Challenging Hikes New York

Early Morning Hike 😊

Our First Hike at Mohonk Preserve

**Welcome Slothians and Tortoises!** **For our very first Meetup ...** let's get outdoors and take a hike at **[Mohonk Preserve](https://www.mohonkpreserve.org/who-we-are/)** reachable on Trailways bus out of the Port Authority Bus Terminal going to New Paltz. **AGENDA:** We'll hike the Testamonial Gateway Trail, connecting to Duck Pond trail, then River-to-Ridge trail that will take us back to New Paltz. **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 $26.00 (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 **[Nature Bus](https://ucat.ulstercountyny.gov/routes/nature-bus/)** at 8:45am that will drop us off at the Mohonk Testimonial Gateway at 8:55am. **Drivers**: you can meet us at the Testimonial Gateway parking lot at 9am. 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, 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:** There is a 6PM bus back to NYC, as well as an 8PM bus. It's a long holiday weekend - enjoy the last vestige of long summer hours by staying a bit later and exploring New Paltz before taking the 8PM bus home. **WEATHER**: as bus ticket is non-refundable, this meetup is rain or shine! ***LIABILITY WAIVER: come prepared. Participate at your own risks.*** ***Hold no one liable etc etc.***

Catskills Adventure Challenge: Rochester Hollow

**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/catskills-adventure-challenge-rochester-hollow/). **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!** The Catskills Center has put together a series of hikes as part of the Catskills Adventure Challenge. The Challenge consists of a series of hikes designed to introduce hikers to the region. Adventure Untamed is taking on the challenge! If you complete six of the eight hikes that are part of the Catskills Adventure Challenge, you can earn a patch from the [Catskills Adventure Center](https://www.catskillcenter.org/adventurechallenge?mc_cid=8b2b6a6c7f&mc_eid=700fe10aae). Adventure Untamed is planning to do all eight hikes in 2026. Next up – Rochester Hollow! Rochester Hollow is a plot of land near the Big Indian Mountain. It’s a series of three connecting trails and a quintessential hike in through the woods. The word that repeatedly comes up to describe this trail is ‘peaceful.’ The woods, remnants of old stone walls, wild life, and a walk through the woods. **What’s included**: * NY State Licensed and Wilderness First Responder Certified Guide * Transportation to and from NYC * Hike from the Catskill Adventure Challenge [Cancellation Policies](https://www.adventureuntamed.com/info/?tab=2) **Wear** * Hiking boots (**required**) * Weather-appropriate, moisture-wicking, athletic clothing (**no cotton**) * Wool or synthetic socks (**no cotton**) * Waterproof gloves * Warm hat * Buff * Sun hat * Sunglasses **Pack** * Fleece / mid layer * Windproof/waterproof top and bottom layers that can fit over all other layers * Lunch * Ample Snacks * At least three (3) liters of water * Backpack * Sunscreen * Fully waterproof top and bottom layers that can be worn over all other layers * Extra layers to adjust for changing weather conditions * Extra pair of wool socks * Headlamp * Trekking poles (optional) * A change of clothes for the ride back (optional) **Level:** ACTIVE (https://www.adventureuntamed.com/info/?tab=1) **Mileage:** 4.8 miles **Elevation Gain:** 859 feet **Group Size:** 2 - 14 adventurers

The Easiest Catskills Hike

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

Monday Hike: Rockwood Hall

**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/)**

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-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/)**

Details Coming Soon: Annapurna Circuit Trek (High Altitude/Strenuous)

Sunday Hike: Anthony's Nose

**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/anthonys-nose-09-06-26/)** **EXPLORE MORE ADVENTURES ►** **[Upcoming Events](https://outyork.com/new-york-hiking-tours/)** Discover the OutYork experience by joining us for an unforgettable moderate hike to Anthony’s Nose, a must-visit trail in New York’s Hudson Valley. Hike through picturesque woodlands before reaching the summit, where you’ll be greeted with breathtaking views of the Hudson River and surrounding mountains. This scenic escape is perfect for those looking to reconnect with nature, breathe fresh air, and leave the city behind. Whether you're an experienced hiker or just starting out, Anthony’s Nose offers the ideal adventure for nature lovers and outdoor enthusiasts alike. Pack your favorite sandwich and drink, we will have a snack break on the trail. Don’t miss out on this exciting journey! *We are getting away from the city to forget about timing, enjoy nature and socialize. If you're looking to make new outdoorsy friends, you've found the perfect place. But if you're seeking a fast-paced group, this might not be the right fit.* 🗺️ About the Hike * **Small Group Experience:** 2 - 15 OutYorkers. * **Hike Route:** **[AllTrail Map](https://www.alltrails.com/es/explore/recording/afternoon-hike-at-rockwood-hall-pocantico-river-and-old-croton-aqueduct-loop-7f16109?u=i&sh=ypq48e)** * **Difficulty:** Moderate. **The perceived difficulty may increase if you are a beginner hiker or not physically active.** * **Hiker Skills:** Active person with basic fitness. Comfortable with long walks and some uphill sections. * **Elevation Gain:** 1,195 ft (364 mt) * **Highest Elevation:** 892 ft (272 mt) * **Lowest Elevation:** 10 ft (3 mts) * **Distance:** 6.44 mi (10.36 Km) – This includes the walk from the train station to the trailhead. * **Hiking Time:** 3h. 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 ►** **[Upcoming Events](https://outyork.com/new-york-hiking-tours/)**

