Outsiders NY

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

Join us for an unforgettable day of scenic trails and savory bites!
We're heading out for a beautiful hike along the Diamond Mountain Trail in Harriman State Park, known for its quiet forest paths, rolling ridgelines, and panoramic views. This moderate loop is the perfect mix of peaceful woods and rewarding outlooks, especially with the first waves of fall color creeping into the trees.
After the hike, we'll treat ourselves to a well-deserved meal and drinks at a local eatery. Whether you're after a hot meal, a cold drink, or simply a stunning view to toast the day, it's the perfect way to cap off an afternoon on the trail.
EVENT DETAILS

• 10:00 AM: Meet at The Standard Biergarten (Meatpacking)
• 10:30 AM: Depart NYC
• 12:00 PM: Arrive at trailhead and begin hike
• 1:30 PM: Snack break on the trail
• 3:00 PM: Conclude hike and head to local eatery
• 5:30 PM: Depart back to NYC

All times are approximate and subject to change based on group pace and conditions.
WHAT'S INCLUDED IN YOUR TICKET

• Roundtrip transportation from NYC
• Guided hike on the Diamond Mountain Trail
• Beverages on the way home

HIKE DETAILS

• Trail: Diamond Mountain Trail
• Location: Harriman State Park
• Mileage: 5 miles
• Elevation Gain: 866 ft
• Difficulty: Moderate (some elevation and rocky terrain)
• View trail on AllTrails

WHAT TO BRING

• Comfortable hiking shoes or trail sneakers
• Weather-appropriate clothing
• Packed water and trail snacks
• A hearty appetite and a spirit for adventure

IMPORTANT SAFETY NOTES

• Unsuitable footwear or clothing may result in removal from the hike for safety reasons.
• Please consult your doctor if you have medical conditions that may affect your ability to participate.
• A signed waiver is required to join the trip.

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

Ready for a hike with a little adventure built in? Join us for one of the most fun and unique trails in the Hudson Valley, the legendary Lemon Squeeze at Mohonk. This is part hike, part rock scramble, as we climb through the Labyrinth, a natural maze of towering boulders, tight crevices, and wooden ladders, before squeezing through the famous Lemon Squeeze and emerging at Sky Top for jaw-dropping panoramic views of the Shawangunk Ridge and the valley below, all lit up in peak fall color.
It's a hands-on, full-body adventure that rewards every scramble with unforgettable scenery. After we come back down to earth, we'll head into charming New Paltz to refuel with food and drinks before heading back to the city.
PLEASE NOTE: This is an advanced hike. If you have any doubts of your ability please reach out to us at info@joinoutsoders.com
EVENT TIMELINE

• 10:00 AM: Meet at The Standard Biergarten (Meatpacking)
• 10:30 AM: Depart NYC
• 12:30 PM: Arrive at Mohonk Preserve and begin hike
• 2:00 PM: Scramble through the Labyrinth and the Lemon Squeeze
• 2:30 PM: Summit Sky Top for photos and panoramic views
• 3:30 PM: Descend and complete the hike
• 4:30 PM: Head to a local eatery in New Paltz for food and drinks
• 6:00 PM: Depart back to NYC
• 8:00 PM (approx.): Arrive back in the city

All timing is approximate and subject to change based on group pace and conditions.

## WHAT'S INCLUDED IN YOUR TICKET

• Roundtrip transportation from NYC
• Guided hike led by OUTSIDERS hiking guides
• Parking and trail access fees
• Complimentary water and beverages on the ride home

## HIKE DETAILS

• Trail: The Labyrinth and Lemon Squeeze to Sky Top
• Location: Mohonk Preserve, Shawangunk Mountains
• Mileage: approx. 3 miles
• Difficulty: Moderate with a strenuous rock scramble
• Terrain: boulder scrambles, narrow rock passages, and wooden ladders

(Trail details to be finalized)

## WHAT TO BRING

• Sturdy sneakers or hiking shoes with good grip (a must!)
• Layers and weather-appropriate clothing
• Water bottle
• Snacks or trail lunch
• A small, close-fitting backpack (large packs make the squeeze tricky)
• A sense of adventure!

## IMPORTANT NOTES

• The Lemon Squeeze involves climbing ladders and squeezing through very narrow rock passages. It is not recommended for anyone with claustrophobia or significant mobility limitations.
• Our adventures are full-day experiences. We do not recommend scheduling other activities that day, as return times can vary.
• Unsafe or unsuitable attire and footwear may result in denied participation for safety reasons. Proper footwear with good traction is required.
• If you have any medical conditions or injuries that might prevent you from safely completing the scramble, please consult your physician before signing up.
• A signed waiver is required to join the trip.

