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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, Up-and-Back
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: Cornish 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.

Beebe Hill Fire Tower

Scenery:
Difficulty: 4 out of 10 (short, moderate climb)
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.

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.)
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.

Lion’s Head

Scenery:
Difficulty: 5 out of 10 (short climb, steep in spots)
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?

Indian Ladder Trail

Scenery:
Difficulty: 3 out of 10 (relatively flat, easy stroll with a large staircase on either end)
Fees: Cheapskate alert! There's a new (as of 2018) parking fee here of $6. Money well-spent.
Distance: 2.5 miles, Loop
Approximate roundtrip time: 2.5 Hours
Total ascent: 541 ft
Max elevation: 1,207 ft above sea level
This hike is for you if: You want to take a relatively easy hike with a massive payoff, and you’re not scared to drive to Albany to make it happen. Also, you’re cool when your nature comes served with crowds.

Bear Hill Preserve

Scenery:
Difficulty: 3 out of 10 (flat, easy stroll with optional rock-clambering)
Fees: Cheapskate alert! The price to hike here keeps going up (from three dollars in 2015). There’s now a seven-dollar (per hiker) day-use fee here (peak times only – other times, it’s free!), with no charge for hikers under 12. You can also get an annual pass for twenty-five bones. Money very well spent.
Distance: 1.5 miles, Up-and-Back
Approximate roundtrip time: 2 Hours
Total ascent: 187 ft
Max elevation: 1,931 ft above sea level
This hike is for you if: You want to take an easy stroll to some awesome clifftop views with fun rock formations to explore.