The Point Betsie Trophy, sponsored by The Storm Trysail Club, is presented to the three-boat team with the best performance in the Chicago Yacht Club Race to Mackinac. First presented in 2019, this trophy is announced at the Mac Race awards at the Mackinac Island and presented to the winners at the Chicago Yacht Club Race to Mackinac Awards Ceremony at the Chicago Yacht club in the November following the race.

2019 - Team Red, White and Blue - Eagle, Providence, and Intangible - Shawn & Jerry O'Neill, Greg & Gerry Miarecki and Tom Falck
2022 - Team Red, White and Blue - Eagle, Providence, and Intangible - Shawn & Jerry O'Neill, Greg & Gerry Miarecki and Tom Falck
2023 - Team Red, White and Blue - Eagle, Providence, and Intangible - Shawn & Jerry O'Neill, Greg & Gerry Miarecki and Tom Falck
2024 - Team Bayview Yacht Club - Pterodactyl, Natalie J, Fast Tango - Mark Symonds, Philip & Sharon O'Niel, III and Tim Prophit