Outsiders NY

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Ready to level up your hiking game? Join us for a serious challenge in the heart of the Catskills as we take on Indian Head Mountain — one of the region’s most rugged and rewarding trails.
This isn’t your average walk in the woods. Expect steep climbs, technical rock scrambles, and sustained elevation that’ll push your endurance and test your grit. This 7+ mile loop is for experienced hikers who thrive on intensity and love the satisfaction of earning every single view.
And the views? Absolutely worth it. Picture dramatic cliffs, sweeping Hudson Valley vistas, and quiet forest moments that feel a world away from NYC.
We’ll kick off the day early at The Standard Biergarten in Meatpacking, tackle the trail, and celebrate with food and drinks after the hike.

REGISTER HERE TO ATTEND https://joinoutsiders.com/events

EVENT TIMELINE:
📍 8:00 AM – Meet at The Standard Biergarten (Meatpacking)
🚌 8:30 AM – Depart NYC
🥾 10:30 AM – Arrive at trailhead and begin hike
🥪 1:00 PM – Snack break on the ridgeline
🏁 3:30 PM – Conclude hike and head to post-hike hang
🚌 6:00 PM – Depart back to NYC
Times are approximate and subject to group pace and trail conditions.

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WHAT’S INCLUDED IN YOUR TICKET:
✅ Roundtrip transportation from NYC
✅ Guided hike led by experienced trail leaders
✅ Water provided by Spindrift
✅ Beverages on the ride home,

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HIKE DETAILS:
🥵 Difficulty: Hard (Advanced-level only)
📏 Distance: ~7 miles
📈 Elevation Gain: ~1,600 ft+
🧗‍♂️ Terrain: Rock scrambles, steep inclines, exposed viewpoints

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WHAT TO BRING:

• Sturdy hiking boots (no sneakers!)
• At least 2L of water
• High-energy snacks or lunch
• Weather-appropriate layers
• Your strongest legs and best attitude

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This trail is tough, remote, and incredibly rewarding — if you're looking for a real mountain challenge, Indian Head is calling.
Grab your spot and let’s go show this mountain who's boss. 🏔️🔥💪

REGISTER HERE TO ATTEND https://joinoutsiders.com/events

Escape to the countryside and enjoy a relaxing trek with your new furry BFFs – llamas and alpacas. Before you know it, you'll be hiking alongside these adorable, Instagram-worthy creatures through scenic trails that’ll make you forget the concrete jungle.
This isn’t your typical nature walk. Picture it: rolling hills, fresh air, and the cutest hiking partners ever. It’s the perfect mix of adventure and zen. Whether you're in it for the animal snuggles or the panoramic views, you’ll walk away with some unforgettable memories (and amazing pics, of course).
Pack your comfiest sneakers, grab a water bottle, and bring your crew. You’ll want to experience this one together! After our adventure with the Llamas & Alpaca's we'll make our way to a brewery or winery before heading back to NYC.

REGISTER HERE TO ATTEND https://joinoutsiders.com/events

EVENT DETAILS:

• 10:00 AM – Meet at The Standard Biergarten
• 10:30 AM – Depart
• 12:45 PM – Arrive at the farm entrance
• 3:15 PM – Finish the Llama and Alpaca Hike & head to a local brewery or winery
• 5:30 PM - Depart back to NYC

(All times are approximate and subject to change based on traffic and group pace)
What's included in your ticket:

• Transportation
• Guided Hike
• Farm access
• Llama and Alpaca Hike
• Beverages on the ride back home

If you are not dressed in weather-appropriate gear or if your attire is deemed unsuitable for the activity, we have the right to turn you down for the safety of the group and yourself.

If you have any medical conditions or injuries that might prevent you from completing the trip, please consult your physician to confirm your ability to partake in the activities safely.

REGISTER HERE TO ATTEND https://joinoutsiders.com/events

Get ready for a spine-tingling hike through history — and maybe even a few ghost stories. This Halloween weekend, we’re heading deep into the Catskills for a one-of-a-kind adventure to the skeletal remains of the Overlook Mountain House, an abandoned hotel from the 1800s that now stands as a haunting ruin along one of the region’s most iconic trails.
This moderate 5-mile hike winds through beautiful forested paths, past eerie stone foundations, and up to sweeping mountain-top views that overlook the Hudson Valley. We'll also pass a fire tower (for those brave enough to climb) and possibly spot vultures circling overhead — no joke.
Throw on a costume (seriously, it makes it more fun), pack some snacks, and get ready for a day of crisp fall air, weird history, and classic Catskills vibes. After the hike, we’ll warm up with food and drinks before heading back to the city.

REGISTER HERE TO ATTEND https://joinoutsiders.com/events

EVENT TIMELINE:
📍 10:00 AM – Meet at The Standard Biergarten (Meatpacking)
🚌 10:30 AM – Depart NYC
🥾 12:45 PM – Arrive at trailhead and begin hike
👻 2:30 PM – Explore hotel ruins + summit views
🎉 3:30 PM – Head to post-hike food and drinks
🚌 6:00 PM – Depart back to NYC
Event times are approximate and subject to group pace and traffic.

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WHAT’S INCLUDED IN YOUR TICKET:
✅ Roundtrip transportation from NYC
✅ Guided hike to Overlook Mountain ruins
✅ Complimentary water from Spindrift
✅ Post-hike beverages by Lone River

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HIKE DETAILS:
🎃 Difficulty: Moderate
📏 Distance: ~5 miles out-and-back
📈 Elevation Gain: ~1,400 ft
🔗 View the trail on AllTrails

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WHAT TO BRING:

• Sturdy hiking shoes or boots
• Weather-appropriate clothing (layers encouraged)
• Plenty of water (1–2L recommended)
• Snacks or light lunch
• Costume (optional, but encouraged!)
• A sense of adventure... and maybe a flashlight 🕯️

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Expect ruins. Expect views. Expect some haunted Catskills history.
Spots are limited — grab yours now and join us for a Halloween hike to remember. 🧟🍁👻

REGISTER HERE TO ATTEND https://joinoutsiders.com/events

Join us for a hike that combines history and stunning views: the Van Slyke Castle Ruins Hike. You’ll start on tranquil forest trails that gradually lead to the eerie yet captivating Van Slyke Castle ruins. Once a grand estate, the crumbling walls now stand as a haunting reminder of the past, making it a perfect spot for exploration and photography. After soaking in the castle's history, continue to the ridge for panoramic views of Ramapo Lake and the surrounding mountains, giving you plenty of awe-inspiring moments. This hike has a bit of everything—from peaceful wooded paths to rugged sections—ideal for those seeking an adventurous trek with a historical twist.
Bring your hiking shoes or sturdy sneakers (you’ll need them), pack water and a sandwich, invite some friends (or come solo), and get ready to enjoy the outdoors. We’ll start the day at The Standard Biergarten in Chelsea. After the hike, we'll make a stop for food and drinks before heading back to NYC.
EVENT DETAILS:

• 10:00 AM – Meet at The Standard Biergarten
• 3:00 PM – Conclude hike head to food and drinks
• 7:30 PM - Back to NYC

(All times are approximate and subject to change based on traffic and group pace)
What's included in your ticket:

• Transportation
• Guided Hike
• Water Provided by Spindrift
• Beer provided by Voodoo Ranger

HIKE DETAIL:

• Moderate
• MILEAGE: 5.5 miles
• ELEVATION: 774ft
• View the trail details here https://www.alltrails.com/ar/trail/us/new-jersey/ramapo-mountain-yellow-and-cannonball-trail