Events & gallery

Where we're headed, and where we've been.

From weeknight paddles on Lake Michigan to championship channels in Hawaii, here's the season ahead and the wake behind us.

Upcoming

This season's paddles & races.

Our regular practices run out of the North Shore Yacht Club through the warm months, and crews travel to race across the Midwest and beyond.

+Weekly
Home · NSYC

Club practice & new-paddler nights

Open-water sessions out of Highland Park through the season. Newcomers welcome — message us to claim a seat.

JulSummer
Regional

Outrigger Canoe Sprint Regatta

Short, fast flat-water sprints — a great first race for newer paddlers and a speed test for the crew.

JulSummer
Home · NSYC

Beach 2 Beach

Our home-water race right off the North Shore Yacht Club in Highland Park — open-water distance paddling for OC, surfski, and SUP. Registration through PaddleGuru.

AugSummer
Away · New York, NY

Hudson River Cup

An OC-6 race on the Hudson hosted by Kealoha Outrigger — our East Coast target race for late summer.

SepFall
Away · Catalina Island, CA

Catalina Crossing — US Outrigger Championships

The 26-mile channel crossing that started it all for us back in 2012. Still the bucket-list race for the club.

OctFall
Away · Molokaʻi → Oʻahu, HI

Molokaʻi Hoʻe

The OC-6 world championship across the Kaʻiwi Channel — the pinnacle of the sport, and a course OC members have crossed.

OctFall
Away · Chattanooga, TN

Chattajack

A 31-mile downriver paddle on the Tennessee River — a bucket-list endurance race to close the season.

NovFall
Away · Miami, FL

Nish Outrigger Challenge

A challenging and fun race near the end of our season.

+Midwest
Regional · IL & beyond

Midwest river & lake races

River marathons and regional regattas like the Des Plaines River Marathon and Fox River Classic round out the calendar.

Dates and race lineup vary year to year. For confirmed dates and travel plans, follow us on Instagram / Facebook or email outriggerchicago@gmail.com.

Past events

Photo gallery.

A few frames from the beach and the boat. Got a great shot from a race or practice? We'd love to add it.

Check out our Instagram and Facebook pages for more pics.

In the wake

A few highlights from the crew.

Outrigger Chicago paddlers have shown up at start lines from the Midwest to the middle of the Pacific.

2012Origin

The club is born for the Catalina Crossing

Windy City dragon boaters and a transplanted California outrigger paddler form Outrigger Chicago to cross the Catalina channel.

2016Molokai

Road Trip to Paradise

The guys train and complete the 2016 Molokai to Oahu channel race.

2017New York

Road Trip to NYC

Brian and Jeff complete the Liberty Challenge race.

2023White Canoe

Aloha to a new boat

We retire our traditional canoe and switch to an unlimited.

2024Grey Canoe

Our 'ohana grows

Our club gains a second unlimited outrigger.

2025Blue Canoe

More members + another boat

The blue canoe is now part of our fleet. We have three unlimited canoes.

Some adventures beyond Lake Michigan

Want to be in next season's gallery?

Whether you're aiming for the channel or your first lap of the harbor, it starts the same way — get in the canoe.