What we’re about
The Outsiders is a New York-based social club. Our mission is to bring people together, foster a sense of community, and develop meaningful connections through shared outdoor experiences. We work hard to keep these adventures affordable and accessible to provide more people with the opportunity to join us and experience the outdoors.
The Outsiders are made up of social butterflies, urban explorers, music lovers, outdoor enthusiasts, thrill seekers, creatives, foodies -- in essence we are New Yorkers looking for our next adventure with like-minded people.
Upcoming events (4+)
See all- The Caribbean Ride 2025Unlimited Biking, New York, NY
To attend YOU MUST PURCHASE TICKETS HERE: https://joinoutsiders.com/events
Join Us for The Caribbean Ride — Supporting Caribbean Small Businesses!
Get ready to pedal with purpose! We’re kicking off our ride at Columbus Circle, Manhattan, then cruising into Brooklyn for a vibrant tour through some of the most authentically Caribbean neighborhoods. Along the way, we’ll be stopping at a few standout local eateries to experience the flavors of the islands.
Date: Saturday, August 9th
Start Time: 12:00 PM
Distance: 22 miles (over ~4 hours, including stops)
Meeting Location:
Unlimited Biking
56 W 56th St, New York, NY 10019
🔗 CLICK HERE FOR THE FULL ROUTE MAP AND STOPS (Subject to change)
📝 FILL OUT THE WAIVER BEFORE ATTENDING
Need a bike? Rent one through our partners at Unlimited Biking — don’t forget to use the OUTSIDERS discount!***
What to Bring:
- Your own bike (BYOB!)
- Water (it’s going to be a hot one!)
- Sunscreen
- Good vibes and high energy
Important Notes:
- Reservations are required in advance.
- You’re welcome to leave the ride at any point — just make sure to start with us at Unlimited Biking.
Come ride with us, support Caribbean culture, and celebrate summer with a purpose. See you there!
To attend YOU MUST PURCHASE TICKETS HERE: https://joinoutsiders.com/events
- City Sunset Kayak AdventureManhattan Kayak Company, New York, NY
To attend YOU MUST PURCHASE TICKETS HERE: https://joinoutsiders.com/events
Join Us for Night Kayaking on the Hudson River
Sunday, August 10th
Get ready for an unforgettable evening adventure! Join us on Sunday, August 10th for a scenic night kayaking trip on the Hudson River. Take in stunning panoramic views of Manhattan’s iconic skyline as we paddle 45 minutes up the Hudson and 45 minutes back down.
Meeting Location:
Pier 84 Boathouse
555 12th Ave at West 44th St
New York, NY 10036
Please arrive on time—we follow a strict schedule. If you’re late, the guide will launch without you and no refunds will be issued.
To ensure safety, we’ll split participants into two groups.- Group 1 launches at 7:00 PM
- Group 2 launches at 8:00 PM
While you wait, enjoy games and social activities on the dock!
***
#### EVENT SCHEDULE
6:30 PM – Arrival & Introduction
6:45 PM – Suit Up
7:00 PM – Group 1 Launch
8:00 PM – Group 2 Launch
9:00 PM – Tour Ends***
IMPORTANT INFO
- No prior kayaking or swimming experience required
- Maximum weight limit: 225 lbs per person
***
#### WHAT TO BRING
- Clothes that can get wet (quick-dry, water-friendly materials like spandex, Dri-Fit, or swimsuits)
- Avoid cotton, jeans, and flip-flops
- Shoes that can get wet
- Change of clothes for after the tour
- A lock for the lockers
- Water bottle and a light snack
- Waterproof phone case (recommended)
***
#### WE PROVIDE
- Sit-on-top kayak, paddle, life jacket, and guide
- Restrooms, changing rooms, lockers, and an outdoor shower
***
Don’t miss this unique chance to paddle under the stars with NYC as your backdrop!
To attend YOU MUST PURCHASE TICKETS HERE: https://joinoutsiders.com/events
- Azores, PortugalNeeds location
To attend YOU MUST PURCHASE TICKETS HERE: https://joinoutsiders.com/azores
### AT A GLANCE
Prepare for an unforgettable adventure in the Azores' Sao Miguel and Pico Islands! Sao Miguel's lush landscapes and hot springs await, while Pico's volcanic peak offers thrilling hikes. Embrace island life as you indulge in local cuisine, mingle with friendly locals, and soak up the laid-back atmosphere. Explore breathtaking scenery, rich culture, and warm hospitality in the Azores this August.
*Itinerary subject to changeITINERARY*
### WHAT TO EXPECT
In August, Sao Miguel and Pico Islands in the Azores beckon with a vibrant tapestry of adventure and relaxation. Picture yourself lounging on sun-kissed beaches, the gentle lull of the Atlantic Ocean providing a soothing soundtrack. Wander through quaint villages on Sao Miguel, where cobblestone streets wind past pastel-colored houses adorned with blooming flowers. Embark on exhilarating hikes on Pico, surrounded by towering volcanic peaks and verdant vineyards. Amidst this breathtaking scenery, immerse yourself in the warmth of Azorean hospitality, savoring traditional cuisine and forging unforgettable memories in these island paradises.
