Skip to content

Challenging Hikes New York

Your next hiking adventure starts here

October Hike 🍁

October Hike 🍁

Sat, Oct 31, 1:00 PM
From Jersey City/NYC Hiking & Outdoors
4.9

**Hello! We are planning a hiking trip on October 31st. This is a carpool only hike so let me know if you are driving or if you need a ride. The plan is to meet up at ~9AM and drive to the location. Please reach out if you have questions!** **Trail: TBD** **Note: To pay for the costs of Meetup, there is a $5 fee, waived for drivers who are helping out with rides. I will post my Venmo/ Cash App/ Zelle handle in the comments.**

  • Photo of the user
  • Photo of the user
  • Photo of the user
13 attendees
 Halloween Oct31st ForestPkTwilight Hike

Halloween Oct31st ForestPkTwilight Hike

Sat, Oct 31, 10:00 PM
From Kew Gardens Hiking (Home of the Happy Hikers)
4.9

\*\*\*NO BATHROOMS AVAILABLE\*\*\*PLAN AHEAD\*\*\* \*\*\*COSTUMES OPTIONAL\*\*\* \*\*\* Rainy weather may cancel hike Meet time is 6:PM, hike start is 6:15PM. Duration is about 90 minutes + 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 3 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.

  • Photo of the user
  • Photo of the user
  • Photo of the user
4 attendees

Hike the Greenbelt 🌳🌳

Thu, Oct 29, 7:30 PM
From Staten Island Hiking Meetup
4.8
3 attendees
Last Foliage Hike of the Season [9 miles, Train Access]

Last Foliage Hike of the Season [9 miles, Train Access]

Sun, Nov 8, 3:30 PM
From NYC Hiking And Nature Meetup
4.8

Come join me for the last (probably) foliage hike of the season! We'll do a loop past two lakes and over several great view points. Contact [Andre](http://www.meetup.com/New-York-City-Hiking/members/1650420) with any questions about this meetup. **Event guidelines:** * **This is a social event for hikers, not a guided hike**. We plan to stay together as a group, but everyone needs to be a self-sufficient hiker with adequate skills, equipment, and contingency plans to hike alone with a map or offline-GPS app (and the knowledge to use them) just in case. * **If you are not comfortable hiking** **self-sufficiently** **or are not experienced enough to judge the skill and physical requirements in the route description**, check out the [Appalachian Mountain Club’s](https://www.outdoors.org/) hikes or one of the many professional guides operating in the area. \*\*\* **Standard day-hiking gear:** * Hiking footwear (boots or trail shoes), non-cotton clothing, sunscreen, bug spray, sunhat, sunglasses. ([Permethrin insecticide](https://amzn.to/3XNcflS) treatment against ticks is great.) * Warm layers, including a winter hat and gloves in colder weather. Rain gear and an extra warm layer just in case. * Lunch, Snacks, and 2nd breakfast. 2 liters/ 2 quarts of water minimum, 3 liters for a hot day. Electrolytes for hot days, hot drinks for cold days. * **GPS app with offline maps** & battery pack: **Avenza Maps App** is free and there is a [free Harriman map in the in-app store](https://store.avenza.com/products/harriman-state-park-trail-map-new-york-state-parks-map?queryID=undefined&objectID=36438857941148). **CalTopo** ($20/yr) is an excellent general purpose GPS program. **Mapy** **App** has basic offline trail maps that are adequate. * **Map & Compass**: [NYNJTC Harriman-Bear Mountain Trails](https://amzn.to/422cHxd) or [National Geographic Harriman](https://amzn.to/3MOsk7d) *** **General FAQ:** * No dogs allowed, sorry * No guests beyond the RSVP guest limit and no one under 18 allowed * Hikes are generally rescheduled for thunderstorms, heat index >95f, or AQI >80 \*\*\* **Route Info:** * **The Stats:** About 10.5 miles, depending on conditions, with 1.5k' elevation gain at a moving pace of 2 mph. * **Track:** [Sebago-Skemonto-Claudius Loop](https://www.gaiagps.com/map/?loc=13.3/-74.1436/41.2006&pubLink=KhOL136qZzAYzSiYYCKkgmTW&routeId=ca062906-b224-44a4-8297-1af5195af48e) (If you use AllTrails, you'll have to find a matching route or routes yourself.) * **For Your Contingency Planning:** Shorter routes and bailout points are available. Cell service is generally available but can be spotty. In terms of a navigation & route finding, these are Blazed Trails. \*\*\* **Logistics:** * **Meeting Location:** Meet at 10:30am at the Tuxedo commuter parking lot off East Village Road ([Google Maps](https://goo.gl/maps/aoABudbFJkjAKF926)). (Use the address 2 Powerhouse Ln, Tuxedo Park, NY 10987.) * Andre's Cell: â€Ș(720) 263-7347‬; texts preferred. * **Public Transit:** Take the 9:14 am NJ Transit train from Penn Station to Tuxedo Station, arriving at 10:29 am. The station is just around the corner from the parking lot where we are meeting. Catching the 4:20 train back should work, but that might require cutting the hike short. Alternatively, return on the 6:44 pm train, or one of the hourly trains from Suffern via Uber. * **Car Pooling:** Please use the comment section to organize carpooling, especially if you are driving from the city. Passengers should chip in for gas and tolls (usually about $10-$15). ***

  • Photo of the user
  • Photo of the user
  • Photo of the user
30 attendees
Halloween Hike to Raven Rocks, with transportation

