Challenging Hikes in and Around Bear Mountain

Bear Mountain State Park is a gorgeous mountain range along the Hudson River. It resides next to Harriman State Park on one side, and when you cross the Bear Mountain Bridge, you get these two gorgeous hikes on Route 9D. These three hikes range in overall difficulty but are not for the faint heart. Yes, the hikes lengths can seem brief, but the elevation and trail challenges are what makes these three perfect for any hiker level.

If you are a novice hiker, I highly recommend any trail you go on, bring someone with you who knows the trail. Bring someone who can navigate the trail and can help ensure a good experience for the hike. I recently completed the Breakneck Ridge trail with a friend, and due to my knowledge of the route, I was able to help her get up the steep elevation.

Each hike ranges in lengths, but here is what you should pack for all the hikes listed below:


Let us jump into these hikes. Leave a comment if you’ve done any of these or plan to. The order of the hikes is alphabetical. It also works out to be the shortest to the longest order. Isn’t that the best when things work out that way?!


Anthony’s Nose (1.9 miles)

Location: Garrison, NY near Bear Mountain Bridge

Distance: 1.9 miles roundtrip

Elevation gain: 675 feet

Difficulty: Intermediate

Pass/permit: No

Dogs: Yes, leashed

Road access: 9D, parking on the side of the road


My boyfriend joined me to complete this hike since neither of us had done it. We’ve been making the most of our weekends by doing a different hike each weekend. This hike was on the list to do for a while. Once we knew we needed a short distance hike, a bit of a challenge, and close to home, Anthony’s Nose was the right fit.


The trailhead is located .3 miles from the Bear Mountain bridge in Garrison, New York, on 9D. Parking for this trailhead in on the road near the trailhead and by the bridge. Be mindful of street signs; in some sections on the road, you cannot park. Also, park with your wheels not on or past the crosswalk on the road; you will be ticketed. Nothing is worse than getting a ticket post-hike!


Don’t be off-put by the short length of this hike. Round trip with taking photos the hike was about 1 hour and 45 minutes. Depending on your hiking skill, this time can be shorter or longer. This trail is sneaky for being strenuous compared to other 2 mile hikes. The first .7 miles of the hike is loose rock and 675 feet of elevation to climb.

We went in November 2020, and the trail had leaves covering the loose rock, which adds to the trail's difficulty. If you have trekking poled, I highly recommend bringing them. They will be useful for balance and to protect your knees.

The trail can be heavily trafficked depending on the time of day and season. Many people underestimate the strenuousness of the hike because of the low elevation and short distance. It is also easy access since it is so close to the bridge.



Expect to stop for people going up or coming down, which can add time to your hike. If you see someone approaching and you have an accessible area to stop, be the one to stop and let the other group pass you and vice versa.

The blazes for this trail are white till you reach the split turn right and follow the blue blazes to the overlook. This final .2 miles will be marked with clear signs telling you where to walk out and where the vista is. The lookout has a stunning view looking right about the Bear Mountain Bridge. This spot has many photos taken at it.


Off to the left, you can see down the Hudson River and different bodies of water. During your time here, you will see many people coming and going if you wait at the summit for some time. There is a decent amount of space at the vista. However, if it is a really crowded day, it can be challenging to find.


From here, make your way back down the blue trail to reconnect to the white blaze on your left. The white blaze will be mostly trekking down. Be mindful of those coming up and lose rock. During the fall, you will also have to deal with leaves, and the loose rocks can be easy to not notice. I was so thankful I had my trekking poles when we completed this hike.


Things to Know Before Hiking Anthony’s Nose:

  • Park over the white line on the side of the road to avoid getting a ticket

  • The trail had lots of loose rocks

  • Short hike

  • Be mindful of others, crowded trail, especially on weekends

  • The expected time average is 2 hours


Breakneck Ridge Trail Loop (3.2 miles)


Location: Cold Spring, NY, Hudson Highlands State Park

Distance: 3.2 miles loop

Elevation gain: 675 feet

Difficulty: Intermediate to Advanced

Pass/permit: No

Dogs: Yes, leashed

Road access: 9D, parking on the side of the road and small lots and Breakneck Ridge Train Stop


This hike I’ve completed about 3 to 4 times, and each time has been so different. This hike seems like a new experience each time I’ve done this hike. The most recent trip to this trail was November 2020 with fellow travel blogger Taylor from Brown Eyed Flower Child. Taylor focuses on boutique travel and gives you the inspiration to travel the world. Check out her recent trip, and thank you, Taylor, for taking photos of me on this hike!

If heights and climbing are something you’re not comfortable with a cliff face nearby, I would be hesitant to recommend this hike to you. However, if you go with someone who knows the trail well, and can help guide you, encourage you, and direct you on the trail, then you can have a safe and enjoyable hike!


I recommend a day lite pack with a bladder for this trip. If you’re going in the fall, something slightly larger since the changing temperatures, you may want something to put a jacket or pullover away in. Since you’ll have points where you’ll need to climb a lite weight pack, and you don’t have to maneuver to climb and walk with is ideal.