*itinerary subject to change## Day 1 - August 16 ARRIVAL
SÃO MIGUEL
TRAVEL DAY
Enjoy the hotel / pool## Day 2 - August 17
SÃO MIGUEL
Lagoa das Sete Cidades - Miradouro da Boca do Inferno - Parque Terra Nostra
Get ready for an amazing day in the Azores that you won't forget. We'll start off surfing then well go to Lagoa das Sete Cidades, where the views are straight out of a postcard. Then, we'll head over to Miradouro da Boca do Inferno to soak in the stunning coastal scenery. After that, it's time to relax in the peaceful oasis of Parque Terra Nostra before we dive into the geothermal wonders of Furnas. And guess what? We'll wrap up the day with a delicious late lunch at Tony's, where we'll taste some mouthwatering Azorean dishes.## Day 3 - August 18
SÃO MIGUEL
Faial da Terra ⁃ Salto do Prego ⁃ Sanguinho ⁃ Miradouro da Ponta da Madrugada ⁃ Miradouro da Ponta do Sossego
We'll start our adventure in Furnas, immersing ourselves in its natural beauty. Our next stop will be canyoneering, where we'll experience thrilling adventures.And just when you thought it couldn't get any better, we'll wrap up the day at Miradouro da Ponta do Sossego, where you can take in the sunset over the Atlantic in all its glory.## Day 4 - August 19
SÃO MIGUEL / PICO
TRAVEL DAY
Fly from São Miguel to Pico## Day 5 - August 20
PICO
Get ready for an incredible first day on Pico Island! We'll start with thrilling whale watching, then cool off at natural swimming pools. Finally, we'll head to Ponta da Ilha for stunning coastal views.## Day 6 - August 21
PICO
We'll explore Gruta da Torre, then head to Criação Velha for some island charm. Next up, we'll relax at Lagido, enjoying the scenic beauty. Finally, we'll top it off with a wine tasting at sunset followed by dinner at Cela Bar.## Day 7 - August 22
PICO / SÃO MIGUEL
FLY BACK TO SÃO MIGUEL MORNING
Once we get back to Sao Miguel, we'll start with a delicious lunch at Caloura followed by some relaxation time at the beautiful beach. Then, we'll hop on a late afternoon boat ride (TBD) for some scenic views. To end the day perfectly, we'll enjoy our last dinner together.## Day 8 - August 23
DEPARTURE
After an unforgettable week in the Azores, we’ll say our goodbyes and make our way back home.HERE’S THE BREAKDOWN OF
### WHAT’S INCLUDED
- Hotel Accommodations in Sao Miguel
- Private Traditional Azorean Accommodations in Pico
- Round trip flight Sao Miguel to Pico
- Transportation throughout the week
- Breakfast at the Hotel
- 4 Dinners
- All Tours
- Hikes
- Surfing
- Waterfall Rappelling
- Canyoneering
- Site Seeing
Please Note: Airfare to Sao Miguel from your respective cities is not included in this package. Also not included is a tip for our local guide.
To attend YOU MUST PURCHASE TICKETS HERE: https://joinoutsiders.com/azores
- Catskills Swimming HoleThe Standard Biergarten, New York, NY
Join us for a refreshing day trip to one of the Catskills' most scenic swimming holes.
To attend YOU MUST PURCHASE TICKETS HERE: https://joinoutsiders.com/events
This all-day escape is your chance to hike, swim, sunbathe, and recharge in the heart of nature—just a few hours from NYC.
We’ll kick things off with a morning meetup at The Standard Biergarten in Chelsea before hopping on a private bus to the mountains. After a short, guided hike through lush forest trails, we’ll arrive at our secret swimming hole—an idyllic spot surrounded by nature where you can take a dip, relax on the rocks, or bask in the sunshine. Bring your crew or come solo—either way, you'll leave feeling refreshed and connected.
EVENT SCHEDULE
9:00 AM – Check-in at The Standard Biergarten, Chelsea
9:30 AM – Depart NYC
12:00 PM – Arrive at trailhead & hike to the swimming hole
1:00 PM – 4:30 PM – Swimming hole hangout: swim, relax, and soak in the scenery
4:30 PM – Begin return trip to NYC
(All times are approximate and subject to change based on traffic and group pace)What’s Included:
- Roundtrip transportation from NYC
- Guided hike to and from the swimming hole
- Ice-cold beer and other beverages
What to Bring:
- Swimsuit & towel
- Sturdy sneakers or hiking shoes (a must for trail terrain)
- Reusable water bottle
- A packed lunch or sandwich
- Sunscreen, hat, and anything else you need for a chill day outdoors
Come ready for a carefree, childlike summer adventure—right in the heart of the Catskills. Space is limited.
