Skip to content

Challenging Hikes New York

Your next hiking adventure starts here

Saturday Hike: Sunset @ Breakneck Ridge

Saturday Hike: Sunset @ Breakneck Ridge

Sat, Nov 7, 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 ► [HERE](https://outyork.com/new-york-hiking-tours/sunset-breakneck-ridge-11-07-26/)** **EXPLORE MORE ADVENTURES HERE ►** **[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.* 🗺️ 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 ►** **[Upcoming Events](https://outyork.com/new-york-hiking-tours/)**

  • Photo of the user
1 attendee
7.5 Mile Central Park Hike & Dinner

7.5 Mile Central Park Hike & Dinner

Sun, Nov 8, 5:15 PM
From The New York Afternoon Hiking Meetup
4.7

We'll be meeting at the corner of W 69th St & Central Park West. We'll do a loop around Central Park, then go to a Chinese restaurant that does separate checks for dinner. Meetup.com is malfunctioning and refuses to set any start location within a few blocks of my desired location at 69th & Central Park West. There is no vaccination requirement for this hike, neither for the hike itself nor for the dinner afterward. The restaurant is not announced online as we don't want people skipping the hike and meeting us at the restaurant. This is a hiking meetup, not a dining one. We will be reaching the restaurant around 4:15pm (sunset will be at 4:45pm). Rain cancels. Snow does not. Take any train to Columbus Circle and walk 9 blocks north, or the 1 train to 66th and it's a short walk, or the 2/3 to 72nd and it's a short walk. This event is provided at no financial cost, in exchange for your relinquishing the right to sue the organizers for anything unfortunate that may happen during this outing. By attending this event, you agree to the terms laid out in a lengthy legalese waiver which can be found at **[http://bluejacket7.com/legal/WalkingWaiver.doc](http://bluejacket7.com/legal/WalkingWaiver.doc)** . There is especially a risk that you will get separated from the group and lost, and if that happens the responsibility will be yours.

  • Photo of the user
  • Photo of the user
  • Photo of the user
15 attendees

Let's hike part of the white trail 5 miles 🌳🥾

Mon, Nov 2, 5:30 PM
From Staten Island Hiking Meetup
4.8
6 attendees
The Queens Way-The Possible High Line of Queens, Forest Park and Forest Hills

