Cambridge Classic Powerboat Regatta and Triple B Festival

The Cambridge Classic Powerboat Regatta is scheduled for Saturday and Sunday, May 23-24, 2026, on Hambrooks Bay off the Choptank River in Cambridge. Spectators can watch from Gerry Boyle Park at Great Marsh, where bleachers and park viewing areas face the race course.

The Cambridge Power Boat Racing Association describes the Cambridge Classic as the oldest active powerboat race in the country. The 2026 event continues a 115-year tradition of racing on the Choptank, with about 50 boats expected. Racing is scheduled from 10 AM to 5 PM both days, weather permitting, with classes including H350 Hydroplanes, 2.5 Liter Hydroplanes, Formula 2500, and Jersey Speed Skiffs.

New this year is the Triple B Festival, short for Brews, Blue Catfish, and Boat Racing, planned for Saturday, May 23, from noon to 6 PM at Gerry Boyle Park. Dorchester County's event listing says the festival will include craft brews, blue catfish dishes and other food, live music, and a Kid's Zone. The organizer's shared announcement also lists an inflatable obstacle course, craft beers from RAR and Burnish Brewery, the CPBRA beer truck, food from Hooked on Seafood, RAR's Chessie Burger Mobile, Tacos Pupusas Locas, and Red Shef, plus craft vendors and live performances by Alli Pinskey and Fantasm.

For people watching from the water, the organizer notes that boats may raft at Rooster Point and that a no-wake zone will be established from Howell Point to the Choptank River Bridge. Anyone attending by land or by boat should check the official event site for the latest schedule and weather updates before heading out.

Admission is listed as free, with a suggested $5 per day parking donation to help support the event and care for the park.