5 Hours
Total ascent: ft
Max elevation: ft above sea level
This hike is for you if: You want a great hike with views and a lake, but you’re not looking for much in the way of elevation change (though you could climb a steep ridge if you’re so inclined — there are two parking lots for this hike, so the degree of difficulty depends on where you park. We’re parking in the wimpy upper lot today, but feel free to tackle this hike from the burly lower lot.)

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, wheelchair accessibility
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.