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Challenging Hikes New York

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 LABOR Day 11:30 am Forest Park Hike.

LABOR Day 11:30 am Forest Park Hike.

Mon, Sep 7, 3:30 PM
From Kew Gardens Hiking (Home of the Happy Hikers)
4.9

FROM WALLENBERG SQUARE !!! Werner or Jerry will lead this hike. Today is Werner's birthday. Wish him a happy day! \*\*\* CHECK HERE BEFORE GOING \*\*\* RAIN Will CANCEL HIKE.\*\* Meet time is 11:30AM, hike start is 11:45AM. 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. We will start at 11:30 for this event RAIN WILL CANCEL EVENT!!!!! 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.

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29 attendees
Farewell to Summer Hike at Gertrude's Nose

Farewell to Summer Hike at Gertrude's Nose

Sat, Sep 19, 11:00 AM
From Fellowship of NYC Slothians and Tortoises

It's the last weekend of the summer of '26. Let's take a leisurely hike to Gertrude's Nose at Minnewaska State Park Preserve reachable on Trailways bus out of the Port Authority Bus Terminal going to New Paltz. **NOTE: this is a LEISURELY SLOW PACED PEER-LED hike. You don't have to be an athlete to do this hike. We will not leave you behind HOWEVER you MUST BE ABLE to complete the hike with no issues. There is a 1,200 feet elevation change and some rock scrambling and uneven trails. Your reward will be the most spectacular sceneries you will ever laid your eyes on.** **TRAIL MAP:** https://www.alltrails.com/trail/us/new-york/gertrude-s-nose-via-lake-minnewaska-and-millbrook-mountain-carriage-rd **GETTING THERE:** We're taking the **Trailway bus from Port Authority Bus Terminal.** The 7AM bus arrives in New Paltz by 8:35AM. One-way ticket is $25.00 (depends on how early you buy the ticket). Ticket can be purchased in advance at this link: **[https://trailways.com/](https://trailways.com/)** From the Trailways bus station in New Paltz, we'll then pick up the FREE Ulster County **[Nature Bus](https://ucat.ulstercountyny.gov/routes/nature-bus/)** that will drop us off at the Lake Minnewaska Visitor's Center where we will begin our hike. **Drivers**: you can meet us at the Visitor's Center at 9:30am. Do your own research on directions and parking situation. **PACE**: Hiking pace will be **LEISURELY AND NO ONE WILL BE LEFT BEHIND**. During hike we'll have lunch, water and snack breaks as needed; as well as taking time to savor the sights and sounds of nature, take photos, hug some trees, and most importantly, socialize with your fellow hikers. **NO FAST HIKERS!** **TOTAL MILEAGE**: up to about 7 to 8 MILES **DURATION**: We will be out for the entire day. But you can leave on your own at any time. We won't judge. Much. **AFTER HIKE,** we'll allot some time to explore New Paltz and grab some local bites and drinks before heading home. **RETURN BUS:** 6PM bus back to NYC. **WEATHER**: Rain, extreme heat and humidity cancels! ***LIABILITY WAIVER: come prepared. Participate at your own risks.*** ***Hold no one liable etc etc.***

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1 attendee
The Easiest Catskills Hike

The Easiest Catskills Hike

Sun, Sep 6, 1:00 PM
From Metrotrails: NJ, PA, NY Metropolitan Area Hiking and More!
4.9

Join us for this point to point hike in the southern Catskills, featuring some new trail near the beginning, as well as the former Ulster and Delaware Railroad. We had done a hike years ago, but it has been made into an official trail, so we'll check it out once. Majority of this will be very easy and only gently rolling near the end. Distance is 16 miles. The route will also feature some weaving trails along some creek, a tower, visitor center, and a little bit of back road. If needed, contact me at 908 343 8374

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14 attendees
Harriman Hike from Tuxedo

