Challenging Hikes New York

Fall Palisades Hike

Take the Great Saunter Fall Challenge. [Register here](https://shorewalkers.org/join-a-saunter/) to walk 32 miles over 16 days, starting Oct. 3. Help Shorewalkers support our parks by donating $10 to participate, with all fees going to [Riverside Park Conservancy](https://riversideparknyc.org/) This walk will count for 20 miles of your total. Join us for a 20 mile hike stretching from upper Manhattan to the town of Nyack in Rockland County. We will start by crossing the GWB and then will follow the Long Path trail heading north along the palisades. On our walk we’ll see beautiful wooded paths and stunning views of the Hudson River. This will be a moderately paced hike with minimal breaks, as we’ll need to keep on a tight schedule to finish on time. While the path is mainly flat, you should expect rocky trails, stairs and a few steep hills. Hiking shoes are required and poles are strongly recommended. There are no dropout points where public transportation is easily accessible on this hike so consider your ability to complete 20 miles before signing up. Previous hiking experience is necessary. Meet at 8:00 at the GWB Bus Terminal in the waiting room on the upper level. We will leave promptly at 8:15. Do not come late because we cannot wait. Our hike ends in Nyack where you can take the H07 bus to Tarrytown and catch the Metro North back to the city. There is also the option of taking a Coach bus back to the GWB bus terminal. Please check transportation schedules ahead of time. Bring water, lunch and snacks. We will have a lunch stop at State Line Lookout. Food and beverages are available for purchase there. Contact hike leader Jessica with any questions: 347-603-8447 Co-Hosts: Iris & Fernando

No small talk hike for founders

## The No Small Talk Hike **For founders and people who are interested in business & physiology / philosophy** Going for a hike causal conversations sharing life experiences * What are you building, and what would you lose if it worked? * When did you last change your mind about something that mattered? * What do you believe that most of your peers would disagree with? * Is ambition a virtue, or a very respectable form of avoidance? * What would you do if you knew you couldn't fail, and what if you knew you couldn't be seen? **Who it's for** Founders, operators, and builders who want conversation with some weight, and anyone who reads philosophy, argues about it, or just likes thinking out loud. You don't need a company or a reading list. **The details** * **When:** Sunday 11th October at 10am * **Where:** Cold Spring, New York * **Distance:** 2 hour hike * **Bring:** Water, comfortable shoes * **Cost:** Free

Tentative Upstate Carpool Hike in Harriman State Park - 8 miles

This will be our first hike off of Long Island (lower Hudson Valley to be exact). The name of the hike is Big Hill, Break Neck Pond, Ladentown and Reservoir Loop located in Harriman State Park. If you are available on October 17th and are seriously interested in joining the group for this moderately challenging 8 mile hike, please contact me directly before entering your RSVP. Greg 631-275-0512 I am limiting attendance to 10-12 members. I will consider more than 12 participants if we have additional people who want to drive their vehicles. if you are a passenger you are required to chip in $10 to cover the driver's gas and tolls. The trail entrance is 72 miles from my home in East Northport. The plan is to carpool in 3 vehicles beginning at 8am so we can arrive at the trail no later than 10am. After the hike, we will eat lunch at a local restaurant and then head back to Long Island between 4 and 6pm. I look forward to hearing from any interested parties. Greg 631-275-0512

Saturday Oct 10th Forest Park Hike.

\*\*\* CHECK HERE BEFORE GOING \*\*\* Rainy weather may cancel hike Meet time is 10:30AM, hike start is 10:45AM. Duration is about 2 hours + or - a few minutes. We will hike along several of the many trails in the woods. Wear heavy shoes or boots as the trails are rocky and have many tree roots. Distance is a about 4 miles plus or minus a bit. Hile will be led by Werner and Jerry Attendance is at your own risk, and by joining, you agree to hold us not responsible for any accidents, injuries, losses or unforeseen problems that may arise. This includes contamination by any germs, viruses, or any other illnesses. If the grouping, numbers of attendees and distances get too close, we will break into two separate groups. This should satisfy any limitations on numbers of hikers and distancing. The hike is free ,but we would like to ask for a voluntary donation of whatever you want, or one $ 1 or $2 to help cover the fee Meetup charges us to use their website.

