So, I’ll be the first to admit I haven’t hiked every single trail in the Hudson Valley and Catskills (I mean, there’s hundreds), but I have hiked MOST of them, writing about the best.

The list below includes hikes from six counties, and all four mountain formations in the region – the Catskills, the Shawangunks, the Taconics, and the Hudson Highlands. Each of the ten entries link to the full article, with additional pictures, videos, and hijinx. The map is interactive, with the trailheads of each hike marked.

Enjoy the best hikes in the Hudson Valley and Catskills, and, most importantly, leave nature as you found it. We are all guests.

 

#10 – Shaft 2a

Trailhead Location – Kerhonkson, Ulster County

Length – 1.5 Miles

Difficulty – Easy-Moderate

Traffic – Medium-Heavy

Trail Directions – An in-and-out from the new DEC parking lot.

 

Once a well-kept secret, The Chillest Spot in Ulster County is now a a well-known secret, and the Department of Environmental Conservation (DEC) had to blaze an official trail in 2018 to stop erosion and habitat loss from zealous hikers climbing the ravine up to the falls.

The trail begins in a giant basin and passes by a seemingly random helicopter pad (actually owned by the NYC Department of Environmental Protection as part of their reservoir system) before entering the forest. The trail switchbacks up a ravine to the top of a 120-foot waterfall with a series of swimming holes.

The spot was once (unofficially) clothing-optional, and it wasn’t uncommon to see couples sunning half- of fully-naked. With the trail now christened by the DEC, there’s a lot of children about, so I would probably keep it in your pants (or bikini bottoms).

 

#9 – High Falls

Trailhead Location – Philmont, Columbia County

Length – 1.3 Miles

Difficulty – Easy

Traffic – Moderate

Trail Directions – Take the Green Trail .2 miles to the Upper Blue Trail, which leads to the Agawamuck Creek – don’t stop at the first falls – High Falls itself is a few hundred feet upstream. Turn back and continue on the Green Trail to get to the falls’ precipice, then take the Red Trail back to the parking lot.

The easiest hike on the list, as well as the hardest to get lost on, the High Falls Conservation Area boasts a 150-foot waterfall plunging into a deep pool. Though shorter than the much-lauded Kaaterskill Falls, High Falls clearly has a higher flow rate, and is also not horrible. Just – don’t go to Kaaterskill Falls. Go here.

 

#8 – Balsam Mountain

Trailhead Location – Arkville, Delaware County

Length – 5.1 miles

Difficulty – Moderate-Difficult

Traffic – Light

Trail Directions – A hard-to-confuse lollipop trail from the DEC parking lot on Rider Hollow Road. Take the trail .3 miles to where it splits, then take a left. There are two other junctions on the trail – go right on each one.

At 3,623 feet, Balsam Mountain is one of the 35 Catskill Peaks over 3,500 feet – and one of the easiest, if you just want to claim to have done one. Towards the top, you’re greeted with beautiful conifer forest. The best view is about .1 miles before the mountain’s acme.

 

#7 – Brace Mountain

Trailhead Location – Millerton, Dutchess County

Length – 3.6 miles

Difficulty – Hard

Traffic – Nearly Empty

Trail Directions – Easy out-and-back – though the location of the trailhead is somewhat disconcerting.

The trail begins in what looks like the yard of a very out-of-place apartment building, then enters the forest and shoots up a surprisingly steep ridge before leveling into an easier hike.

Brace Mountain is the highest point of the ridge, and is broad and bare of tall vegetation, so the views are spectacular – you can see the Catskill High Peaks 50 miles to the west, and the Berkshires Mountains in Massachusetts to the east. South Brace Mountain, which the trail meets before leading to Brace Mountain, has great views of Riga Lake in Connecticut.

Best of all, some maniac has erected a giant Gadsen Flag at Brace Mountain’s peak that has been romantically tattered by the gusty winds. It makes you want to tear up. Not because of the wind. Because of freedom.

 

#6 – Blackhead & Black Dome

Trailhead Location – Maplecrest, Greene County

Length – 6.1 miles

Difficulty – Very Hard

Traffic – Light

Trail Directions – From the lot at the end of Big Hollow Road, take the red trail. The route is a giant lollipop, but take a detour on the Escarpment Trail at the top of Balckhead for some amazing views, and then another detour where the yellow and red trails juncture to get to the top of Black Dome.

A thigh-busting hike to the third- and fourth-highest peaks in the Catskills, this route brings you to seven distinct overlooks, so you’re able to see in each direction at some point in the hike. My personal favorite is a 250-foot cliff with a vista of the Greene County lowlands and Albany County. The main outlooks on Blackhead and Black Dome are visible from each other, so you can attempt to communicate with hikers on the opposite mountain through signal flags or…I dunno, a shofar.

Not for the weak of heart.

