2026 Columbia Yacht Club Chicago Skyline SUP Race

Registrations are now open – Only 40 spots available. Don’t miss out!

Co-hosted with Chicago SUP, the Columbia Yacht Club Chicago Skyline SUP Race will be held Saturday, May 16, bringing a focused day of racing to Monroe Harbor in downtown Chicago, set against the backdrop of Lake Michigan.

Race Formats

Competitors can choose from three formats:

• 3-mile technical race
• 6-mile technical race — new for this year, with the potential (conditions permitting) to extend beyond the harbour toward the crib or lighthouse. Final course decisions will be made closer to race day, depending on flat water and minimal wind
• Fun / short race option

With the Chicago skyline as a constant backdrop, the event blends competitive racing with an accessible format, awarding the top three male and female finishers.

About ChicagoSUP Racing Team

The Chicago SUP Racing Team – co-hosts of the event – was founded by pro SUP athlete and Coach Kirsten Marina Lefeldt, and continues to play a key role in building the local race scene.

Schedule

Saturday, 16 May

The event will be held at Columbia Yacht Club within Monroe Harbor, with the course set inside the protected waters of downtown Chicago. A detailed email with parking instructions will be sent the day prior

• 7am – 7:30am board drop / registration / check-in
• 7:45am racer meeting
• 8:00am – 3 mile race start
• 9:15am – 6 mile race start
• 10:45am – Fun / short race

Awards party will be held at the Columbia Yacht Club Bar shortly after finish

The course:

3 mile course:

3- Mile Race Course Details:

1. Start (red dotted line line)
2. Wrap around Columbia Yacht Club Dock and head north to mark A
3. Round mark A to your LEFT and head south. Slight turn at the end of the Columbia Yacht Club dock and head toward mark B
4. Leave mark B to your LEFT side and head towards the south end of the harbor
5. **1.3 Triangles at south end of the harbour**

• Leave mark C to your LEFT and continue to Mark D
• Round Mark D to your LEFT and head to Mark E
• Round Mark E to your LEFT and head to Mark C
• Round mark C to your LEFT head back to D
• Round mark D to your LEFT and head back toward mark C / North end of the harbor (can pass Mark C on either side)

6. Leave mark B to your right and head back up to mark A by the club ship
7. Round mark A to your LEFT and head back south toward the end of the Columbia Yacht Club Dock
8. Wrap around the south end of the Columbia Yacht Club dock (turning RIGHT) and finish back at the green dashed start / finish line

Note: Racers must stay in the designated harbour channels and not go in between moored boats. It is not a straight line between mark A, south end of the dock, mark B and mark C. When you are paddling south you need to wrap around the moored boats and keep all moored boats to your left. When you are paddling north you need wrap around moored boats and keep all moored boats to your right.

In Summary: START (GREEN DASHED LINE), DOCK (LEFT), A (LEFT), B (LEFT), C (LEFT), D (LEFT), E (LEFT), C (LEFT), D (LEFT), Pass Mark C, B (RIGHT), A (LEFT), DOCK (RIGHT), FINISH

6 mile course:

6 – Mile Race Course Details (plan on the course below; however, if we pivot to a race outside the harbor details will be provided closer to the race):

1.Start (red dotted line line)
2.Wrap around Columbia Yacht Club Dock and head north to mark A
3.Round mark A to your LEFT and head south. Slight turn at the end of the Columbia Yacht Club dock and head toward mark B
4.Leave mark B to your LEFT side and head towards the south end of the harbor
5.**4Triangles at south end of the harbor**

• Leave mark C to your LEFT and continue to Mark D
• Round Mark D to your LEFT and head to Mark E
• Round Mark E to your LEFT and head to Mark C
• Round mark C to your LEFT head back to D
• Repeat 3 more times – I.e. you will round Mark E 3 more times.
• The last time you round Mark C, you round to the mark to the right and head back north

6.Leave mark B to your right and head back up to mark A by the club ship
7.Round mark A to your LEFT and head back south toward the end of the Columbia Yacht Club Dock
8.Wrap around the south end of the Columbia Yacht Club dock (turning RIGHT) and finish back at the green dashed start / finish line

Note: Racers must stay in the designated harbor channels and not go in between moored boats. It is not a straight line between mark A, south end of the dock, mark B and mark C. When you are paddling south you need to wrap around the moored boats and keep all moored boats to your left. When you are paddling north you need wrap around moored boats and keep all moored boats to your right.

In Summary: START (RED DASHED LINE), DOCK (LEFT), A (LEFT), DOCK (Right), B (LEFT), 4X Triangles Below):

1.C (LEFT), D (LEFT), E (LEFT)
2.C (LEFT), D (LEFT), E (LEFT)
3.C (LEFT), D (LEFT), E (LEFT)
5.C (LEFT), D (LEFT), E (LEFT)

C (RIGHT), B (RIGHT), DOCK (LEFT), A (LEFT), DOCK (RIGHT), FINISH

Further information

Leash and PFD are required for all competitors, with the race capped at 40 participants to keep the event tight and competitive — early registration is recommended to secure a spot.

Awards will be presented to the top three female and male finishers, while a limited number of charter boards are available for those travelling or without equipment – interested paddlers are encouraged to reach out to the organisers in advance.

Register for the event here 

To find out more, visit chicagosup.com

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