The Queens Way-The Possible High Line of Queens, Forest Park and Forest Hills

Sun, Nov 15, 3:15 PM
From New York City Hiking Tours
4.9

We would like to add some first timers who actually are serious about joining us. If you have NEVER attended an event before with this group, please send me your e-mail to my e-mail as requested below whether you are on a going list or wait list AFTER CAREFULLY READING THE DESCRIPTION OF THIS EVENT. DO NOT SEND YOUR E-MAIL TO ME THRU A MEETUP MESSAGE. See below. IF YOU HAVE NEVER ATTENDED AN EVENT BEFORE WITH THE GROUP, I AM ASKING FOR YOUR HELP AND COOPERATION AS I PLAN THE EVENT. I AM THEREFORE REQUIRING THAT YOU SEND ME AN E-MAIL AFTER CAREFULLY READING THE DESCRIPTION OF THE EVENT TO [bsb2@att.net](http://bsb2@att.net/) AS SOON AS YOU RSVP, EVEN IF YOU ARE ON THE WAIT LIST, AND PUT YOUR E-MAIL ADDRESS IN THE BODY OF YOUR MESSAGE TO ME. THIS WILL HELP ME COMMUNICATE MORE EFFECTIVELY WITH THOSE WHO RSVP. SOMETIMES MEETUP MESSAGES DO NOT GET DELIVERED FOR A VARIETY OF REASONS. IF YOU CAN'T ABIDE BY THIS SIMPLE REQUEST, YOU ARE GOING TO END UP ON THE NOT GOING LIST. If you think this request is just too much for you to bear, please let me know. I use capital letters to emphasize stuff not to shout at you! WE ARE LOOKING TO ADD SOME FIRST TIMERS. PLEASE READ WHAT I WRITE CAREFULLY. DO NOT RUSH THE RSVP PROCESS. THERE IS NO NEED TO. NO GUESTS FOR FIRST TIMERS. YOUR GUEST CAN SIGN UP AS YOU DID. I consider this a members appreciation event. We will NOT accept any monetary contributions on this one. I want to primarily reward those members who have supported this group in the recent past by attending at least one event and hopefully more with few cancellations. It helps if you are also a member of my other group called NYC Wanderers. See: [https://www.meetup.com/nyc-wanderers/?eventOrigin=your_groups](https://www.meetup.com/nyc-wanderers/?eventOrigin=your_groups) As always, the waitlist for this group does NOT operate in the conventional way. Those on the waitlist will NOT be moved automatically to the going list when a space becomes available. IF APPLICABLE, ALWAYS JOIN THE WAIT LIST WITH LOW PRIORITY WHICH IS FREE. IF THERE IS A WAITLIST, IT APPEARS MEETUP WILL ASK YOU IF YOU WANT TO JOIN MEETUP + BUT IN SMALLER LETTERS AT THE TOP OF THE PAGE YOU CAN CLICK CONTINUE WITH THE FREE PLAN. There is NEVER a need to pay extra to use Meetup's High Priority wait list classification for this group. THIS IS THE ONLY THE THIRD TIME WE ARE DOING THIS PARTICULAR EVENT AND THE SECOND TIME I AM DOING IT. In 2025, I felt this may have been the most unique event we did that year. This event will be a fun, fast paced approximately 6 mile hike. We will begin by walking through a bit of Forest Hills and Forest Hills Gardens where I will provide limited commentary. We will then get a glimpse of where the first section of The Queens Way is hopefully going to be built-IT HAS FUNDING NOW- but we will NOT walk on the abandoned railroad tracks on this first section. (The Queens Way is designed to be a linear park built on an abandoned stretch of rail tracks in Central Queens with some similarity to the High Line but it has NOT been built yet). Then it gets rather gritty as we walk towards what is another section of The Queens Way-no funding to build yet- where we will scramble up a slight incline from some abandoned railroad tracks to get into Forest Park. There we will do a relatively short hike in the Park to finish. MEETING DETAILS WILL BE SENT OUT VIA A MEETUP MESSAGE TO ALL THOSE WHO RSVP NO LATER THAN THE EVENING BEFORE THE EVENT. YOU CAN GET THERE EASILY BY SUBWAY OR THE LONG ISLAND RAILROAD. WE WILL NOT BE ENDING WHERE WE STARTED-2 SHORT SUBWAY STOPS AWAY-ABOUT A LITTLE MORE THAN A MILE- BUT WE WILL FINISH NEAR A MAJOR SUBWAY STATION AND NOT FAR FROM THE LONG ISLAND RAIL ROAD. We will meet a bit BEFORE 10:15 A.M. Be ready to go. WE LEAVE ON TIME. BRING SNACKS AND WATER. THERE IS NO LUNCH BREAK. THIS GROUP NEVER STOPS TO BUY FOOD ON AN EVENT. IF YOU HAVE NOT ALREADY DONE SO, ON YOUR DESKTOP, PLEASE CLICK ON YOUR PROFILE WHICH IS ON THE TOP RIGHT OF THE SITE, THEN CLICK "SETTINGS", THEN CLICK E-MAIL UPDATES" ON THE LEFT. MAKE SURE YOUR E-MAIL UPDATES ARE ON AND WHERE IT SAYS "UPDATES ABOUT YOU”, CHECK MESSAGES BOX. THIS WILL HELP TO INSURE YOU GET MESSAGES FROM ME. I LIKE TO THINK THOSE MESSAGES ARE IMPORTANT. IT LOOKS LIKE YOU CAN CUSTOMIZE YOUR SETTINGS FOR A SPECIFIC GROUP WHICH MAY BE HELPFUL IF YOU BELONG TO MANY MEETUP GROUPS. I am going to ask that people not post any comments or questions prior to the event. You have more than enough information to do this once you get the meeting details. No offense, but I don’t need to know-and probably neither does anyone else- what you are doing that day if you can’t make it or what you think the weather will be. AFTER the event, post as many comments and photos as you like. PLEASE RESPECT MY WISHES ON THIS. We will probably finish by 1:45p.m. and not far from a major subway station. It won't be easy to leave before we finish because of the route we are taking. WE WILL NOT FINISH WHERE WE START. IT WILL BE EASY TO GET TO THE EVENT AND HOME BY SUBWAY. FOR DRIVERS, YOU CAN PARK NEAR THE BEGINNING, THE END OR IN BETWEEN LOCATIONS. SUNDAY PARKING IS FREE. If the weather forecast is really bad, I will post a notice on the day of the hike by 7:00 A.M. If there is no notice, we go. RAIN DATE WILL BE SUNDAY NOVEMBER 22.