Let’s jump into how to find the trailhead. Coming from the Bear Mountain Bridge, the trailhead is about 11 miles down 9D. Thankfully you don’t need to make any turns off 9D—the parking is in lots or on the side of the road. November 2020 was during social distancing, so the lots were blocked off, and the only parking available was on the side of the road to help prevent large crowds.

This trail very well knows that people from all over come to complete it. Since there is a train stop from NYC to the trailhead, you will get plenty of people escaping the city for these scenic views.

At the start of the trailhead, take a physical map or photo to navigate the trail. The Breakneck Ridge Loop is the White trail that goes to red and loops back out on white. The beginning of the trail is the straight elevation gain. There are 3 summit lookouts on the map. I disagree with that. There are more vistas to stop and take in the view.

Go at your own pace. Most people do the scrabble up to the first vista and then leave. That is where the flag and memorial section is that many photos are taken. This stretch is about .5 mile.

Don’t be fooled by the short distance. It is pure elevation and scrambles. If you are not used to climbing up rocks to advance on a hike, do not do this alone. If you are hesitant about your skill level, be sure to have someone there with you to help navigate.

I love this section of the trail. It is a tremendous challenge that makes you really think about where you’re placing your hands and feet. For content, I am about 5’2”, some places I really need to reach and pull myself up. If you are taller than me, you may not have the same issue.

Oh, the way to the second overlook, the trail takes a slight split to the east route or scramble. The blazes to the right is a more challenging route. If you do not want to scramble and not be exposed to the cliff, go the more comfortable way. Both trails bring you to the same destination. One is more favorable to those who do not enjoy heights and are improving their hiking ability.

In this view, you’re looking down at the flag and south. You have gorgeous views of Bear Mountain and the Hudson River curving through the landscape. You almost do not realize how high you are. You're able to tell the elevation increase you’ve accomplished by how far you are from the flag. It's my favorite thing at this lookout.

The next vista is rockier and doesn’t give you a view of the north—your view is of Hudson Highlands State Park. On clear days you can see the Beacon Firetower, another stunning hike in the area I hope to do!


Just before the elevation sign is when the trail turns from a white blaze to a red blaze. There is good signage when you come to this spot. You either continue on the white blaze to the Beacon Firetower or turn left and take the red trail to connect to the white loop back to 9D.

The red blaze is where you’ll do some climbing but nothing like the way up. Thankfully there is nothing too daunting on this loop out. The small section past the elevation sign is a small climb then the trail turns flat.


Most people carry on from this spot to complete to the summit of 1,260 feet elevation that even has a sign! I love it when there is a marker for elevation gain on trails. Doesn’t it just seem so rewarding?


The view is beautiful, but you are more in the tree line. Looking north, you can see an island called Bannerman Castle. In the water, parts of the castle have since been submerged from when it was initially built.

Now is a time where you can take a sigh of relief that the elevation gain is over and enjoy what feels like a pleasant stroll out. When I’ve done this hike in the summer, the trail is easy to see and feels like a short walk out.


When Taylor and I did it this November, it did not feel like a breezy finish. From all the leaves that came down, it was a bit harder to pinpoint loose rocks. I was glad I brought a trekking pole to maneuver through loose rocks and leaves. Fall hikes, I feel, should come with a warning label to bring your trekking poles.

You get a beautiful view north through the trees and get closer to the Bannerman Castle. In the early morning and with some yellow leaves left on the trees, the forest appeared to be glowing.

When you finish the trail, you’re brought back to a different spot than where the trail begins. This is direct across from where the trail station stop is and .3 miles from the tunnel and trailhead. With that distance, choose your parking location wisely!


Things to Know Before Hiking Breakneck Ridge:

  • Arrive early; it is a popular trail, and parking fills up

  • The elevation gain at the beginning is the most challenging part

  • Keep an eye for different routes; these are easier ways up the cliff face

  • Bring plenty of water

  • Expect to take 3 to 4 hours depending on skill level

Popolopen Torne Loop (4.3 miles)

Location: Highland, NY in Bear Mountain State Park

Distance: 4.3 miles loop

Elevation gain: 1,145 feet

Difficulty: Intermediate to Advanced

Pass/permit: No

Dogs: Yes, leashed

Road access: 9W, parking for the full loop


Disclaimer, many people mistake the Popolopen Torne and Timp Torne Trail as the same. If you park on Mine Road and just to 1-mile loop with 479 feet elevation, Timp Torne Trail. Much shorter trail, different parking spots, but I will have a review for that portion after this section.

For this trail, you’ll get to walk along the water, under bridges, on the road, test your trail knowledge for how to find blazes, and use a rope to get up a rock face. This trail is a challenge, which was made more challenging, completing it on a hot August day. A friendly reminder to go early AM if you’re going for a summer hike!

This can be a popular destination, so the parking lot in 9W can fill up; keep that in mind. From the parking lot to the trailhead, it can be very confusing. I used all trails app to find hikes and guidance while on a trail, but I will say you’ll need a printout.


If you’re new to my blog, check out my post about the All Trails fail at Letchworth State Park. From that experience, I highly recommend bringing a printed out map.