Eastern Devil's Path, with transportation

**PLEASE NOTE: THIS IS A PRE-PAY ONLY EVENT** Please read carefully: This event is being hosted by Adventure Untamed (https://www.adventureuntamed.com/trip/eastern-devils-path-3/). **Please register directly through the website**. **You spot will only be held once you register and pay through the Adventure Untamed website.** **Transportation and licensed guides are included in the cost of the trip. All you have to do is show up!** **You must have Catskill 3500 (or equivalent) peak experience before attempting this trip. Please email info@adventureuntamed.com with any questions.** Looking for a challenge? Hike the eastern half of the infamous Devil’s Path! Known as one of the most challenging hiking trails in the Northeast, the Devil’s Path has steep, rugged ascents and equally difficult descents, slowing down the pace of even the most experienced hikers. Conquering the eastern half will require you to scramble up rocky trails and navigate boulders and gravel on the descents. But we’ll be there to set you up for success! You will have access to a resupply and bail out point (after approximately 8 miles and three peaks), and our guides will be on trail to help throughout the day. And if you are feeling up for a really intense day, join us to hike the full Devil’s Path – we do it every summer! This is an **at-your-own-pace** hike. Guides will be sweeping and at timed cutoff checkpoints to ensure everyone’s safety! On this trip we will summit Indian Head, Twin, Sugarloaf and Plateau mountains. These are required peaks for [Catskill 3500 Club Membership](https://www.adventureuntamed.com/3500-club/). **What’s included**: * NY State Licensed and Wilderness First Responder Certified Guides * Transportation to and from NYC * Resupply, and bail-out point, and trail support as you attempt one of the most challenging hikes in the Northeast [Cancellation Policies](https://www.adventureuntamed.com/info/?tab=2) **Wear** * Hiking boots (**required**) * Weather-appropriate, moisture wicking, althletic clothing (**no cotton**) * Wool or synthetic socks (**no cotton**) * Hat * Sunglasses **Pack** * Lunch * Ample Snacks * At least three (3) liters of water * Backpack * Sunscreen * Bug spray * Fully waterproof top and bottom layers that can be worn over all other layers * Extra layers to adjust for changing weather condtions * Extra pair of wool socks * Headlamp * Trekking poles (optional) * A change of clothes for the ride back (optional) **Level:** INTENSE (https://www.adventureuntamed.com/info/?tab=1) **Mileage:** \~12 miles **Elevation Gain:** \~4,600 feet **Group Size:** 2 - 13 adventurers

Autum/Halloween Hike & Lunch🍁🍂😨

Sunday Hike: Cats Rock

**To attend this event, simply RSVPing on Meetup isn’t enough — you must book through our website to secure your spot.** **TO ATTEND YOU MUST BOOK ► [HERE](https://outyork.com/new-york-hiking-tours/cats-rock-10-11-26/)** **EXPLORE MORE ADVENTURES HERE ►** **[Upcoming Events](https://outyork.com/new-york-hiking-tours/)** **Cats Rock** **Cats Rock Trail, part of the famous Appalachian Trail, offers a moderate to hard hike through dense woods and scenic vistas.** As you climb, you’ll be surrounded by towering trees and rewarded with breathtaking panoramic views at the summit. Perfect for those seeking a nature escape or looking to meet new outdoor enthusiasts. A challenging yet rewarding adventure in the heart of the wilderness. Pack your favorite sandwich and drink, we will have a snack break on the trail. ***This is a Continuous Pace Hike:*** *We’ll take breaks along the way, but not as often as on other hikes, since we need to maintain a steady pace to catch the train. Please note that transportation for this hike is limited, with departures only every two hours.* 🗺️ About the Hike * Small Group Experience: 2 - 15 OutYorkers. * Hiking Route: [AllTrails Map](https://www.alltrails.com/es/explore/recording/afternoon-hike-e2a7555--474?u=i&sh=ypq48e) * Difficulty: Moderate. The perceived difficulty may increase if you are a beginner hiker or not physically active. * Elevation Gain: 1,358 ft. (413 mt) * Highest Elevation: 1,171 ft. (357 mt) * Lowest Elevation: 430 ft. (131 mt) * Hiking Distance: 6.5 mi. (10.8 km) * Hiking Time: 3h 30m. This could change according to the group pace. ✅ **Included:** **Hike led by a New York State licensed wilderness guide.** ❌ **Not Included:** Train ticket or any other services or products not mentioned. **EXPLORE MORE ADVENTURES HERE ►** **[Upcoming Events](https://outyork.com/new-york-hiking-tours/)**