Halloween Hike to Raven Rocks, with transportation

Sat, Oct 31, 11:15 AM
From Adventure Untamed
4.7

**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/halloween-hike-to-raven-rocks-2/). **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 guide are included in the cost of the trip. All you have to do is show up!** Celebrate Halloween with a Spooktacular hike from Adventure Untamed. First, we are off to Raven Rocks! Raven Rocks is the most remote area of the Rockefeller State Park Preserve, so you know we are in for a treat! This hike has a little bit of everything: pastures, a brook, lakes, old growth forest, and so much natural beauty. We will traverse both hiking and gravel paths and climb up to a beautiful rock outcropping on top of a cliff. After the hike, we are celebrating Halloween with the [Knickerbocker Tour](https://www.showclix.com/tickets/the-original-knickerbocker-tour-2025) that will take us to a cemetery at Sleepy Hollow where we will learn more about *The Legend of Sleepy Hollow*! It’s going to be a fantastic adventure! Come celebrate Halloween with us! This is an **INTERMEDIATE-** level hike, suitable for **ACTIVE-level hikers**. Costumes not required, but strongly encouraged :). Best costume wins a free AU day hike! Make sure your costume is comfortable enough to hike! **What’s included:** * NY State Licensed and Wilderness First Responder Certified Guide * Transportation to and from NYC (if you would like to meet us at the trailhead, please email [info@adventureuntamed.com](mailto:info@adventureuntamed.com) for a discount) * Tickets to the Knickerbocker Tour [Cancellation Policies](https://www.adventureuntamed.com/info/?tab=2) **Wear** * Hiking boots * Weather-appropriate, moisture-wicking, athletic clothing (**no cotton**) * Wool or synthetic socks (**no cotton**) * Sun hat * Sunglasses **Pack** * Windproof/waterproof top and bottom layers that can fit over all other layers * Lunch * Ample Snacks * At least two (2) liters of water * Backpack * Sunscreen * Extra layers to adjust for changing weather conditions * Extra pair of wool socks * Trekking poles (optional) * A change of clothes for the ride back (optional) **Level:** INTERMEDIATE- (https://www.adventureuntamed.com/info/?tab=1) **Mileage:** 5.5 miles **Elevation Gain:** 600 feet **Group Size:** 2 - 14 adventurers

  • Photo of the user
1 attendee
Sunday Hike: Sunset @ Breakneck Ridge

Sunday Hike: Sunset @ Breakneck Ridge

Sun, Nov 1, 5:25 PM
From Outyork: Adventures in New York and Beyond
4.8

**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 â–ș [HERE](https://outyork.com/new-york-hiking-tours/sunset-breakneck-ridge-11-07-26/)** **EXPLORE MORE ADVENTURES HERE â–ș** **[Upcoming Events](https://outyork.com/new-york-hiking-tours/)** **Breakneck Ridge** Take on one of the most iconic hikes in New York at Breakneck Ridge. This challenging trail features steep climbs and rugged terrain, perfect for adventure seekers. **Conquer the summit at golden hour and enjoy a stunning Hudson River sunset**—a truly unforgettable New York hiking experience. **Pack your headlamp and wear your best hiking shoes for this adventure!** Pack your favorite sandwich and drink, we’ll take a snack break while enjoying the sunset. *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.* đŸ—ș 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:** Challenging. 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 â–ș** **[Upcoming Events](https://outyork.com/new-york-hiking-tours/)**

  • Photo of the user
1 attendee
430kMonthly events
calendar icon
60mMembers
people1 icon
4.5App store rating
appStore icon
200kGroups
people2 icon

Frequently asked questions

Meetup is used to find and join local groups, participate in events both in-person and online, and connect with people who share similar interests in a community setting.

To find hikes in New York, search for hiking groups in the area on Meetup. You can filter events by location to explore challenging trails shared by outdoor enthusiasts.

Absolutely, you can join as many hiking groups as you like. Meetup provides flexibility to engage with different groups that match your interests and fit your schedule.

Yes, many Meetup groups organize outdoor events, including hikes, in areas like New York. Join a group to receive notifications about upcoming outdoor adventures.

To RSVP, simply find the hiking event you're interested in on Meetup, open the event page, and click 'RSVP' to confirm your attendance and receive event updates.

Yes, maintain specific searches for challenging or advanced adventure hiking groups on Meetup. Many communities cater to seasoned hikers looking for a challenge.

Joining Meetup as a participant is generally free, though some events or groups might ask for a nominal fee to cover costs associated with organizing events.

If a hike is canceled, you should receive a notification from the group organizer. Cancellations and updates are typically communicated through the Meetup platform.

Not all trails are difficult; Meetup caters to a wide variety of skill levels. You'll find diverse options from easy walks to challenging climbs to suit your hiking preference.

Group hikes are organized by members through Meetup, where details such as location, time, and difficulty level are provided, and participants join to hike together.

Meetup helps you connect with groups, but the availability of specific hiking groups depends on your location and the hiking community's current offerings.

If an ideal hiking group doesn't exist, you can create one yourself on Meetup. This allows you to set details according to your preferences and interests.

Meetup focuses on group events rather than one-on-one matches, but it can still be a great way to meet people with similar hiking interests who you might later form one-on-one connections with.

Hiking events are typically in-person to fully enjoy the activity, but some groups might hold virtual events for planning or discussing outdoor topics.

The frequency of hiking events varies by group and organizer activity. Exploring several groups increases chances to find numerous events to fit your schedule.