You walk left out of the parking lot, and there is a small trail that cuts to Fort Montgomery. After going past the build and take the 1776 trail. The trail starts off with stairs, then go left. The 1776 section is a historical trail connected to the Revolutionary war. I was not aware of that.

Taking this well-groomed trail is the start to not really sure what you’re about to embark on. This is not how the whole trail is. From here, you get to a narrower path that winds along the road that then takes you under the 9W bridge. The body of water next to you is the Popolopen Creek.

After about .1 miles, you walk McCoy Road to the next blaze. Here there is a large rock to note the return to the trail. McCoy Road is a dead-end, so you won’t easily get lost. Once you return to the woods, you will have a gradual 164 fee elevation gain and lose over a total of .4 miles.

In the next section, you walk on the road for a short distance, the is Mine Road, that you cross, you take a .3 mile short cut to step back on to Mine Road for a stretch. The spot can be confusing to find the trail, but keep the All Trail app on for navigation.


When you out of the road, always walk facing traffic. When you get to the road, go right, and the trail will be a distance after the bend on your left after Wildwood Ridge. Here you will be on the trail for 2.1 miles. This area is gorgeous will long stretch till you hit a switchback that gives your legs a good warm-up before coming out to Mine Road to cross and complete Timp Torne Trail.


For that trail review, read the next section. As I’ve mentioned, not all things go correctly on the trail. I forgot the loopback had a different route at the summit, so this review is to be continued! I did love this hike, and I look forward to completing it again in the future.


To avoid my mistake, double-check the All Trails out to help you take the opposite loop out. On the return loop, there is no walking on the road till crossing the 9W bridge. This will bring you back to Fort Montgomery and then the trail back to the parking lot on 9W.

One major unexpected thing that happened when walking back to the parking lot was a reenactment at Fort Montgomery. I had no idea this happened here. The Hudson River was a stunning backdrop.

Things to Know Before Hiking Popolopen Torne Loop:

  • parking in on 9W

  • The hike can take 3.5 to 4 hours

  • Use All Trails for finding loop out from the summit

  • There is a memorial for fallen or soldiers who have passed at the summit

Timp Torne Trail (1 mile)

Location: Highland, NY in Bear Mountain State Park

Distance: 1-mile loop

Elevation gain: 479 feet

Difficulty: Intermediate

Pass/permit: No

Dogs: Yes, leashed

Road access: Mine Road Parking Lot


Part of the Popolopen Torne Loop, this section of that trail, is reviewed here. The beginning starts off with pure elevation gain. This trail does not offer much of a break. It is climbing with loose rock, which added a challenge when completing this in August 2020.


My boyfriend and I went for a challenge to complete this as part of the trail we were doing. This section is on par for the beginning section of Breakneck Ridge to the flag pole. The middle section of the trail is mainly looking for blazes and making sure you’re navigating properly to the summit.


This is a popular trail for the short distance but a known challenge. Be mindful of people coming down as you’re going up and vice versa. There was a short flat section after the middle section, but that brought you to the most fun part! Rocks to climb with ropes to help pull yourself up.

Were these ropes super necessary? No. Did I use them 100%! It made this final stretch before the summit so much more fun.


The summit gives you 360 views of Bear Mountain and Harriman State Park. There is a memorial for fallen soldiers at the summit. When I was there, people were honoring a friend who had passed. Be mindful of being respectful of the monument and those who are coming there for this purpose. It is moving the number of stones that are there.

We did not linger at the summit due to no shade, and the sun felt like it was burning extra strong that day. We went the same route down. This is another trail where trekking poles are recommended to help balance and to protect your knees.


Since breaking my ankle in December 2019, I’ve been more cautious about how I step down trails, and when there is loose rock, I’m extra grateful for the poles to help keep me balanced.

This short trail, I hope, does not disappoint you. Your glutes and calves will be talking to you at the end of it for sure. Return back to Popolopen Torne Loop or get in your car and have a wonderful time in the area.

Things to Know Before Hiking Timp Torne Trail

  • The trail is mainly elevation

  • Loose rocks to add to the challenge of the short distance

  • Summit had a memorial at the top

  • Knowledge of how to read blazes is essential (when you see a blaze midway past should be able to see the previous blaze and next one)


Hudson Valley is a gorgeous area and offers an array of activities. If you’re looking for other relevant blogs post, check out these other blogs post:


Disclaimer, I am not anti solo hiking. Check out my blog post about my solo trip to the Garden of the Gods. It is not my preference, so I will always try to go with a friend. Always practice trail safety and leave no trace. If you have any questions about either, here are helpful links about leave no trace and trail safety. I have been hiking my whole life. If you have any questions to ask, reach out on Instagram! I love connecting and talking about different hikes people have done.


Facts & Attractions of Bear Mountain:

  • Bear Mountain State Park is located in Rockland and Orange County, New York

  • Albany is the capital of New York

  • American currency is in American dollars and cents

  • 5,205-acre state park located on the west bank of the Hudson River

  • State park established 1913


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