 

#5 – Overlook Mountain

Trailhead Location – Woodstock, Ulster County

Length – 4.6 miles

Difficulty – Moderate

Traffic – Heavy

Trail Directions – An easy in-and-out off Meads Mountain Road

Mid-way through the trudge up this dull, often busy forest road, you might stop, glare behind you and mutter, “Why the fuck did the Other Hudson Valley guy recommend this? This absolutely sucks.”

…and the first two-thirds of it does. However, once the forest road thins to a trail, you’re greeted by dual wonders: the ruins of the Overlook Hotel and a fire tower. The hotel has been abandoned since 1923, after it burnt down a second time (Catskill resorts had a habit of doing this), but the rock structure remains, and you can clamber over the worn walls and staircases.

The fire tower, about a third of a mile from the ruins, gives you a 360-degree view, so you can take in both the Hudson Valley and Indian Head Wilderness with a turn of the head.

 

#4 – Millbrook Ridge to Gertrude’s Nose

Trailhead Location – Gardiner, Ulster County

Length – 10.5 miles

Difficulty – Hard

Traffic – Moderate-Heavy at first, then Moderate-Light after Millbrook Mountain.

Trail Directions – From the Trapps Parking Lot (on Mohonk Preserve property, so you’ll have to pay), take the Millbrook Ridge Trail, which leads to Gertrude’s Nose Trail at Millbrook Mountain. Follow it to Gertrude’s nose. Turn around. When passing Millbrook Mountain on the way back, take the Coxing/Trapps Trail back to the lot.

The trail begins at the Trapps, which helps make the Shawangunk Ridge one of the most popular rock-climbing spots in the country – take a jaunt down Undercliff Carriage Road if you want to watch (refrain from agonized screams of “HE’S GONNA DIE!”).

After the first half-mile on the Millbrook Ridge Trail, the path slackens to a low grade, running along the spine of the ridge. The ridge’s eastern face is so steep, craning your neck over its edge feels like looking out of a plane’s window, a group of buildings on Route 44/55 squatting 400 feet straight below you.

This is the longest hike on the list, but push yourself to get to Gertrude’s Nose – it’s worth it.

 

#3 – Bonticou Crag

Trailhead Location – High Falls, Ulster County

Difficulty – Hard-Extremely Hard

Traffic – Light-Moderate

Trail Directions – A single loop from the Spring Farm Trailhead lot. Take Crag Trail on the way in, and Cedar Trail on the way out. Also on Mohonk Preserve property,

ALSO not for the faint of heart. The trail begins innocently enough, taking you over broad meadows to the “Million Dollar View” of the southern Catskills.

The real fun comes about .9 miles down Crag Trail, where you’re greeted by a cliff of quartz conglomerate slabs. The 150-foot vertical rock scramble can be perilous, but it’s also a great way to see if you’d be interested in more proper rock climbing. If this turns out not to be the case, the top of Bonticou offers ample space to repeatedly cross yourself while panting.

 

#2 – Breakneck & The Cornish Estate

Trailhead Location – Cold Spring, Putnam County

Difficulty – Hard

Traffic – Very Heavy – like, you’ll-see-graffiti heavy

Trail Directions – Take the Breakneck Ridge Trail from Route 9D to the top of Breakneck, then, instead of veering left to the Breakneck Bypass Trail, continue along for a quarter mile to Notch Trail. Notch turns into Brook Trail and leads back to 9D, which you unfortunately have to walk down to get back to the parking lot.

Despite its threatening name, Breakneck is the most heavily trafficked of the trails on this list, due in part to its accessibility from NYC – an hour Metro-North ride to the Breakneck Ridge stop drops you within walking distance of the trailhead. Despite this, it isn’t easy – if you take a tumble during the initial ascent, you’re just gonna keep tumbling.

The pinnacle offers views of Storm King thrusting out of the Hudson River to the west, and Bull Hill to the south. Towards the end of Brook Trail, you come upon the Cornish Estate, which was abandoned in 1938. The area is often misty, and the rock walls rise out of the verdant greenery like Mayan bastions. Check out the greenhouse, but be careful – there’s broken glass EVERYWHERE (because of the greenhouse, not because of jackasses chucking their Coronas).

 

#1 – Pecoy Notch to South Twin Mountain

Trailhead Location – Elka Park, Greene County

Length – 5.6 miles

Difficulty – Hard

Traffic – Nearly Empty

Trail Directions – Take Pecoy Notch Trail 1.6 miles from Dale Road until you reach the second juncture. Go left on Devil’s Path. Hike about 1.2 miles to the peak of South Twin Mountain, then turn around and descend the same way.

This trek brings you to my favorite spot in the Catskills: Dibble’s Quarry, where some maniac – well, probably maniacs – have heaved several tons of rock from the abandoned quarry and constructed a throne room. DIbble’s Quarry is about a mile up the trail.

The highest point on the trail is Twin Mountain, another one of the Catskill 3500 peaks, but continue on for about 25 minutes to South Twin Mountain for one of the best views the Hudson Valley and Catskills has to offer.