Sunday Hike: Bull Hill

**To attend this event, simply RSVPing on Meetup isn’t enough — you must book through our website to secure your spot.** **TO ATTEND YOU MUST BOOK ► [HERE](https://outyork.com/new-york-hiking-tours/bull-hill-10-25-26/)** **EXPLORE MORE ADVENTURES HERE ►** **[Upcoming Events](https://outyork.com/new-york-hiking-tours/)** **Bull Hill** **Take on the challenge of this challenging hiking trail in New York’s Hudson Valley**, known for its steep ascents and rugged, rocky terrain. While demanding, the journey is well worth it, as you’ll be rewarded with awe-inspiring views of the Hudson River and surrounding landscapes. Perfect for experienced hikers seeking a physical challenge paired with breathtaking scenery, this trail is a must for your next outdoor adventure. We will have a snack break on the trail. **We’ll wrap up our adventure at a cozy local pizzeria**, where we can relax, enjoy some food and drinks, and spend time chatting and connecting with fellow adventurers. *We’re getting away from the city to forget about timing, enjoy nature, and connect with others. If you’re looking to make new outdoorsy friends, you’ve found the perfect place. If you’re seeking a fast-paced group, this might not be the right fit.* 🗺️ About the Hike * Small Group Experience: 2 - 15 OutYorkers. * Hiking Route: [AllTrails Map](https://www.alltrails.com/es/explore/recording/afternoon-hike-bull-hill-short-loop-ffac735) * Difficulty: Challenging. The perceived difficulty may increase if you are a beginner hiker or not physically active. * Elevation Gain: 1,138 ft (347 mt) * Highest Elevation: 1,099 ft (335 mt) * Lowest Elevation: 16 ft (5 mt) * Distance: 4.60 mi (7.5 km) – This doesn't include the 1 mile (1.6 km) walk from the train station to the trailhead. * Hiking Time: 4h. This could change according to the group pace. ✅ **Included:** **Hike led by a New York State licensed wilderness guide.** ❌ **Not Included:** Train ticket or any other services or products not mentioned. **EXPLORE MORE ADVENTURES HERE ►** **[Upcoming Events](https://outyork.com/new-york-hiking-tours/)**

Thursday Hike: Breakneck Ridge

**To attend this event, simply RSVPing on Meetup isn’t enough — you must book through our website to secure your spot.** **TO ATTEND YOU MUST BOOK ► [HERE](https://outyork.com/new-york-hiking-tours/breakneck-ridge-10-22-26/)** **EXPLORE MORE ADVENTURES HERE ►** **[Upcoming Events](https://outyork.com/new-york-hiking-tours/)** **Breakneck Ridge** **Discover Breakneck Ridge, one of the most iconic hikes in New York, located in the stunning Hudson Valley just outside NYC.** This moderate and adventurous trail rewards hikers with scenic paths and unforgettable views of the Hudson River and surrounding mountains. Ideal for travelers eager to explore nature beyond New York City, the hike starts and ends in Cold Spring, a charming town. **We’ll wrap up our adventure at a cozy local pizzeria**, where we can relax, enjoy some food and drinks, and spend time chatting and connecting with fellow adventurers. *We’re getting away from the city to forget about timing, enjoy nature, and connect with others. If you’re looking to make new outdoorsy friends, you’ve found the perfect place. If you’re seeking a fast-paced group, this might not be the right fit.* 🗺️ About the Hike * **Small Group Experience:** 2 - 15 OutYorkers. * **Hiking Route:** [AllTrails App](https://www.alltrails.com/es/explore/recording/afternoon-hike-at-breakneck-ridge-ac4d175) * **Difficulty:** Moderate. The perceived difficulty may increase if you are a beginner hiker or not physically active. * **Elevation Gain:** 1,073 ft (327 mt) * **Highest Elevation:** 987 ft (301 mt) * **Lowest Elevation:** 20 ft (6 mts) * **Hiking Distance:** 5 mi (8 km) – We'll walk an extra mile (1.60 Km) from the train station to the trailhead. * **Hiking Time:** 4h 30m. This could change according to the group pace and includes a leisurely stroll around Cold Spring’s waterfront and charming streets. ✅ **Included:** **Hike led by a New York State licensed wilderness guide.** ❌ **Not Included:** Train ticket or any other services or products not mentioned. **EXPLORE MORE ADVENTURES HERE ►** **[Upcoming Events](https://outyork.com/new-york-hiking-tours/)**

