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))
Highlights: awesome views, viewing platform, waterfall, wheelchair accessibility
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.

Lion’s Head

Scenery:
Difficulty: 5 out of 10 (short climb, steep in spots)
Highlights: no actual lions, rocky outcropping, sweeping views
Distance: 2.1 miles, Up-and-Back
Approximate roundtrip time: 1.5 Hours
Total ascent: 541 ft
Max elevation: 670 ft above sea level
This hike is for you if: You want to take a short hike to an awesome view. Who doesn’t want to do that?

Little Stony Point

Scenery:
Difficulty: 2 out of 10 (easy little stroll)
Highlights: beach, clifftop views
Distance: 1 miles, Loop
Approximate roundtrip time: 1 Hour
Total ascent: 150 ft
Max elevation: 123 ft above sea level
This hike is for you if: You want a short, easy stroll to a picturesque beach and unique clifftop view of the Hudson River.

Locust Grove

Scenery:
Difficulty: 3 out of 10 (rolling hills)
Highlights: historic estate, some views, woods
Distance: 2.5 miles, Loop
Approximate roundtrip time: 2 Hours
Total ascent: 252 ft
Max elevation: 257 ft above sea level
This hike is for you if: You want to visit a beautiful historic site with some nice sights, manicured grounds and well-maintained trails. Or you’re just a big fan of Morse code.

Millbrook Mountain

Scenery:
Difficulty: 9 out of 10 (long hike with some steep sections)
Fees: Cheapskate alert! There’s a $15 per person fee to hike here. Money well spent.
Highlights: Mohonky goodness, multiple stunning clifftop views
Distance: 7.6 miles, Loop
Approximate roundtrip time: 4.5 Hours
Total ascent: 1,337 ft
Max elevation: 1,631 ft above sea level
This hike is for you if: You want to experience the Mohonk Preserve in all its glory. Mo’ cliffs. Mo’ views. Mohonk. (If you’re a Mohonk brochure writer, PLEASE steal that tagline.)

Minnewaska II: Gertrude’s Nose

Scenery:
Difficulty: 9 out of 10 (long hike with many rocky, rolling climbs)
Fees: Cheapskate alert! The parking fee is $10 per vehicle (as of this writing in April 2015). Money well spent.
Highlights: amazing clifftop views, lake overlooks
Distance: 7.5 miles, Loop
Approximate roundtrip time: 5 Hours
Total ascent: 1,288 ft
Max elevation: 1,804 ft above sea level
This hike is for you if: You enjoy heights, cliffs, awesome views, and walking. Lots and lots of walking.

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).
Highlights: lake, views, waterfall, wheelchair accessibility
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.

Mohonk Mountain House: Labyrinth and Lemon Squeeze

Scenery:
Difficulty: 9 out of 10 (squishing yourself between rocks, ladder climbing, rock scrambling, plus a two-mile-each-way stroll between parking lot and Labryinth)
Fees: 5-alarm cheapskate alert! As of 2022, this hike costs $35 PER HIKER ($30 for kids 4-12 years old)
Highlights: crazy rock labyrinth, great views, rock scrambling, stone tower
Distance: 5.5 miles, Loop
Approximate roundtrip time: 4 Hours
Total ascent: 973 ft
Max elevation: 1,617 ft above sea level
This hike is for you if: You want to see some of the coolest sights in the Hudson Valley and you’re not afraid to crawl under (and around, and through, and over) some rocks to see ‘em.

Monument Mountain

Scenery:
Difficulty: 6 out of 10 (Short-ish climb with some very steep spots)
Fees: Cheapskate alert! It costs $6 to park here (as of this update in 2023, up from $5 previously), payable at an electronic parking meter. Money very well spent.
Highlights: awesome views, clifftop perches, cool rock formations
Distance: 3.5 miles, Loop
Approximate roundtrip time: 2.5 hours
Total ascent: 1,167 ft
Max elevation: 1,613 ft above sea level
This hike is for you if: You want to traverse a steep loop to visit some amazing views and clifftop perches. (Also, you have a deep, abiding respect for gravity, and will be careful along the clifftops.)

Mt. Beacon

Scenery:
Difficulty: 5, 7, or 10 out of 10 (depending on how far you choose to go)
Highlights: clifftop overlook, fire tower, railway ruins
Distance: 4.4 miles, Up-and-Back
Approximate roundtrip time: 1.5 hours (overlook), 3 hours (overlook + fire tower), 5.5 hours (7.7-mile beast loop)
Total ascent: 1,561 ft
Max elevation: 1,653 ft above sea level
This hike is for you if: You want to see some gorgeous views at one of the most popular hiking destinations in the Hudson Valley, and climbing 1,000 vertical feet (or more) to get there is not a deal breaker.

Mt. Tammany

Scenery:
Difficulty: 8 out of 10 (Steep, rocky climb with rocks. And more rocks. Also, rocks.)
Highlights: Delaware Water Gapaliciousness, insane views
Distance: 4.0 miles, Loop
Approximate roundtrip time: 4 hours
Total ascent: 1,639 ft
Max elevation: 1,540 ft above sea level
This hike is for you if: You want to scrabble up a beast of a mountain to see some gorgeous views.