Harriman Hike from Tuxedo

Sat, Sep 12, 12:45 PM
From Gay Men's Hiking Group
4.9

Let's hike Harriman. It's a less crowded, more wild park. We'll do approximately 8 miles over some hills, rocky outcrops and past a lake. We'll start at Tuxedo train station, making our way to Parker Cabin Mountain, Lake Skenoto and back to Tuxedo. Newbies are welcome but YOU NEED TO BE AEROBICALLY FIT, an experienced hiker or jogger. The trails are rocky and it's a long day of hiking. **TRAIN FROM NYC**: Arrive at Penn Station around 8:35am. We’ll meet inside Penn Station, at the bottom of the escalators at the 7th Ave and 32nd Street entrance. NJTransit ticket booths are right there. We're catching the 8:53 NJCL train #7229. Get out at SECAUCUS then transfer to the 9:30 MNBNP #71 train toward Port Jervis. We'll arrive in Tuxedo at 10:30am. Return trains are 4:20pm and 6:44pm. **TRAIN FROM HOBOKEN:** This is easier for Jersey guys and faster too. At Hoboken Terminal catch the 9:20am MNBNP train #71 toward PORT JERVIS. The NYC guys will board this train in Secaucus. We all get off in Tuxedo at 10:30am. **DRIVERS:** This hike starts and ends in the same place. We'll meet you at Tuxedo train station at 10:30am. There's parking lot a few blocks from the station, but please meet us at the train station. Check the signs and make sure it’s legal to park here. I don’t drive, so I don’t know the rules. Here's the Google pin for the lot [https://maps.app.goo.gl/cBLZKbuDHJthENyq6](https://maps.app.goo.gl/cBLZKbuDHJthENyq6) **FOOD:** Bring plenty of water (2 liters recommended), a hearty lunch and a snacks. There’s two restaurants in Tuxedo for after the hike. **GEAR:** Hiking boots or trail runners. Bring a rain jacket just in case. Bug spray to keep the ticks away. Bring trekking poles if like those. **ALLTRAILS:** Here's a link to the AllTrails map. [https://www.alltrails.com/explore/custom-routes/tuxedo-parker-cabin-skenoto-237ece2](https://www.alltrails.com/explore/custom-routes/tuxedo-parker-cabin-skenoto-237ece2) It's a very useful hiking app I suggest you download it, will be a big help if you ever get lost. I'll put a map in the photos section too. Can't wait to see you on the trails! Any questions contact me, 
Bill Wilson

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22 attendees
Sunday Hike: Cats Rock

Sunday Hike: Cats Rock

Sun, Sep 13, 12:45 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/cats-rock-09-13-26/)** **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/)**

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1 attendee
Monday Hike: Rockwood Hall

Monday Hike: Rockwood Hall

Mon, Sep 7, 1:00 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/rockwood-hall-09-07-26/)** **EXPLORE MORE ADVENTURES HERE ►** **[Upcoming Events](https://outyork.com/new-york-hiking-tours/)** **Rockwood Hall** Join us for a relaxing hike along the Hudson River, featuring beautiful scenery and panoramic views throughout the journey. We’ll visit **Rockwood Hall**, a historic estate with scenic ruins overlooking the river, then walk part of the famous **Old Croton Aqueduct Trail** before continuing into **Rockefeller State Park Preserve**. There, we’ll stop for a peaceful lunch break surrounded by nature. Pack your favorite sandwich and drink, we will have a snack break on the trail. **We’ll end the day at a local ice cream shop** to cool off, relax, and enjoy great conversations together. *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/evening-hike-093f65e--118?u=i&sh=ypq48e) * Difficulty: Challenging. The perceived difficulty may increase if you are a beginner hiker or not physically active. * Elevation Gain: 1,929 ft (588 mt) * Highest Elevation: 1,601 ft (488 mt) * Lowest Elevation: 229 ft (70 mt) * Distance: 6.6 mi (10.60 km) – The distance walk from the train station to the trailhead is 1.8 mi (3 km). This distance is not considered in the hike information. There is a free shuttle, if we ride we won’t walk this distance. * Hiking Time: 6 hr. 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/)**

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1 attendee
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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.