Black Pearl Seafood Chophouse Poker Run
The first Black Pearl Powerboat Poker Run Rally will bring a fleet of recreational and performance boats to Port Jefferson, New York, October 2–4, 2026, for a waterfront weekend of boating, live music, food and a Sunday poker run across Long Island Sound.
Hosted by Black Pearl Seafood Chophouse at Danfords Hotel & Marina and produced by the National Powerboat Association, the event will center around the Port Jefferson waterfront. Boats will begin arriving Friday before filling the docks Saturday, with the main poker run scheduled for Sunday, October 4. Spectators will also be able to enjoy the boats and waterfront activities throughout the weekend.
Saturday's activities begin at noon with registration, merchandise sales and participating boats arriving at Danfords. A 1 p.m. brunch will follow at Black Pearl Seafood Chophouse, with food and drinks available à la carte. Registration will close at 6 p.m. as the waterfront shifts into the evening welcome party and live entertainment.
Sunday begins with registration reopening at 9 a.m., followed by the final registration deadline at 10 a.m. A mandatory drivers' meeting will be held at 11:30 a.m., with participating boats scheduled to push off from Port Jefferson at noon for the poker run across Long Island Sound.
The 2026 event will feature two boat classes and separate routes. Class A, for boats from 18 to 28 feet, will travel from Port Jefferson to the Milford, Connecticut, area before returning to Long Island for a route of approximately 35 miles. Open Class boats measuring 29 feet and longer will continue farther west toward the Norwalk area before returning to Port Jefferson for a run of approximately 60 miles.
Participants will collect cards during the run before returning to Black Pearl for the afternoon poker activities. The card-pulling station is scheduled to open at 2 p.m., with the awards ceremony beginning at 4 p.m. The best poker hand will receive a $10,000 cash prize, with additional awards planned for boats, crews and event participation.
Boat registration is $399 through October 3 and increases to $599 afterward. Everyone aboard a registered boat must also hold a $25 National Powerboat Association membership. Additional poker hands will be available for $100 each.
Live entertainment will continue throughout the weekend, beginning with Tradewinds on Friday from 6 to 9 p.m. