Around Islesboro Race

The Around Islesboro Race begins off the Bayside dock in Northport, Maine, and takes competitors on a full circumnavigation of Islesboro, one of Penobscot Bay's most iconic islands. The course spans more than 28 nautical miles and offers a true test of strategy, endurance, and seamanship.

Each race morning, the Race Committee determines whether the fleet will sail clockwise or counterclockwise around the island based on the forecasted wind and the timing of the tides through Gilkey Harbor, ensuring the best possible racing conditions.

In recent years, more than 50 boats have come to the starting line, creating one of the largest and most diverse races in Maine. The fleet has ranged from high-performance racers like the Dufour 50 and J/122 to classic cruising boats such as the Cape Dory 25 and Dolphin 24.

Classes

• Racing 1 (PHRF under 120)

• Racing 2 (PHRF 120 and above)

• Cruising (Non-Spinnaker)

• Multihull

• Singlehanded

Entry Fee

• $85 – Non-Members

• $75 – Northport Yacht Club Members

Supporting Youth Sailing

The Around Islesboro Race is more than just a great day on the water—it's the Northport Yacht Club Sailing School's largest annual fundraiser. Proceeds directly support our youth sailing program, which introduces more than 100 young sailors to the sport each summer. Every entry helps keep lesson fees affordable while supporting the next generation of Maine sailors.