Yosemite Half Dome Backpacking

Hit your bucket list with all the feels on this women’s guided hiking and backpacking weekend! During your Yosemite Half Dome Hike adventure, tour Yosemite National Park as you climb the famous cables of Half Dome with ladies who do their own stunts. Live out every last one of those John Muir nature quotes in the backcountry of Yosemite National Park. Mountains calling? Check. Between two pines? Check. Walk with nature? Double-check. **GUIDED BACKPACKING IN YOSEMITE NATIONAL PARK BACKCOUNTRY** Romp through the backcountry on a demanding, yet epic backpacking trip. Meet your new woman crushes in the Yosemite Valley as the landscape gives way to mountains, waterfalls, and a piney perfume that’ll make Yankee Candle totally jelly. Mother Nature swiped ALL THE WAY right. Leave the phone on airplane mode to immerse yourself in stunning national park backcountry over the course of four epic days. Climb steep, challenging trails to look down upon the Valley with a panoramic view that includes Mt. Starr King, Half Dome, Nevada Falls, Illilouette Falls, and plenty of ant-sized tourists with tiny selfie sticks. **HALF DOME: HIKING TO THE TOP** Fuel up for the real MVP—the famous cables of Half Dome! Blast that hiker booty (and bring plenty of water) while ascending 500 feet up a .5 mile of steps carved into the rock. Then, the real fun begins. It’s a 400-foot gain up the top of Half Dome with some points at 70%+ grades. Pace your footwork on wooden slabs spaced out on the climb as you get the upper body workout of a lifetime. Worth it? HELL YES! **BACKPACKING EQUIPMENT PROVIDED** Don’t have backpacking equipment, but can Beastmaster the stairs? Perfect. Explorer Chick has you covered with: * a backpack * sleeping bag * sleeping pad * shared tent All you need to do is show up for this Yosemite Half Dome Hike to backpack like a boss and get that National Parks bucket list checked. **See the website for full itinerary, details and to book.** [https://explorerchick.com/adventures/yosemite-half-dome-hike-backpacking](https://explorerchick.com/adventures/yosemite-half-dome-hike-backpacking/) **Say Hello 👋** **💻** Website: [https://explorerchick.com/](https://explorerchick.com/) 📧 Email: hello@explorerchick.com 📸 Instagram: [https://www.instagram.com/explorerchickadventureco/](https://www.instagram.com/explorerchickadventureco/) ❤️ Facebook: [https://www.facebook.com/ExplorerChickAdventureCo/](https://www.facebook.com/ExplorerChickAdventureCo/) 👯‍♀️ Facebook Group: [https://www.facebook.com/groups/weareexplorerchick](https://www.facebook.com/groups/weareexplorerchick) 🎥 TikTok: [https://www.tiktok.com/@explorerchick](https://www.tiktok.com/@explorerchick)

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-09-03-26/)** **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/)**

