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Monument Mountain

Scenery:
Difficulty: 6 out of 10 (Short-ish climb with some very steep spots)
Fees: Cheapskate alert! It costs $5 to park here (as of this writing in 2020), payable at an electronic parking meter. Money very well spent.
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. Tammany

Scenery:
Difficulty: 8 out of 10 (Steep, rocky climb with rocks. And more rocks. Also, rocks.)
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.

Tremper Mountain

Scenery:
Difficulty: 8 out of 10 (long slog up a big fat mountain)
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.

Great Swamp

Scenery:
Difficulty: 5 out of 10 (flat stroll leading to hilly stretches)
Distance: 4.9 miles, Up-and-Back
Approximate roundtrip time: 3 hours
Total ascent: 817 ft
Max elevation: 765 ft above sea level
This hike is for you if: You want to stroll on a beautiful boardwalk that passes over peaceful marshlands on the Appalachian Trail, then check out the biggest honking oak tree for about 1,000 miles in either direction.

Red Hill fire tower

Scenery:
Difficulty: 5 out of 10 (hilly stroll with some steep-ish stretches)
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.

High Banks Preserve

Scenery:
Difficulty: 3 out of 10 (friendly stroll with gentle inclines)
Distance: 3.1 miles, Loop
Approximate roundtrip time: 1.5 hours
Total ascent: 370 ft
Max elevation: 294 ft above sea level
This hike is for you if: You want to take a nice stroll in the woods around a new, well-maintained preserve with varied terrain and interesting trails.

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.

Race Mountain (Mount Race)

Scenery:
Difficulty: 8 out of 10 (rugged climb with some stream-hopping and steep sections)
Distance: 7.1 miles, Up-and-Back
Approximate roundtrip time: 5 Hours
Total ascent: 2,080 ft
Max elevation: 2,360 ft above sea level
This hike is for you if: You want to traverse some of the most beautiful trails in the area, see some pretty waterfalls, and check out a nice view at the top.

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.
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.

Bull Hill (Mt. Taurus) II: Full Loop

Scenery:
Difficulty: 9 out of 10 (long, steep haul over a big fat mountain)
Distance: 5.9 miles, Loop
Approximate roundtrip time: 4.5 Hours
Total ascent: 1,522 ft
Max elevation: 1,421 ft above sea level
This hike is for you if: You’re looking for a hard climb with several great views along the way. Also, you want to visit some ruins that will make you feel better about all the home improvement projects you’ve been putting off.

Hunter Mountain

Scenery:
Difficulty: 9 out of 10 (steep, rocky, long-ish climb up a big fat mountain)
Distance: 5.0 miles, Partial Loop
Approximate roundtrip time: 4.5 Hours
Total ascent: 2,217 ft
Max elevation: 4,071 ft above sea level
This hike is for you if: You want to haul yourself up the second-highest peak in the Catskills to see some amazing views.

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.