Outsiders NY

Oregon Coast Adventure

Thu, May 21 · 10:00 AM EDT

Portland, Oregon, 000, Portland, OR, US

For more details and tickets to this trip please visit
https://outsiders.wetravel.com/i/6939acb1e7096554c1efa406#day-1-portland-arrival-and-astoria-exploration

Oregon’s wild beauty is calling! This 5-day adventure takes you from Portland to the rugged Oregon Coast and deep into the lush forests of the Pacific Northwest. We’ll chase waterfalls in the Columbia River Gorge, surf the waves at Cannon Beach, and explore the charming coastal towns of Manzanita and Tillamook. From hiking scenic trails and spotting sea lions to cozy evenings by the coast and local brews at Pelican or Public House Brewery, this trip blends outdoor adventure with Oregon’s laid-back charm. With nights spent between Portland, Cannon Beach, and the coast, you’ll experience the best of what makes Oregon so unforgettable.
After landing in Portland, Oregon on March 26, we’ll hop into the Outsiders vans and begin our journey toward the Oregon Coast, where our adventure kicks off. We’ll settle into our accommodations in Cannon Beach for the next two nights before diving into the week’s activities. Please plan to arrive in Portland before noon on May 21 to ensure a smooth start to the trip.

## Day 1 - May 21

Welcome to Oregon! After arriving in Portland, we’ll meet up at a designated meet up location and hit the road, heading northwest for a scenic two-hour drive to the charming coastal town of Astoria—where the Columbia River meets the Pacific Ocean.
Once we arrive, we’ll spend the afternoon exploring Astoria’s rich maritime history and quirky local attractions. We’ll stop by the Columbia River Maritime Museum to learn about the region’s seafaring past, visit the Oregon Film Museum—set inside the old jail featured in The Goonies—and, of course, swing by the iconic Goonies House for a photo op.
As evening sets in, we’ll stroll along the Astoria Riverwalk, watching ships glide by on the Columbia, or climb the Astoria Column for panoramic views of the town, river, and ocean beyond. We’ll wrap up the day with dinner and craft beer at Fort George Brewery or Buoy Beer Company, both local favorites serving up fresh coastal fare and laid-back vibes.
We’ll spend the night in Cannon Beach, resting up before continuing our Oregon coast adventure tomorrow.

## Day 2 - May 22

After breakfast, we’ll take a scenic 40-minute drive south to Ecola State Park, a coastal gem known for its mossy forests, dramatic cliffs, and sweeping ocean views. We’ll hike the Indian Beach Trail, which winds from Ecola Point to Indian Beach, offering lush forest paths, panoramic seaside vistas, and plenty of photo-worthy stops along the way.
In the afternoon, we’ll arrive in Cannon Beach, one of Oregon’s most picturesque coastal towns. Enjoy some free time exploring the charming downtown area—browse boutique shops, art galleries, and cozy cafés.
As the day winds down, we’ll gather on the shore to watch a stunning sunset at Haystack Rock, the iconic monolith rising from the surf. Dinner follows at Ecola Seafoods or Public Coast Brewing Co., where you can enjoy casual, local coastal fare.
Overnight in Cannon Beach.

## Day 3 - May 23

We’ll start the morning at Cleanline Surf Shop in Cannon Beach to pick up boards and wetsuits for a fun day on the water. Depending on surf conditions, we’ll ride the waves at Short Sand Beach in Oswald West State Park or Indian Beach—both surrounded by dramatic cliffs and lush coastal forest. Whether you’re new to surfing or an experienced wave rider, it’s a perfect way to immerse yourself in Oregon’s rugged coastline.
In the afternoon, you’ll have options to continue exploring or relax. Visit the nearby Hug Point caves and waterfall, a hidden coastal treasure, or spend some downtime back in town strolling the beach, grabbing a coffee, or browsing local shops.
We’ll wrap up the day with dinner and craft beer at Pelican Brewing, the ideal post-surf hangout to celebrate another incredible day along the Oregon Coast.
Overnight in Cannon Beach.

## Day 4 - May 24

We’ll start the morning with coffee and fresh pastries at Sleepy Monk Coffee Roasters, soaking in the last bit of Cannon Beach charm before we head inland. If you’d like one more coastal viewpoint, we’ll make an optional stop at the Neahkahnie Mountain overlook, where sweeping ocean vistas stretch for miles—an unforgettable final look at Oregon’s rugged shoreline.
From there, we’ll make the scenic 1.5–2 hour drive back toward Portland for lunch. We’ll then continue east for a short ride into the Columbia River Gorge, one of Oregon’s most iconic landscapes. We’ll spend the afternoon exploring some of the Gorge’s classic trails—your choice of the misty Latourell Falls, the iconic cascade at Multnomah Falls, or the panoramic climb to Angel’s Rest. Each option offers its own unforgettable perspective on the gorge’s cliffs, forests, and waterfalls.
After the hike, we’ll stop at the historic Vista House, perched high above the river, for sweeping views of the Gorge—an ideal spot for photos and a breather before the evening’s adventure.
At 6:00 PM, we’ll meet for a sunset kayaking session, paddling calm waters as the sky glows orange and pink behind basalt cliffs. It’s a peaceful, breathtaking way to experience the Gorge’s beauty at golden hour.
After kayaking, we’ll head back to Portland for the night, ready for a restful evening before the next day’s departure.

