The Around Islesboro Race
The biggest Maine Regatta held anywhere north of Portland is also the most fun. The race starts in front of the Bayside dock, circumnavigates 10 mile long Islesboro Island and returns to Bayside. The course is over 28 nautical miles as the crow flies. The direction to take around Islesboro is decided the morning of the race based on wind direction and the timing of the tides in Gilkey Harbor.
Recent years brought up to 52 boats to the starting line of all shapes and sizes, ranging from a Dumas 50 and J 122 to a Cape Dory 25 and Dolphin 24.
Racers can participate in the following Classes:
* Racing 1 (<120)
* Racing 2 (120 +)
* Cruise (non-Spinnaker)
* multi hull
* single hand
The basic entry fee is $100.
The race is held as a fundraiser to support the Northport Yacht Club Sailing School. We teach sailing and racing skills to over over 100 kids each summer. All monies raised help keep our lesson fees low.
The 2026 running will have the starter's cannon fires at 10 AM on Saturday September 5, 2025 Skipper's meeting is at 8:30 at the NYC clubhouse just off the dock. Register online at Regatta management: www.regattaman.com (see regatta management instructions below). Coffee, juice & donuts Saturday morning. Awards ceremonies are held after the race with a post race cookout and potluck lasting well into the evening. The Around Islesboro post race social is one of the great parties of the summer.
Regatta management website instructions: click on the calendar tab, then scroll to September 6 to find the Around Islesboro Race, and click the info button next to it, from there you can register.
Questions? Send an email to aroundislesbororace@gmail.com