Unlock the Secrets of Mostly Northern Central Park, Labor Day Weekend

IF THIS IS YOUR FIRST EVENT WITH US, IMMEDIATELY AFTER YOU RSVP WHETHER YOU ARE ON THE WAIT LIST OR NOT, YOU MUST SEND ME YOUR E-MAIL TO MY E-MAIL AS EXPLAINED BELOW. I use capital letters to emphasize stuff not to shout at you! Sometimes I hear people say they know the Park like the back of their hand-and I know they are exaggerating but don’t even know it! WE WILL SEE SOME WATERFALLS. PLEASE DO NOT CLICK ON THE RSVP BUTTON UNTIL YOU HAVE READ THE ENTIRE DESCRIPTION OF THE EVENT VERY CAREFULLY. I just ask that all attendees be considerate with respect to the RSVP process. The wait list for this group does NOT operate in a conventional way. Those on the wait list will NOT be moved to the going list automatically. We are also looking to add a number of First Timers to this event. However, you actually need to read the description of the event carefully. FIRST TIMERS: IF YOU HAVE NEVER ATTENDED AN EVENT BEFORE WITH THE GROUP, I AM ASKING FOR YOUR HELP AND COOPERATION. I AM REQUIRING THAT YOU SEND ME AN E-MAIL 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. (NO GUESTS UNLESS YOU HAVE ATTENDED AN EVENT BEFORE WITH THIS GROUP-Your guest can always sign up just as you did.) I am going to require that everyone who attends this event make a monetary contribution but the amount of that contribution is up to you. Meetup charges an Organizer like me each month - it's not a fortune although the cost was raised substantially-but most importantly, I spend much time and effort planning and preparing for an event. You can contribute whatever you want at the BEGINNING of an event. If you don't think I have earned your contribution, I will give you your money back-no questions asked. (Last year, there was no cost for the majority of events this group conducted.) PLEASE ALSO READ "WHAT WE'RE ABOUT" ON THIS MEETUP'S HOME PAGE INCLUDING THE WAIVER OF LIABILITY BEFORE YOU RSVP. MEETING DETAILS WILL BE SENT BY E-MAIL TO THOSE WHO RSVP NO LATER THAN THE EVENING BEFORE THE TOUR AND PROBABLY SOONER. 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. YOU CAN EVEN CUSTOMIZE YOUR SETTINGS TO SELECT THOSE GROUPS YOU WANT TO RECEIVE MESSAGES FROM. My intent for this event is that it be a fun, ambitious and interesting, fast paced hiking tour of about 7 miles where we will cover what existed BEFORE Central Park was even built, the history of the Park, and it's design features. We will also see the new Davis Center area where the Lasker skating rink used to be as well the significant changes to the landscape up north which now conforms more closely to the original design of the Park. I will stop a number of times to very briefly talk about what we are seeing. That means I talk and you listen or make believe you are listening! Over the years this group has conducted numerous tours of Central Park and I have led several tours of Northern and Southern Central Park for the Guides Association of New York City (GANYC). This event will be even better. Much better! We are going to keep things moving as much as possible. On this hiking tour we hope to visit areas such as the Ramble where there will be one short climb, Conservatory Gardens, the Ravine, the Great Hill, the Blockouse and the North Woods where there are waterfalls. Central Park is often considered a work of art and hopefully we can show you why! (Photo by the late and great photographer Sonia Braga) We will probably start in lower/mid Central Park and head north to the tip of the Park. Of course, you can leave any time. We will be zig-zagging quite a bit. Public transportation will be easy to find before and after the event. Registration will be limited to around 20 members or so. We will meet BEFORE 10:15 A.M. and finish around 3:30 P.M. or so NOT far from public transportation at West 96th Street. If you drive, parking is free on Sundays. We plan to start on the east side and finish on the west side-but you can leave any time. THERE WILL BE A BRIEF LUNCH STOP AT SOME POINT. BRING LUNCH/SNACKS AND WATER. WE WON'T STOP ANYWHERE TO BUY FOOD. THIS GROUP NEVER GOES FOOD SHOPPING DURING AN EVENT! IN CASE YOU ARE WONDERING, THERE WILL BE SEVERAL PLANNED BATHROOM STOPS DURING THE EVENT. FINDING GOOD BATHROOMS IS ONE OF THE STRENGTHS OF THIS GROUP. AS ALWAYS, I am also 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 neither does anyone else what you are doing that day if you can’t make it or what you think the weather will be, etc. etc. You may even think you have some deep insights into something or other but I ask you to keep that deepness to yourself. AFTER the event, post as many comments and photos as you like. The comments/questions you post BEFORE an event are almost always annoying and unnecessary and I'm not the only one who believes that. PLEASE RESPECT MY WISHES ON THIS. If the weather forecast is bad, I will post a notice on the day of the hike by 7:00 A.M.

Catskill 3500 Bushwhack - Mount Sherrill

In order to officially secure your spot on this event and to receive the details email of where to exactly park and meet with us you must register on our site by clicking the link below. https://www.trailboundproject.com/service-page/catskill-3500-bushwhack-mount-sherrill?referral=service_list_widget Our events typically fill up at 24 people for guided hikes! You won't see the attendees here on meetup as registrations are on our site but we wanted to let you know that we typically see large outings for all of our events! Mount Sherrill is a 3,550' tall trailless peak and one of the 33 Catskill 3500 peaks that one must climb to become a Catskill 3500 Club member. We will be doing an out-and-back hike with about 6 miles of herd-paths and bushwhacking, ending up with a total of 2,000' of elevation change that takes 5 to 7 hours to complete. We will be following the herd-paths at a leisurely to moderate pace, but we'll have the opportunity to do some true bushwhacking over to the secret school bus, which was once used as an old hunter's camp. Be prepared for sustained off-trail navigation through dense forest, uneven footing, and steep terrain. Expect a physically demanding day with significant elevation gain and slow, deliberate movement. While mileage is moderate, the terrain makes this a full-value mountain day. Throughout the hike, we will focus on: • Map and compass navigation • Terrain assessment and going over route options • Proper footwork on steeper, rougher terrain Sherrill is not about speed or views. It's about precision, discipline, and controlled movement through terrain that is off the beaten path. Join us for a day of fun navigation challenges in beautiful terrain! The parking and hike details are emailed after registration.