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.)

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.

Bear Mountain State Park

Scenery:
Difficulty: 8 out of 10 (rugged climb with some steep rock-clambering)
Fees: Cheapskate alert! The parking fee here is $10 per vehicle. Money well spent.
Highlights: awesome views, cool trails, stone tower, vending machines
Distance: 4.5 miles, Loop
Approximate roundtrip time: 3.5 Hours
Total ascent: 1,208 ft
Max elevation: 1,319 ft above sea level
This hike is for you if: You want to tackle a beautiful, steep climb to one of the most wide-open panoramic views in the Hudson Valley. Also, you can ignore the fact that you could have just driven to the top.

Beebe Hill fire tower

Scenery:
Difficulty: 4 out of 10 (short, moderate climb)
Highlights: awesome views, fire tower
Distance: 2.0 miles, Up-and-Back
Approximate roundtrip time: 1.5 hours (or 3 hours, if you bring my kids)
Total ascent: 485 ft
Max elevation: 1,822 ft above sea level
This hike is for you if: You want to climb a small(ish) hill to a fire tower with some seriously sweet views.

Giant Ledge and Panther Mountain

Scenery:
Difficulty: 6 out of 10 (or 9 out of 10 if you choose to climb Panther Mt., too)
Highlights: awesome views, very large (giant even!) ledges
Distance: 3.2 miles, Up-and-Back
Approximate roundtrip time: 2 Hours (or 4 hours if you hit Panther Mt., too)
Total ascent: 1,090 ft
Max elevation: 3,170 ft above sea level
This hike is for you if: You want to stand on some awesome ledges with amazing Catskill views. Also, you don’t mind having some company on the trail.

Walkway Over the Hudson

Scenery:
Difficulty: 2 out of 10 (flat, paved stroll)
Highlights: awesome views, people watching, wheelchair accessibility
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.

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.