## Day 5 - May 25

We’ll make our way to the airport for departure, wrapping up an unforgettable five-day Oregon adventure.

OREGON COAST ADVENTURE

Thu, May 21 · 12:00 PM EDT

The Clyde Hotel, 1022 SW Harvey Milk St, Portland, OR 97205, Portland, OR, US

FOR MORE INFORMATION AND TO REGISTER PLEASE CLICK HERE

### Oregon Coast & Gorge Adventure

Oregon’s wild beauty is calling! This 5-day adventure takes you from Portland to the rugged Oregon Coast and deep into the lush forests of the Pacific Northwest. We’ll chase waterfalls in the Columbia River Gorge, surf the waves at Cannon Beach, and explore the charming coastal towns of Manzanita and Tillamook. From hiking scenic trails and spotting sea lions to cozy evenings by the coast and local brews at Pelican or Public House Brewery, this trip blends outdoor adventure with Oregon’s laid-back charm. With nights spent between Portland, Cannon Beach, and the coast, you’ll experience the best of what makes Oregon so unforgettable.

DAY 1

### Arrival in Portland

Welcome to Oregon! After arriving in Portland, we’ll meet up at a designated meet up location and hit the road, heading northwest for a scenic two-hour drive to the charming coastal town of Astoria—where the Columbia River meets the Pacific Ocean.

### Explore Astoria’s Maritime History

Spend the afternoon exploring Astoria’s rich maritime history and quirky local attractions. Stop by the Columbia River Maritime Museum to learn about the region’s seafaring past, visit the Oregon Film Museum—set inside the old jail featured in The Goonies—and swing by the iconic Goonies House for a photo op.

### Astoria Riverwalk and Astoria Column

Stroll along the Astoria Riverwalk, watching ships glide by on the Columbia, or climb the Astoria Column for panoramic views of the town, river, and ocean beyond.

### Dinner at Fort George Brewery or Buoy Beer Company

Wrap up the day with dinner and craft beer at Fort George Brewery or Buoy Beer Company, both local favorites serving up fresh coastal fare and laid-back vibes.

### Overnight in Astoria

We’ll spend the night in Astoria, resting up before continuing our Oregon coast adventure tomorrow.

DAY 2

### Scenic Drive to Ecola State Park

After breakfast, we’ll take a scenic 40-minute drive south to Ecola State Park, a coastal gem known for its mossy forests, dramatic cliffs, and sweeping ocean views.

### Hike Indian Beach Trail

We’ll hike the Indian Beach Trail, which winds from Ecola Point to Indian Beach, offering lush forest paths, panoramic seaside vistas, and plenty of photo-worthy stops along the way.

### Explore Cannon Beach Downtown

In the afternoon, we’ll arrive in Cannon Beach, one of Oregon’s most picturesque coastal towns. Enjoy some free time exploring the charming downtown area—browse boutique shops, art galleries, and cozy cafés.

### Sunset at Haystack Rock

As the day winds down, we’ll gather on the shore to watch a stunning sunset at Haystack Rock, the iconic monolith rising from the surf.

### Dinner at Ecola Seafoods or Public Coast Brewing Co.

Dinner follows at Ecola Seafoods or Public Coast Brewing Co., where you can enjoy casual, local coastal fare.

### Overnight in Cannon Beach

Overnight in Cannon Beach.

DAY 3

### Pick Up Surf Gear at Cleanline Surf Shop

We’ll start the morning at Cleanline Surf Shop in Cannon Beach to pick up boards and wetsuits for a fun day on the water.

### Surfing at Short Sand Beach or Indian Beach

Depending on surf conditions, we’ll ride the waves at Short Sand Beach in Oswald West State Park or Indian Beach—both surrounded by dramatic cliffs and lush coastal forest. Whether you’re new to surfing or an experienced wave rider, it’s a perfect way to immerse yourself in Oregon’s rugged coastline.

### Explore Hug Point Caves and Waterfall

Visit the nearby Hug Point caves and waterfall, a hidden coastal treasure, or spend some downtime back in town strolling the beach, grabbing a coffee, or browsing local shops.

### Dinner at Pelican Brewing

We’ll wrap up the day with dinner and craft beer at Pelican Brewing, the ideal post-surf hangout to celebrate another incredible day along the Oregon Coast.

### Overnight in Cannon Beach

Overnight in Cannon Beach.

DAY 4

### Coffee and Pastries at Sleepy Monk Coffee Roasters

We’ll start the morning with coffee and fresh pastries at Sleepy Monk Coffee Roasters, soaking in the last bit of Cannon Beach charm before we head inland.

### Optional Stop at Neahkahnie Mountain Overlook

If you’d like one more coastal viewpoint, we’ll make an optional stop at the Neahkahnie Mountain overlook, where sweeping ocean vistas stretch for miles—an unforgettable final look at Oregon’s rugged shoreline.

