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

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: 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/)**

Fun Fall Hike and Halloween Parade

Let’s go on a fun fall hike to see the changing foliage! We will meet at Grand Central terminal and take the Metro North to Yonkers where we will start our hike on the Old Croton Aqueduct Trail. We will follow the trail to the village of Tarrytown where they will be holding their annual Halloween parade beginning at 5:00. You can stick around to watch the parade or catch the Metro North back to the city. Early dropouts via the Metro North are also available. Please note that we will maintain a brisk pace in order to arrive in time to see the parade. Consider your ability to hike this distance with minimal stops before applying. Meet at Grand Central Station in front of the information booth at 10:30 am to catch the 10:53 am Croton Harmon train. We will take this train to the Yonkers station, arriving at 11:26. Total distance is approximately 14 miles. Bring water, lunch and snacks. Bug spray is also recommended. Heavy rain cancels. Contact hike leader Jessica day of the walk with any questions: 347-603-8447

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/)**

Sunday Hike: Sky Top [Transportation Included]

**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/sky-top-10-18-26/)** **EXPLORE MORE ADVENTURES HERE ►** **[Upcoming Events](https://outyork.com/new-york-hiking-tours/)** **Sky Top** **Experience one of New York’s most rewarding hikes with a steady uphill climb leading to breathtaking summit views over the Shawangunk Ridge.** Enjoy the same iconic scenery as the Lemon Squeeze—without the narrow passages—while spotting soaring eagles and unique rock formations along the way. After the summit, descend along the peaceful shores of Lake Mohonk, where forested paths and tranquil waters create the perfect finish. This hike blends adventure, stunning views, and relaxation into an unforgettable outdoor escape. Pack your favorite sandwich and drink, we will have a snack break on the trail. *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 - 20 OutYorkers. * Hiking Route: [FootPath Map](https://footpathapp.com/routes/3175d4c9-0b48-4e50-934b-29030a6a2931) * Difficulty: Moderate - Challenging. The perceived difficulty may increase if you are a beginner hiker or not physically active. * Elevation Gain: 1,158 ft. (353 mt) * Highest Elevation: 1,542 ft. (470 mt) * Lowest Elevation: 452 ft. (138 mt) * Hiking Distance: 5.59 mi. (9 km) * Hiking Time: 3h 30m. This could change according to the group pace. ✅ **Included:** **According to Selected Package.** ❌ **Not Included:** Anything not mentioned in the selected package. **EXPLORE MORE ADVENTURES HERE ►** **[Upcoming Events](https://outyork.com/new-york-hiking-tours/)**

Advanced Hike Wittenberg & Cornell

**MUST REGISTER HERE TO ATTEND [https://joinoutsiders.com/events](https://joinoutsiders.com/events)** This one is for the seasoned hikers. Join us for a challenging, high-reward trek up two of the Catskills' most iconic peaks, Wittenberg and Cornell, deep in the Slide Mountain Wilderness. It's a demanding day on the trail, and the payoff is one of the most jaw-dropping views in the Northeast: the sweeping panorama of the Ashokan Reservoir and the surrounding high peaks from Wittenberg's summit ledges, framed by peak fall color. We'll climb the classic Burroughs Range route from Woodland Valley, gaining serious elevation through hardwood forest and stands of spruce and fir before topping out on Wittenberg, then pushing on to the rocky summit of Cornell (including the famous "Cornell Crack" scramble). This is a strenuous, full-commitment hike with steep, rugged terrain, so come prepared and ready to earn the view. **EVENT TIMELINE** * 9:00 AM: Meet at The Standard Biergarten (Meatpacking) * 9:30 AM: Depart NYC * 11:30 AM: Arrive at Woodland Valley trailhead and begin hike * 2:00 PM: Summit Wittenberg, lunch and photo break at the overlook * 3:00 PM: Push on to the summit of Cornell * 3:45 PM: Begin descent * 6:00 PM: Complete hike and regroup * 6:30 PM: Head to a local eatery for food and drinks * 8:00 PM: Depart back to NYC * 10:30 PM (approx.): Arrive back in the city All timing is approximate and subject to change based on group pace and conditions. ## **WHAT'S INCLUDED IN YOUR TICKET** * Roundtrip transportation from NYC * Guided hike led by OUTSIDERS hiking guides * Parking and trail access fees * Complimentary water and beverages on the ride home ## **HIKE DETAILS** * Trail: Wittenberg and Cornell via the Burroughs Range (from Woodland Valley) * Location: Catskill Park, Slide Mountain Wilderness * Mileage: approx. 9.4 miles (out and back) * Elevation Gain: approx. 2,900 ft * Difficulty: Strenuous / Advanced (steep, rugged terrain with rock scrambles) (Trail details to be finalized) ## **WHAT TO BRING** * Sturdy, broken-in hiking boots (a must for this terrain) * Layers and weather-appropriate clothing for higher elevations * At least 2 to 3 liters of water * A packed trail lunch and high-energy snacks * Hat, gloves, and a warm layer (summits run cold and windy in late October) * Trekking poles (recommended) ## **IMPORTANT NOTES** * This is an advanced hike intended for experienced hikers in good physical condition. Prior experience with long, strenuous climbs and scrambling is strongly recommended. * Our adventures are full-day experiences. We do not recommend scheduling other activities that day, as return times can vary. * Unsafe or unsuitable attire and footwear may result in denied participation for safety reasons. Proper hiking boots are required. * If you have any medical conditions or injuries that might prevent you from safely completing a strenuous hike, please consult your physician before signing up. * A signed waiver is required to join the trip. Come ready to challenge yourself, chase the views, and stand on top of the Catskills at the height of fall.

REVERSE Saunter Stretch Series - Stretch #2 (Day 2)

Over three consecutive days, Tuesday through Thursday, we'll walk the iconic 32-mile Great Saunter path in reverse (counterclockwise), circumnavigating Manhattan Island up the East Side and down the West Side. This is Stretch #2 of the series, approximately 11 miles and about 5 hours at a moderate pace. Because we are walking the route in reverse order, the next and final walk will be Stretch #1 on Thursday, October 15. On Wednesday, we begin at 125th Street and Park Avenue and walk around the northern tip of Manhattan to the West Side. Join us for all or part of the walk; there will be drop-out points throughout the route. Meet inside the Harlem-125th Street Metro-North station (125th Street and Park Avenue) at 10:00 a.m. for a prompt 10:15 a.m. departure. We'll walk along the Harlem River to Inwood Hill Park, where we will break for lunch (restrooms will be available) before heading south to the Little Red Lighthouse, then through Fort Washington Park to Riverbank State Park. The walk ends at W. 145th Street and Broadway, at the #1 train subway station. Bring: water, sunscreen, a hat, snacks, and lunch Leaders: Laura, 917-658-6779; Brigitte, 646-651-3911, on day of walk only. **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 11 miles of your total.**