  • Photo of the user
  • Photo of the user
  • Photo of the user
28 attendees
Adventure Book Club: The Only Way Is West

Adventure Book Club: The Only Way Is West

Fri, Nov 13, 12:30 AM
From New York Backpackers
4.8

The Only Way Is West: A Thru-Hiking Adventure by Bradley Chermside What does it take to walk hundreds of miles across northern Spain? Blisters, questionable decisions, beautiful landscapes, unexpected friendships, a sense of humor, and a whole lot of determination. This time, we’re reading The Only Way Is West, a travel memoir about hiking the Camino de Santiago. Join us as we explore the challenges, surprises, and unforgettable moments that come with taking on an epic journey on foot. Let’s Talk Adventure! This isn’t just about the book. We want to hear about your adventures, too! Have you tackled a multi-day trek, hiked a legendary trail, or found yourself somewhere spectacular after a long day on your feet? Or maybe you’ve got a bucket-list hike you’ve been dreaming about for years. Bring your stories! We’ll share epic hiking experiences, ambitious trekking plans, and the adventures we’d love to take someday. No need to be an experienced thru-hiker. Just bring your curiosity, your love of adventure, and your enthusiasm for a good book. **Tentative schedule** 7:30 - 8pm Socialize, get comfy 8 - 9pm Book Chat 9pm + Food, drinks either at the venue or somewhere close by 📚💙 Epic Stories | Real Adventures

  • Photo of the user
  • Photo of the user
  • Photo of the user
13 attendees
Hiking the length of Manhattan from the North to South - 20 mile walk

Hiking the length of Manhattan from the North to South - 20 mile walk

Sat, Nov 7, 2:00 PM
From New York Backpackers
4.8

Let's walk or I guess "hike" the entire length of Manhattan from North to South. We will meet at the at 0900 at Mon Amour Coffee and Wine in Kingsbridge in The Bronx and walk all the way down to Staten Island ferry. We did this last year and it was such a blast so why not do it again! It is the day before the NYC marathon so perfect time do our own marathon at a slow poke pace. We will make stops for breakfast, lunch, beer or wine and dinner along the way. You can join in and out over the day but it is better if you come for the whole thing. Schedule that I am going to post is a rough one and we might be there earlier or later depending on our walking speed, etc. I will set up a WhatsApp chat the day before with live location if people want to catch up to us by subway or Citi bike. I picked a coffee shop in Kingsbridge so we could walk down to Marble Hill and start from the north border of Manhattan. Kingsbridge used to be an actual bridge that separated The Bronx from Manhattan until the Harlem River was landfilled and now it is just the neighborhood where the northern end of the bridge used to lie. The River itself was too shallow and narrow for boats so a canal was dug out on the southern end of Marble Hill turning Marble Hill briefly into an island until the river was landfilled on the north side. Marble Hill then became attached to The Bronx and became a Manhattan enclave in The Bronx. We will meet at Mon Amour Coffee and Wine at 0900 and start our walk, saunter or hike from there. https://maps.app.goo.gl/WTaRNkEZtiZUhtM77 **Rough schedule:** 9h00 Mon Amour Coffe and Wine next to the 238th St Station in The Bronx 9h45 Stop at Inwood Farms for brunch 11h00 Leave Inwood Farm 11h30 The Cloisters 14h00 Central Park North and Adam Clayton Powell 16h00 Playa Betty's for late lunch or early dinner 17h30 Leave Playa Betty's 19h30 Stop at Brass Monkey for drinks 20h30 Leave Brass Monkey 21h30 Arrive at the Staten Island Ferry 22h00 Dinner at Hey Thai on John St This is roughly a 20 mile walk. Bring a water bottle. Restaurants we stop at and bars will be happy to refill your bottle for you. Bring comfortable shoes. If you want bring two pairs of shoes and socks. Some people find it easier on their feet to switch shoes and socks halfway through. If we end up with a big crowd I would prefer to give priority to those who can commit to doing the whole thing. Last year we finished with 5 out of 20 while a group did the same thing and everyone in their group finished. Commitment would be awesome!!!

  • Photo of the user
  • Photo of the user
  • Photo of the user
45 attendees
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.