St. Michaels Wednesday Night Racing hosts races on Wednesday evenings. The races
run from the first Wednesday in May to the first Wednesday in October
giving us about 22 evenings of fun!
Sep 17, 2026
Results from 9/16
Sep 10, 2026
Sep 8, 2026
Still 20 minutes earlier
Remember, we start 20 minutes earlier tomorrow.
Warning for the cruising class at 5:35 PM.
Sep 2, 2026
Results from 9/2
Well, the wind wasn't what was promised, but we made up for it with a strong current! Nothing could be more fun than fighting the incoming tide to make it to Deep Water Point.
At least it was a cool night with a nice sunset.
Thanks to the log canoes for coming out. It was fun to see three on the starting line. It was also great to see other competitors come out to race for the evening. When did we last see Roger race the Lightning?
Here are the results:
https://nextsailor.com/app/scoring/view_results/1266/3356
Thanks for coming out to remember Mr Jimmy.
Sep 1, 2026
20 minutes earlier tomorrow
Remember, we start 20 minutes earlier tomorrow.
Warning for the cruising class at 5:35 PM.
Aug 30, 2026
Round the Island Race on September 2nd
Yay! September 2nd is the James H Wilson Round the Island Race. It's our annual crazy race when we remember Jimmy Wilson.
We race out of the Miles River, sail around Herring Island either direction, and then back to the finish. It's usually about 6.5 nm. The starting line is perpendicular to the course to the first mark. That means we're likely going to have a reaching or downwind start.
There will be log canoes out there starting with the cruising class. They are generally less maneuverable than you, so be nice. They are in their own class, so there is no reason to crush them at the start.
There are special sailing instructions. You can see the sailing instructions here:
https://drive.google.com/file/d/150t7vwes-F5euzEc-KEefhha3nhQOCDV/view?usp=drive_link
What is up with this crazy race?!? Well, Fun. This is supposed to be a fun race in a different format. This race also has a long history with the log canoe fleet (it used to be called the Bigelow Cup) and with CBYRA. Mr. Jimmy loved this race and ran it every year for a long time. There are special trophies for this race.
We all miss racing against Mr. Jimmy, so we run this race in his memory. Come out to have fun! We might see some other competitors who typically do not come out for Wednesday nights. It's all good. New boats and log canoes mean lots of people who don't understand the rules like you do. Breathe deep and sail fast.
Aug 29, 2026
Fall is here - we're starting earlier
That's right! We start races earlier after September 1st - 20 minutes earlier!
The starts are earlier - you should leave the dock earlier - you should leave work earlier!
Every Wednesday Night Race from now to October.
Who would do that? Well, we're running out of daylight. We need the time to get in a race. We try to finish everyone before sunset, but sometimes it doesn't work. Remember to use running lights after sunset.
We talk all about this change in the SIs:
https://drive.google.com/file/d/1hhMvvq1jbIWWaiQwGPWq3mWsz8Wu9vZo/view?usp=drive_link
Also!
September 2nd is the Jimmy Wilson Race. There are special sailing instructions for the race. You can see them here:
https://drive.google.com/file/d/150t7vwes-F5euzEc-KEefhha3nhQOCDV/view?usp=sharing
More info to come
Aug 28, 2026
Aug 11, 2026
Guest Skipper night
Remember that tomorrow (8/12) is Guest Skipper night. Find a friend to come drive your boat for the evening.
Let's hope for good wind!
Aug 6, 2026
Jul 30, 2026
Results from 7/29
Jul 23, 2026
Jul 16, 2026
7/15 Results
Yay Wind! Boo heat.
Here are the results.
https://nextsailor.com/app/scoring/view_results_fleet/1266/3110
Jun 29, 2026
No racing 7/1
Remember folks - there is no racing on July 1st.
I think it's a good time to do a practice run on your grill game. No 4th of July is perfect without a properly grilled hamburger. You'd better start practicing!
Jun 18, 2026
Results from 6/17
Sorry, I was distracted on Thursday. Here are the results from Wednesday Night:
https://nextsailor.com/app/scoring/view_results/1266/2949
Nice wind!
Jun 4, 2026
Results from 6/3
Finally! Wind, but not tons of wind. At least we got to go sailing.
Here are the results:
May 28, 2026
May 21, 2026
No races 5/20
May 16, 2026
Herring Island Sailing Fleet 2026 Schedule
Are you interested in some weekend sailing on the Miles River? Here is the schedule for Herring Island:
