Upcoming Chicago Adventures
Once you click "Register" please scroll up for purchase info and instructions.
Sunset City Paddle Adventure
Fri, Jul 18, 7:30pm - 9:30pm CDT
Channel your inner summer vacation self—without ever leaving the city. Join us for a playful, soul-refreshing sunset paddle on Lake Michigan, where you'll have the option to stand up paddleboard or kayak as the sun dips below the horizon at 8:27 PM.
We’ll launch from North Avenue Beach and paddle into golden hour, with the city skyline glowing behind us and warm summer air all around. Whether you're looking to reconnect with nature, try something new, or just unwind with a little splash and sunshine, this 2-hour lake adventure is your chance to embrace summer the way it was meant to be.
No experience? No worries—we’ve got you covered with equipment, instruction, and all the good vibes.
-
Your choice of SUP or kayak rental
Light instruction + group paddle guidance
A 2-hour summer sunset experience on the water
First-timer or seasoned paddler—this is your chance to feel like a kid on summer break again. Come solo or bring a friend. Either way, you won’t want to miss this magical evening on the lake.
River Tubing CHI 2025
Sun, Aug 3, 9am - 6pm CDT
Join us for River Tubing on Saturday, August 3rd!
Enjoy a scenic, lazy, and fun-filled float down the beautiful Tippecanoe River in Winamac, Indiana. This 3-hour tubing journey is the perfect way to soak in summer vibes with great company, cold drinks, and outdoor adventure.
We’ll kick off the day at Brooklyn Boulders Chicago at 9:00 AM, where you’ll check in and meet your fellow tubers. We’ll have beers and other beverages ready for you—and feel free to bring your own favorites along too!
-
Round-trip Transportation
River Tubing Ticket
Beer & Other Beverages
-
09:00 AM (CST) – Meet at Brooklyn Boulders Chicago
09:30 AM (CST) – Depart for tubing site
01:00 PM (CST) – Arrive at Tippecanoe River
5:15 PM (CST) – Depart back to Chicago
Follow us on Instagram @outsiders.chi