March 2026

Sail Chicago Tell Tale
Issue 3: March 2026
From the Editor:

It’s March! That means it is almost time to sail. Ok, almost, almost. But now is a great time to plan your Sail Chicago participation! So consider signing up for maintenance, visiting the boatyard, and meeting some new sailing buddies at Sail Chicago’s first 2026 social event. Stay warm and see you on the water..soon…

Meighan Depke, Editor

Boatyard Open House

Interested in learning more about offseason maintenance? Or maybe just to see what the boats look like out of the water? Come find out! Join the maintenance teams at the Boatyard Open House at the Canal Street Marina. The teams will be giving tours, holding knot demonstrations, and allowing sneak peeks of Sail Chicago’s new maintenance tracking system. Coffee and snacks will be provided. 

Where: 2059 South Canal Street 

When: Saturday April 11, 10–12

Class Registration Begins in April

A new season of sailing is almost here, and it begins with the rollout of our schedule of classes! New and returning students can find information about the class rollout and registration timeline on the Sail Chicago website. Our class schedule will post the last week in March. Lottery signups will open on April 1, and individuals in the lottery will be notified of their registration window no later than April 14. Please carefully read our Class Registration and Cancellation Policy for all the information you need to know about selecting classes and meeting our prerequisites.

Key Dates for 2026 Learn-to-Sail Course Rollout:

General Registration Lottery opens for signups, April 1
— Group 1 Pre-Registration begins April 1 at 10:00 am
— Group 2 Pre-Registration begins April 5 at 10:00 am
— General Registration Lottery closes to signups on April 10 at 11:59:59 pm
— General Registration opens with Group 3 on Wednesday, April 15 at 10:00 am
— General Registration continues through April or until classes fill
Remaining Learn-to-Sail seats will open to the public on Friday, May 1 at 10:00 am.

If you have never taken a class with Sail Chicago before, remember to sign up for the General Registration Lottery April 1-10. If you do not sign up by April 10, you will have to wait until May 1 to register for classes.

From the Volunteer Team

Hello Sail Chicago! Volunteer reporting for 2025 is complete, service time is set, and status is updated on member landing pages when logged into my.sailchicago.org. Sailing credits for those in leadership and management positions will be added by the end of March.

Looking ahead, there are many opportunities for service time in 2026 that take advantage of skills you already have, or teach you something new. Our volunteer site shows all positions available for 2026. If you indicated an interest in continuing in your 2025 role, you've probably been re-assigned to that position. Please check the data hub for your current assignments.

NEW IN 2026: VOLUNTEER LEVELS!

To help guide volunteer positions that best suit skills and experience, the Volunteer Team has developed levels for each position. The volunteer site now lists all the available opportunities in order by level. Here's what those levels mean:

Level 1 — New to Sail Chicago: For new members and those looking for an entry-level commitment. No skills or experience are neededl; these are show up and help positions. Experienced members will be available for guidance. Many of these “jobs” will place members on a mailing list for opportunities that open as needed. Examples: River trips, boat teams, mast stepping, social

Level 2 — Some Experience Required: These positions require a year of membership to Sail Chicago or specific skills that are needed for the organization. Any job that requires a skipper is at least level 2. Examples: Deputy boat managers, deputy maintenance team leads, some IT jobs, MCO Skipper, Tiller Time Skippers

Level 3 — Skilled or Oversight Positions: These positions require 2 years of membership and may require specialized skills or a license/credential and may include direction of other members. Positions frequently involve deadline oriented tasks that ensure the organization operates smoothly. Examples: Higher-skill IT jobs, bookkeepers, instructors, boat managers

Level 4 — Program Directors: These members lead our programming. Examples: Licensing and insurance coordinator, lead instructor, social director, IT director

Level 5 — Board of Directors and Officers

Remember, if you fail to meet your 2026 service time requirement, either because you didn’t volunteer for a position or you failed to fulfill the responsibilities of the position, you will be required to pay a service time waiver for the 2026 season before you can renew your membership in 2027.

There are plenty of volunteer opportunities available each season, and many of them can be carried out in just a few hours each month. If you're not sure where to start or what you'd like to do, reach out to the volunteer team at volunteer@sailchicago.org.

Maintenance Volunteers Wanted

Sail Chicago’s maintenance program has already begun work for the season and is looking for volunteers! Openings include formal seasonal positions (winter, spring, summer, and fall) as well as general activities like boatyard work, mast stepping, and river trips. Maintenance is a fantastic way to learn about the boats and no experience is required. Most positions are limited to a defined time frame and some can even be performed remotely! Check the Volunteer section on My Sail Chicago for current postings, or join #colgate-maintenance-general on Slack to see when teams are working in the yard.

If you have any questions don’t hesitate to reach out to James Wyeth and Ben Carls on Slack or by email at ben.carls@sailchicago.org /james.wyeth@sailchicago.org

Bridge Season Coordinator Wanted

Sail Chicago’s maintenance program has a few new positions this season and one for which we are actively recruiting is Bridge Season Coordinator. This high-level leadership role will oversee river trips, mast stepping/unstepping, and commissioning/decommissioning. This position requires maintenance experience and applicants should be comfortable with some hands-on boat time at the start of each season. The role is primarily planning and coordination, and only active in spring and fall when boats move between the boatyard and harbors. No boatyard or in-season work is required.

If you are interested, please contact james.wyeth@sailchicago.org and ben.carls@sailchicago.org. A full job description can be found on the volunteer portal.

Social News

Our first social event of the year is only a week away. Meet us at Big Mini Putt Club Lakeview for an exciting pre-sailing season activity! Dust off your skills and kick things off with a mini golf event you won’t want to miss.

When: Thursday, March 12, 6–8 PM

Where: Big Mini Putt Club, 3655 N. Halsted St.

Who: Free for Sail Chicago members

Registration is required and spots are limited. Your registration includes two hours of unlimited mini golf. Drinks will be available for purchase.

Register here

In Memoriam – Jay Owens

On Sunday, February 8, Jay Owens passed away peacefully in his Colorado home, surrounded by friends and family. He died from complications that arose from acute leukemia.

Old timers in Sail Chicago will remember Jay as a founding member of Sail Chicago. He was elected to its first Board, where he served for several years. He also served as the organization’s bookkeeper for well over fifteen years and was a member of the Cruising Program’s maintenance team. He liked nothing better than going out on weekly maintenance sails on Sail Chicago’s first cruising boat, Emotional Rescue, and later on Priorities. He will be missed.

Merch for Sale

Check out our cool line up of Sail Chicago merch. T-shirts, polos, jackets, fleece, and hats from top quality vendors are all embroidered with our burgee logo. Take pride in Sail Chicago! Gift cards are available in increments of $25.00.

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View previous issues of The Telltale

Sail Chicago Mission Statement  |  Member Benefits  |  Fleet Locations  |  Member Log In  
Member Registration  |  Sail Chicago Rules and Regulations  |  Board Meeting Minutes
Instruction  |  Sailing Weather

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April 2026