Escape the crowds on these hiking trails

By William Benjamin

Cars line both sides of Route 9D all the way from Cold Spring to the bend to Beacon on any given weekend. The Breakneck Ridge Trail is more popular than ever.

“On busy days it’s over a thousand hikers a day,” said Hank Osborn, senior program coordinator for New York–New Jersey Trail Conference (NYNJTC.) “The trails are getting overused and there is lot of erosion from the hikers.”

And, why shouldn’t it be crazy popular? The Hudson Highlands are gorgeous and have been the inspiration for painters, writers and Instagram-ers alike. Sharp, powerful mountains rise boldly from the slow and curving water. They defy the gentle roll of the encompassing hills; these are the New York fjords.

“Breakneck is the perfect storm for a popular hiking trail, because the terrain is challenging, the views are spectacular and social media makes it very accessible from New York City,” said Osborn.

But, who wants to hike in single file, hear iPhone Electro Disco and send a Snapchat that their friends have already seen?

If you want to get out on a trail, clear your head and build a thirst for a barley soda, then here are six alternative hikes for escaping the crowds. Happy trails.

Drew Grabfield looks out over West Point from the Revolutionary War–era South Redoubt. Photo by W. Benjamin
Drew Grabfield looks out over West Point from the Revolutionary War–era South Redoubt. Photo by W. Benjamin

North and South Redoubt: Revolutionary War Heritage Trails
(moderate, 2.4 miles, 2 hours)

Legend has it that George Washington followed this trail to visit his garrisons stationed on the two Revolutionary War forts that overlook the river. As once- strategic points to bombard enemy ships coming up the Hudson, this trail offers great views of the river in both directions. This has the best vista of West Point and the 90-degree bend in the river called World’s End. Vegetation blocks some of the spectacular scenery, especially in the summer, but increased traffic may inspire more diligent maintenance.

Start from the new parking lot on Snake Hill Road, across from the Walter Hoving Home, and follow the trail blazed with red markers. After a few switchbacks, the trail forks; North Redoubt is to the right and South Redoubt is to the left. This trail is never crowded.

Sugarloaf Hill
(moderate, 3.2 miles, 2 hours)

This trail is in the shadow of Osborn Castle, which looks like something out of a fairy tale. Although the castle cannot be seen from the top of Sugarloaf, there is plenty else to take in — Anthony’s Nose, Bear Mountain and the beautiful bridge.

The trail starts from a parking lot up the Wing and Wing driveway (across 9D from the water tower in Garrison). Follow the sign that says “hikers this way,” and keep an eye out for red trail markers. The trail goes through a field (be ever vigilant about deer ticks) before taking off uphill. There is a gazebo along the wooded slope that may be a nice place to catch one’s breath and reflect on the serenity of nature.

Anthony’s Nose
(moderate/difficult, 3.6 miles, 3 hours)

Anthony’s Nose? That’s just as much of a madhouse as Breakneck, right? Yes and no. It depends on how you approach it. Most hikers come straight up from 9D, which is more challenging and crowded. Instead, start from the South Mountain Pass trailhead, where the Appalachian Trail crosses the no-longer dirt road. There is a pull-off on the south side of the road and a swinging gate where the trail begins. The more gradual and easier ascent follows an old road to Camp Smith and then bends right, just before the military reservation. For more of a challenge, follow the white markers, which is the AT, and veer from the old road a few hundred yards from South Mountain Pass.

The rocky outcropping at the top of Anthony’s Nose offers unrivaled views of the Bear Mountain Bridge and the river flowing south. There are many viewpoints from on top, so take some time to wonder around. It is a beautiful spot for a picnic, though often crowded from hikers coming up from 9D.

Fishkill Ridge Conservation
(difficult, up to 11.5 miles, 3–7 hours)

Bite off as much as you can chew. The Fishkill Ridge trails offer 11.5 miles of hiking through the Hudson Highlands. At times strenuous, with steep changes in elevation, the trail is not for those looking for a casual stroll. This trail is even more challenging than Breakneck. Bring a backpack full of snacks and water, and make a day of it. Along the trail there are lookout points that face all directions, including one with a glimpse of the New York City skyline.