Hike Garrison, Anthony's Nose to Manitou

We'll hike from Garrison station to Manitou station through wooded forest, with views of the Hudson River from Anthony's Nose. You should be in GOOD AEROBIC CONDITION for this hike, it's around 11.5 - 12 MILES. There won't be any crazy rock climbs, but a good opportunity to log some miles without the crowds. There's lots of trains back to the city if you have plans for Saturday evening. Feel free to bring friends who aren't in the group. **TRAIN FROM NYC:** We'll meet at the clock/information booth in the center of Grand Central at 8:30am. Buy your roundtrip ticket to Garrison (both Manitou & Garrison are in fare zone 7). We'll take the 8:56am Metro North train arriving at Garrison 10:12am. Return trains from Manitou are at 3:13, 3:32, 4:29 and 5:17pm. **DRIVERS:** This hike STARTS and ENDS at different places. It starts at the Garrison train station at 10:12am Here's the Google pin [https://maps.app.goo.gl/ncyHUnUH25LKfFbA9](https://maps.app.goo.gl/ncyHUnUH25LKfFbA9) It ends near the at Anthony's Nose Trailhead [https://maps.app.goo.gl/2rKAKunaFw9hDE2V9](https://maps.app.goo.gl/2rKAKunaFw9hDE2V9) We can discuss in the comments in Meetup app how to get you back to your cars at the end of the day. **FOOD:** There are NO restaurants or stores at either train stations, so bring plenty of water and a hearty lunch and a snack for the train ride back. **GEAR:** Hiking boots or trail runners, warm layers and a rain shell are suggested. Bug spray is good to keep ticks away. **MAP:** Here's an AllTrails map of our route: [https://www.alltrails.com/explore/custom-routes/custom-route-1015374?u=i&sh=y5kkrh](https://www.alltrails.com/explore/custom-routes/custom-route-1015374?u=i&sh=y5kkrh) AllTrails is a great app and can help you from getting lost. Highly recommended. I posted a pic of the map in the photos too. Here's my AllTrails profile. If you follow me it's easier to find the maps [https://www.alltrails.com/members/william-wilson-16](https://www.alltrails.com/members/william-wilson-16) Any questions contact me, Bill Wilson

Monday Hike: Bull Hill

**To attend this event, simply RSVPing on Meetup isn’t enough — you must book through our website to secure your spot.** **TO ATTEND YOU MUST BOOK ► [HERE](https://outyork.com/new-york-hiking-tours/bull-hill-10-12-26/)** **EXPLORE MORE ADVENTURES HERE ►** **[Upcoming Events](https://outyork.com/new-york-hiking-tours/)** **Bull Hill** **Take on the challenge of this challenging hiking trail in New York’s Hudson Valley**, known for its steep ascents and rugged, rocky terrain. While demanding, the journey is well worth it, as you’ll be rewarded with awe-inspiring views of the Hudson River and surrounding landscapes. Perfect for experienced hikers seeking a physical challenge paired with breathtaking scenery, this trail is a must for your next outdoor adventure. We will have a snack break on the trail. **We’ll wrap up our adventure at a cozy local pizzeria**, where we can relax, enjoy some food and drinks, and spend time chatting and connecting with fellow adventurers. *We’re getting away from the city to forget about timing, enjoy nature, and connect with others. If you’re looking to make new outdoorsy friends, you’ve found the perfect place. If you’re seeking a fast-paced group, this might not be the right fit.* 🗺️ About the Hike * Small Group Experience: 2 - 15 OutYorkers. * Hiking Route: [AllTrails Map](https://www.alltrails.com/es/explore/recording/afternoon-hike-bull-hill-short-loop-ffac735) * Difficulty: Challenging. The perceived difficulty may increase if you are a beginner hiker or not physically active. * Elevation Gain: 1,138 ft (347 mt) * Highest Elevation: 1,099 ft (335 mt) * Lowest Elevation: 16 ft (5 mt) * Distance: 4.60 mi (7.5 km) – This doesn't include the 1 mile (1.6 km) walk from the train station to the trailhead. * Hiking Time: 4h. This could change according to the group pace. ✅ **Included:** **Hike led by a New York State licensed wilderness guide.** ❌ **Not Included:** Train ticket or any other services or products not mentioned. **EXPLORE MORE ADVENTURES HERE ►** **[Upcoming Events](https://outyork.com/new-york-hiking-tours/)**

