OUTSIDERS Chicago

Lake Front Group Walk

02 may 2026 7:30 CDT

South Shore Cultural Center, 7059 South South Shore Drive, Chicago, IL, US

MAKE SURE TO REGISTER HERE TO ATTEND

Some days, you just need to move. Together.
We're walking the full length of Chicago's lakefront, start to finish, as a crew. South Shore Cultural Center to Osterman Beach, sixteen miles up the lake with your people. The skyline, the beaches, the neighborhoods changing around you, and good company the whole way.
No pressure on pace, no pressure on distance. Jump in at the start or catch us at Navy Pier or North Avenue Beach. Stay for a stretch or go the whole way. The only rule is you show up.
Chicago is best on foot. Let's remind ourselves why.
Doors open at 7:30 AM at South Shore Cultural Center. See you out there.
Route & Schedule
Start 7:30 AM - South Shore Cultural Center
South Side 8:10 AM - 63rd Street Beach (~2 miles) Quick join point, warm-up stretch
9:00 AM - Promontory Point (~4 miles) Regroup stop, 10-15 min. Bathrooms + great views.
Downtown 10:15 AM - Museum Campus (~6.5 miles) Easy CTA access, good join point
10:45 AM - Grant Park (~8 miles)
11:15 AM - Navy Pier (~9-10 miles) Main regroup stop, 20-30 min. Best place to join mid-walk. Snacks, bathrooms, and water here.
12:00 PM - Ohio Street Beach (~10 miles)
North Side 12:45 PM - North Avenue Beach (~12 miles) Optional regroup stop, 10-15 min.
1:45 PM - Belmont Harbor (~14 miles)
2:30 PM - Montrose Beach (~16 miles) Last chance to join.
Finish 3:15-3:30 PM - Osterman Beach
The details Total distance: ~17 miles Total time: ~8 hours with breaks Pace: ~3 mph
Joining mid-walk? Pick any stop on the route. We'll be running roughly on schedule, give or take 15 minutes depending on pace. A group chat will be active on the day with live updates and a location pin so you can find us.

OREGON COAST ADVENTURE

21 may 2026 12:00 CDT

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

Nature Kayak Day

30 may 2026 10:00 CDT

Brooklyn Boulders, 100 South Morgan Street, Chicago, IL, US

MAKE SURE TO REGISTER HERE TO ATTEND.
https://joinoutsiders.com/chicago

Spend a day on the water paddling a gently winding stretch of river surrounded by turtles, birds, and lush riverbank vegetation. With natural rest spots along the way and transportation handled, all you have to do is show up and enjoy the ride.
Transportation departs from First Ascent (formerly Brooklyn Boulders) Chicago, West Loop 10:30 AM - Depart by 15 passenger van (West Loop). Wear water shoes or sandals, and pack a water bottle and a sandwich for the day.
Schedule
10:00 AM - Meet at First Ascent
12:30 PM - Arrive at kayak launch (7049 Pioneer Rd, Richmond, IL)
3:45 PM - Conclude on the water, depart for home
Timing is approximate and will vary with traffic and group pace.
What's Included
Kayak rental, round-trip transportation, guided tour, OUTSIDERS team leaders, and post-paddle beverages.

Turkey Summer Adventure

25 jun 2026 12:00 CDT

ontur hotel konak, İsmet Kaptan, Gazi Blv. No:130, 35241, izmir, TR

FOR MORE DETAILS AND TO REGISTER PLEASE CLICK HERE

### Welcome to Türkiye

We’re so excited to be spending part of the summer in Türkiye. With its sun-drenched coastlines, lively seaside towns, and rich blend of ancient and modern culture, Türkiye is the perfect place to soak up the season. This will be an unforgettable break filled with warm nights, turquoise waters, and vibrant city energy. Plan to meet new friends while exploring bustling bazaars, dancing to music that spills into the streets, and indulging in everything from meze feasts to perfectly grilled kebabs along the Aegean coast.

## Arrive in Izmir and Enjoy a Mediterranean Dinner

### Izmir Arrival

Arrive in Izmir, a seaside city with pastel sunsets and cafes that spill onto the sidewalks.