There are a couple options for how to approach the trail. Trailheads start at Pocket Road in Beacon, Sunnyside Road in Beacon Hill, and somewhere up on Route 9
(I don’t want to divulge too many secrets).

Looking across the river from Arden Point in the late afternoon; photo by W. Benjamin
Looking across the river from Arden Point in the late afternoon;
photo by W. Benjamin

Arden Point and Marcia’s Mile
(easy, 2.2 miles, 1.5 hours)

Best known to any high school student in Philipstown as the way to Flat Rock, Arden Point and Marcia’s Mile provide a different perspective of the river. This trail stays close to the train tracks before it crosses a bridge over them that heads to the water. There are many little trails on the west side of the tracks, both official and unmarked. It’s nearly impossible to get lost, and there are plenty of points to look out over the water or jump into it. A gazebo sits on a wooded ridge on the east side of the tracks, less than a mile south of bridge. It’s a great place to walk a dog or decompress after a stressful day at work.

One trailhead starts at the south end of the Garrison train station. It is easy to follow and heads past a few dilapidated brick structures. Another branch of trails comes down from the Philipstown Recreation center.

Denning’s Point
(easy, 1.2 miles, 1–2 hours)

Denning’s Point Trail loops around a small peninsula that darts into the Hudson River. The whole time, the hiker never strays more than 20 yards from the water. This walk is easy, relaxing and a great place to escape into vegetation. There are plenty of logs to sit on and read, plus a sandy beach to skip rocks and see the action on the river. The east section of the trail is a great place to watch birds.

Looking south along Denning's Point Trail; photo by W. Benjamin
Looking south along Denning’s Point Trail; photo by W. Benjamin

Another draw to this trail is that it is close to Beacon. After the loop, head to Main Street for food, or the Denning’s Point Distillery, just because it shares the same name. The City of Beacon has gone through a renaissance and is a great place to find craft beer and a bite to eat. Follow signs to Denning’s Point from Route 9D, and signs to Main Street from Denning’s Point. It’s all well marked.

For more trail information, check out

Behind The Story

Type: News

News: Based on facts, either observed and verified directly by the reporter, or reported and verified from knowledgeable sources.

William Benjamin is a former Garrison resident.

11 replies on “Six Alternatives to Breakneck”

  1. Really? You want the hordes to come to these delightful, quiet little gems and transform them to Breakneck alternatives? In a short matter of time they will be eroded by those who won’t stay on marked trails, littered by people too lazy to take their own trash, graffiti on every available rock outcropping, unprepared hikers needing to be rescued, etc.?

    Articles like these are what created the destruction of Breakneck and now we should move that chaos further south? Please keep these gems a great secret for area residents and let the thrill-seekers continue their unchecked destruction of Breakneck. Or, do the smart thing and charge $10 a person to access the trails and use the money to mitigate their overuse.

  2. I agree it is time to find a way to charge for the use (and mis-use) of our natural resources. When things don’t cost enough people tend to think of them as having no value and treat them as such.

  3. I’m an advocate for all to enjoy the bounty that the region brings but not at the expense of it. I believe as a result of the misuse and overcrowding stricter regulation should be created and enforced. Breakneck, Little Stony Point and more recently Anthony’s Nose have created a dangerous situation on the trail and roadside as well as a disposal area for hikers’ trash.

    Perhaps we should consider limiting parking spaces and installing solar powered pay and display machines. We may also want to consider signage stating there is no parking beyond this point as well as signage educating hikers on the principles of Leave No Trace and the fine for littering. The money from parking could then be used for trail maintenance and sustainability.

    A longer term solution may be to create more fee-based parking but that requires land and a greater amount of financing, not to mention the impact on the environment. One thing I believe most residents of Philipstown can agree upon is something needs to be done sooner than later.

  4. Here’s a thought: instead of encouraging the hikers, how about trying to get more shoppers to come visit Cold Spring? All that outdoor stuff is highly overrated, plus we have an amazing bunch of fabulous stores on Main Street. Not to mention our many fine restaurants and eateries that have something for every budget and taste. I say let’s keep all the local natural wonders a secret and get the word out about beautiful, downtown Cold Spring, a shopper’s gourmet paradise.