### Explore Columbia River Gorge Trails

We’ll then continue east for a short ride into the Columbia River Gorge, one of Oregon’s most iconic landscapes. We’ll spend the afternoon exploring some of the Gorge’s classic trails—your choice of the misty Latourell Falls, the iconic cascade at Multnomah Falls, or the panoramic climb to Angel’s Rest. Each option offers its own unforgettable perspective on the gorge’s cliffs, forests, and waterfalls.

### Visit Vista House

After the hike, we’ll stop at the historic Vista House, perched high above the river, for sweeping views of the Gorge—an ideal spot for photos and a breather before the evening’s adventure.

### Sunset Kayaking Session

At 6:00 PM, we’ll meet for a sunset kayaking session, paddling calm waters as the sky glows orange and pink behind basalt cliffs. It’s a peaceful, breathtaking way to experience the Gorge’s beauty at golden hour.

After kayaking, we’ll head back to Portland for the night, ready for a restful evening before the next day’s departure.

DAY 5

### Airport Departure

We’ll make our way to the airport for departure, wrapping up an unforgettable five-day Oregon adventure.

FOR MORE INFORMATION AND TO REGISTER PLEASE CLICK HERE

Pinelands Kayaking & BBQ

Sat, May 23 · 10:00 AM EDT

The Standard Biergarten, 848 Washington St, New York, NY, US

REGISTER HERE TO ATTEND https://joinoutsiders.com/events
Join us for an unforgettable kayaking adventure through the serene and scenic New Jersey Pinelands. This 2-hour paddle winds along a gently curving river that opens into a peaceful beaver pond, where you may spot beaver lodges, turtles, birds, and even fascinating carnivorous plants along the banks.
The pace is relaxed and beginner-friendly, with natural pull-off points where we can pause, float, and take it all in. It’s the kind of day that feels miles away from city life: quiet water, sun overhead, and nothing to do but paddle forward.
Bring your water shoes or sandals, pack water and a sandwich for before or after the paddle, and invite a friend. After we wrap on the river, we’ll head to a beloved local BBQ spot for a well-earned feast before making our way back to NYC. Smoky ribs, cold drinks, and post-paddle stories included.

### Event Details:

10:00 AM – Meet at The Standard Biergarten 10:30 AM – Depart NYC 12:30 PM – Arrive in the Pinelands + Begin Kayaking 3:15 PM – Conclude paddle + Head to Local BBQ Spot 5:00 PM – Depart back to NYC 7:00 PM – Arrive back in NYC
Times are approximate and subject to traffic and group pace.

### What’s Included in Your Ticket:

• Round-trip transportation
• Kayak rental + safety gear
• Guided paddle experience
• Water on the ride home
• Refreshments for the ride home
• OUTSIDERS host on site

### What to Bring:

• Water shoes or secure sandals (required)
• Comfortable, weather-appropriate clothing
• Water bottle
• Sunscreen + hat
• Towel + change of clothes
• Waterproof bag (Also available for purchase)
• Card/cash for BBQ

### Important Notes:

• 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.
• If you are not dressed in weather-appropriate gear or 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.

The Fire Tower Quest: Hiking the Catskills Series

Sun, May 24 · 7:00 AM EDT

The Standard Biergarten, 848 Washington St, New York, NY, US

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

Welcome to The Fire Tower Quest: an ongoing OUTSIDERS hiking series dedicated to summiting the iconic fire towers of the Catskills.
These historic towers rise above the forest canopy, rewarding those who climb them with panoramic views that stretch for miles. Each quest takes us up a different Catskills peak, with steady climbs, rocky sections, forested switchbacks, all leading to that final metal staircase and the unbeatable view at the top.
For those who visit all Catskills fire towers in 2026, you’ll earn your first hiking patch with the New York State Department of Environmental Conservation. Learn more here: https://dec.ny.gov/things-to-do/hiking/catskills-fire-tower-challenge
This series is about more than checking off summits. It’s about earning perspective. Moving with purpose. Building grit. And sharing the climb with people who show up ready to push themselves.
Come ready to hike. Leave with a new summit under your belt.

### EVENT DETAILS:

7:30 AM - Meet 8:00 AM - Depart 10:30 AM - Arrive at Trailhead + Begin Hike 4:30 PM - Complete Hike + Head to Dinner 6:30 PM - Drive back to NYC 9:00 PM - Return Home
All times are approximate and subject to traffic, weather, and group flow.

### Included in Your Ticket:

• Round-trip transportation
• Guided hike with OUTSIDERS professional guides
• Fire Tower summit experience
• Post-hike refreshments

### What to Bring:

• Proper hiking boots (required)
• Plenty of water: 1L per 4 miles
• Packed snacks
• Weather-appropriate layers

### Hike Details:

• Difficulty: Moderate to challenging
• Mileage: ~7 miles
• Elevation Gain: ~1800+ ft
• Terrain: Rocky sections, uneven footing

### Important Notes:

• Our adventures are full-day experiences. We do not recommend scheduling other activities that day, as return times can vary.
• Proper hiking boots are required. Unsafe attire may result in denied participation for safety reasons.If you are not dressed in weather-appropriate gear or 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.
• A signed waiver is required.