Come climb, squeeze, and scramble your way to one of the best views in the Hudson Valley at the height of fall.

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

Hop aboard for one of the most unique and scenic adventures of the season, a Rail Explorers ride through the heart of the Catskills. Cruise along historic railroad tracks in a custom pedal-powered rail car, soaking in the crisp mountain air and breathtaking early fall views at every turn.
This 2.5-hour guided tour follows the historic Ulster & Delaware Railroad corridor, gliding through golden forests, over old trestle bridges, and alongside the tranquil Esopus Creek. It's part leisurely ride, part light cardio, and all-around fun, no experience required.
EVENT TIMELINE:

• 12:30 PM: Meet at The Standard Biergarten (Meatpacking)
• 1:00 PM: Depart NYC
• 3:30 PM: Rail Explorers tour begins
• 5:30 PM: Tour ends, hangout time
• 6:00 PM: Head to a local eatery for food and drinks
• 8:00 PM: Head back to NYC
• 10:30 PM (approx.): Arrive back in the city

All timing is approximate and subject to group pace and traffic.
TICKET INCLUDES:

• Roundtrip transportation from NYC
• Rail Explorers ticket + railbike rental
• Drinks for the ride
• A full day of upstate adventure with new friends

WHAT TO BRING:

• Comfortable clothes for light activity
• Sneakers or closed-toe shoes (required!)
• Sunglasses and sunscreen
• Light jacket (fall air can be crisp!)
• Reusable water bottle
• Snacks or lunch

IMPORTANT NOTES:

• Proper attire is required for safety. If your clothing or footwear is deemed unsuitable, we reserve the right to turn you away.
• Please consult your doctor if you have any conditions that may impact your ability to participate.
• A signed waiver is required to join the trip.
• Our adventures are full-day experiences. We do not recommend scheduling other activities that day, as return times can vary.

Don't miss this chance to escape the city and ride the rails in style. Spots are limited, so grab yours now and let's cruise the Catskills.

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

Hit the trail with a pup and your people!
Social Paws and OUTSIDERS are teaming up for a dog-friendly group hike just outside the city, designed for anyone who loves dogs, getting outdoors and/ or wants to bring their four-legged friend along for the adventure.
We'll head out of NYC together via private transportation, hike a scenic trail at a relaxed pace, and soak up plenty of time for bonding, fresh air, and connection amid peak fall color. Afterward, we'll roll into Twin Star Orchards for some eats, a dog-centric local market curated just for the Social Paws crew, a short tour with orchard staff, and a few refreshing ciders before we bring everyone back to the city.
WHAT'S INCLUDED IN YOUR TICKET

• Round-trip transportation from NYC
• Guided hike led by OUTSIDERS hiking guides
• Parking and trail access fees
• Breakfast on board (Levain cookies and NYC bagels)

SCHEDULE FOR THE DAY

• 9:00 AM: Meetup
• 9:30 AM: Departure
• 11:45 AM: Arrival at the park, begin hiking
• 3:00 PM: Complete hike
• 3:30 PM: Arrive at Twin Star Orchards for the local pup market, food, and tour
• 5:30 PM: Departure
• 7:00 PM: Return to NYC

WHAT TO BRING

• Sturdy hiking boots
• Layers (fall weather can be unpredictable)
• Water and trail snacks
• Leash, doggie bags, water bowl, wipes for dirty paws, and anything else your dog needs on trail
• An appetite for adventure and a love of dogs!

TRAIL INFO This is a 5.1-mile hike with 672 ft of elevation gain, circling a lake before gradually ascending to a clifftop overlook. The trail is dog-friendly, with some narrow sections, a stream crossing, and a few steep areas.
FAQ
What isn't included in the ticket? Meals are on your own and available for purchase at Twin Star Orchards: https://www.twinstarorchards.com/menu
How much time should I allot for this? Our adventures are full-day trips. We don't recommend scheduling other activities on days you attend, especially since return times can be unpredictable.
Is the hike guided? This hike is 100% guided by OUTSIDERS hiking guides. One leads and one stays at the back of the group to account for different pace levels. The intention is to foster connection in a group setting. This hike is beginner-friendly and meant to be fun, not fast.
What weather conditions would lead to a cancellation? Extreme weather (storms, high winds) will lead to a cancellation. If driving is unsafe due to major storms, we will cancel. But we're looking forward to crisp, beautiful fall weather at the end of October!
I'd love to bring my dog. What do I need to know? Dogs must be comfortable around other dogs and people. We'll provide breaks for water, sniffing, and photos along the way.
I don't have a dog. Can I still come? Of course! Whether you're solo or with a furry friend, you and your pup are both welcome.