### Welcome Mediterranean Dinner

We’ll start our trip at a local restaurant with a relaxed Mediterranean dinner, enjoying sweeping panoramic views of the city.

DAY 2

### Alacati Boat Tour and Swimming

We’ll start with a sun-lit drive to a local seaside town and head to the local marina for a daylong boat tour. We’ll leisurely visit local coves and pause to float, swim or just enjoy the view of the coastline and turquoise waters. By sunset, the captain will turn back to Alacati leaving you with sun-kissed skin and salty hair.

### Evening Stroll and Dinner in Alacati

In the evening, we’ll return to Alacati to stroll along a glowing maze of cobblestone streets, restaurants, wine bars, and tiny boutique shops that stay open late. Among the music, mosaic lights and humming crowds, we’ll grab dinner, ice cream, cocktails and whatever else your heart desires.

DAY 3

### Windsurfing Lesson and Beach Day

We’ll continue our adventure in Alacati by heading to a local beach to learn how to windsurf from experienced instructors. You’ll practice the basics on the sand before venturing into the water to find your rhythm with the wind. By midday, you’ll take a break at a beach club and then spend the afternoon practicing or enjoying the water.

### Evening in Alacati

After a long day of enjoying the beach, we’ll head back to Alacati for a cozy dinner among the string lights and get our last taste of Alacati nightlife.

DAY 4

### Explore Ephesus Archaeological Ruins

You’ll wander slowly through archaeological ruins, learning about Greek & Roman history and architecture from a local guide. The morning will be full of quiet reflection among ancient walls and the serene grandeur of the preserved past.

### Visit House of the Virgin Mary

From there, we’ll head along a winding road to visit the House of the Virgin Mary, where many believe Mary spent her final years.

### Horseback Riding Tour

After a leisurely lunch, we’ll head to a nearby ranch and be matched with horses for a gentle tour along the countryside. As the sun lowers, we’ll head back to the ranch with a content feeling of a full day.

### Stay in Kusadasi

Stay locally in Kusadasi after a day of exploring ancient sites and horseback riding.

DAY 5

### Boat Cruise to Dalyan Delta

We’ll board a boat for another daylong trip heading towards the Dalyan Delta, then past ancient Lycian rock tombs.

### Mud Bath Experience

We’ll pause to dip into warm, mineral-rich mud baths that leave your skin glowing after you rinse off in the cool river.

### Visit Turtle Beach

We’ll stop by a local beach known as a sanctuary for sea turtles, before heading back to enjoy dinner and nightlife in Bodrum.

DAY 6

### Early Morning Walk to Bodrum Windmills

We’ll begin this day before the world wakes, with an (optional) early morning walk to the old stone windmills in Bodrum. We’ll watch the sun rise and change the colors of the coastline.

### Snorkeling Tour in Bodrum

After sunrise, we’ll head to the marina and jump onboard for a snorkeling tour. In between swimming with the local fish, you’ll enjoy the sun on the boat deck.

### Local Beach Day (Alternative Option)

For those who aren’t interested in snorkeling, the alternative option is a sun-filled local beach day.

DAY 7

After your days on the Aegean, we’ll take a short flight to Istanbul to enter a different world - of minarets, palaces, and the deep hum of a city that has stood for centuries.

### Historical Hamam Spa and Exfoliation

We’ll all go to a historical hamam for an afternoon spa & exfoliation treatment. After relaxing in the warm waters and drinking Turkish tea, we’ll make our way to the Bosphorus for a sunset cruise.

### Bosphorus Sunset Cruise

You’ll drift between Europe and Asia as you watch the sun set, and the lights softly illuminate the silhouette of the city.

DAY 8

### Guided Adventures in Istanbul

On your last day in Turkiye, we’ll offer multiple guided adventures, or you can enjoy the city of Istanbul at your own pace.

### Rooftop Dinner in Istanbul

We’ll end the trip with a rooftop dinner and panoramic views of Istanbul’s glittering landscape.

DAY 9

### Flights home

Whether you leave with a suitcase of souvenirs or just stories, you’ll carry Türkiye with you.

FOR MORE DETAILS AND TO REGISTER PLEASE CLICK HERE