  5. All fair points ladies and gents, but I think you overestimate the power of the written word these days, and are unable to appreciate the insanity that is Breakneck. It wouldn’t be the worst thing in the world if 50 people got off of Breakneck and went on one of these trails. Don’t worry, as any Philipstownian knows, there are many more gems. Some of these trails are lacking proper maintenance and could use some more publicity. Get out, enjoy the Hudson Valley, spend money at the local businesses, and, most importantly, Happy Trails.

    1. It’s not the power of the written word. The written word only goes out to a few people — it’s the power of the Internet to transform everything it touches. And once opened the genie does not go back in the bottle.

  6. I love the idea of publicizing alternatives to Breakneck, which has become a freak show on most summer weekends. I could only wish that the article mentioned the opportunities on the other side of the bridge, Storm King Mountain and Black Rock Forest. Both are phenomenal.

  7. Shop owners might do well to note that the natural beauty of our Cold Spring surroundings is what draws people to visit in the first place. As an added benefit, there are unique and interesting shops to visit as well.

    I would never characterize our local scenery and outdoor activities as overrated, and I doubt the Hudson River School of artists (past and present) would, either.

  8. I couldn’t agree more with a lot of the responses here. And the fact that this shows up in the sidebar as the most popular post on at the moment, sort of proves the point on the power of the Internet.

    Why would anyone want to send the masses that have overrun Breakneck and Little Stony Point to some of our other, less crowded local treasures?

    And as for the natural beauty of the region drawing shoppers and diners to Cold Spring’s Main Street – the closing paragraph of the article suggests that they do just that – but in Beacon!

  9. Before the joys of hiking met social media the number of hikers on Breakneck could fit into Guinan’s phone booth. Breakneck has been transformed with Anthony’s Nose right behind it. Well intentioned though it may be, it’s hard for me to see how “flooding the zone” with more trail recommendations posted to the web should come before a solid crowd-management plan.

    I’m a hiker, it’s not my only passion, but I definitely enjoy the land and a nice hike with family or friends. One trail that was recommended in a recent article to shed traffic from Breakneck is the sensitive South Redoubt site in the Garrison School Forest.

    It was suggested how that trail and site might be better maintained if more hikers went there. Maybe, but the evidence at Breakneck proves that more than 1,000 per weekend day does not repair trails etc. It takes interested people with time to work these trails.

    When school starts I’ll propose to the Garrison School Board an update to the South Redoubt Reclamation Project from 2001. It will include a new living plan to manage the site in the Garrison School Forest going forward. Local trail volunteers will attest to the difficulty of keeping their initial work intact. For example, in 2001 with the insights from 15 subject-matter experts ranging from American history, forestry and engineering, our team was given authority by the Garrison School to reclaim the South Redoubt site and the related trail in the Garrison School Forest.

    At that time you couldn’t even see the sky through the trees. The work required felling a large number of red oak, ash, locust, choke cherry, and invasive species like Norway maple along with saplings, brambles, smaller growth, sumac, vines etc. The heavy cutting would take the team many months as the site was a half-mile uphill. If they missed a ride they would walk uphill over a half-mile with chain saws, fuel and tools, Once the large trees were down and cut, saws and chippers were put away and the next wave of workers completed the clearing. The site and trail work was supported by many women, men and children.

    The first three phases were completed by the Spring of 2003. South Redoubt was an outdoor classroom with a living history class for students. Some classes would ascend the trail, don woolen uniforms and consider the hardships and commitment of those first patriots.

    This is a nice hike but a highly sensitive and historic site to handle waves of unmanaged random hikers. I will be asking the school to consider and approve my proposal for a living plan and help the site recover.

    Hiking the land here is a great activity. But inviting large crowds requires planning, hygiene facilities, and common standards long before they arrive. Reading the thoughtful posters here and the concerns of the NYS Parks staff I sense there is movement in this direction. Without a good plan in place social media can “flood the zone” and may reduce the joy of hiking to walking in the woods in a long line.

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