Reverse Saunter — 34 miles

**Take the Great Saunter Fall Challenge! [Register here](https://shorewalkers.org/join-a-saunter/) to walk 32 miles over 16 days, starting October 3rd. Help Shorewalkers support our parks by donating $10 to participate, with all fees going to the [Riverside Park Conservancy](https://riversideparknyc.org/). This walk will count for *all* of your total miles!** Enjoy a fun & challenging walk along the epic Great Saunter course *in reverse* from East Side ➔ West Side. This walk is offered as part of the **[Great Saunter Fall Challenge](https://shorewalkers.org/great-saunter-fall-challenge/)**. **Meet** 7 am inside Whitehall (Staten Island Ferry) Terminal (2nd level, by the toilets). We start walking @ 7:15. *Check for transit service changes before leaving home!* **Late arrivals** contact a leader; get to a location ahead of the group; tell us where to find you. **End** Whitehall (Staten Island Ferry) Terminal. Congratulations! Eat & drink with us afterwards to celebrate! **Route & Pace**: Starting at Whitehall (Staten Island Ferry) Terminal, we walk north along the east side of Manhattan, enjoy a short break in Inwood Hill Park, then continue south along the west side back to South Ferry. 34 miles at a fast pace (3.5 mph); about 12 hours including toilet & rest stops. **Note** unlike the Great Saunter — an individual challenge you walk at your own pace — we will walk the Reverse Saunter together at a brisk pace. **Map** use the [Great Saunter Digital Map](https://map.shorewalkers.org/) on your mobile device. Grant permission to monitor your location along the route. Use Komoot, Strava, or AllTrails to record your epic adventure. *We will deviate from the May Saunter route at several points.* **Rain date** If heavy rain is forecast, we’ll postpone one week to October 17. **Bring** drinks, hydration salts, snacks, hat, sunscreen, portable charger, and clothing layers to adjust to the day's changing temperatures. Pack sunglasses: *the sun will be in our faces for much of the day due to the reverse course*. **Snacks & Hydration** water fountains are scarce — especially on the East Side. Places to buy drinks & snacks are scarce — especially after Inwood Hill Park. Plan accordingly to prevent dehydration, electrolyte imbalance, etc. *Alert a leader before your supplies run low*. **Toilet Stops** Whitehall Terminal (before walk), St. Vartan Park (E 35th St), Carl Schurz Park (E 84th St), Frederick Johnson Playground (W 150th St), Inwood Hill Park, 72nd St., Pier 84 (44th St), Chelsea Piers, Whitehall Terminal (after walk). *Alert a leader if you need an unscheduled toilet stop*. **Drop-out points** all along the route in case you tire or are unable to keep up with the main group. *Alert a leader if you decide to drop out*. **Preparation, Health, and Safety**: Attempt this walk only after completing the appropriate fitness training in the weeks before the walk. Not suitable for slow walkers. Stay ahead of the sweep. Watch for bikes in both directions. No dogs. Pack a care kit if you're prone to blisters. *Alert a leader if you need to stop to care for your feet or attend to another health concern*. **Achtung** *change your RSVP promptly if you cannot attend*. Habitual late-cancelers & no-shows will be purged from the going list. Look the part by getting your **[Great Saunter Fall Challenge merch](https://bigfroguws.chipply.com/ShorewalkersNY/store.aspx?eid=364394&acid=1777491)** at our store. *Fall Challenge participants*: remember to print your bib with any number you like. **Leader** Dan D [msg on Meetup] **Co-host** Sheila Chung Many thanks to our Aug 29 & Sept 5 advanced scouting volunteers! Event guests must sign Shorewalkers' [Waiver and Release](https://app.waiversign.com/e/659a09c1b851170012c1225c/doc/659a0cdf15c42c0012f2cdc3?eventName=Shorewalker%20Walks%202025) to participate.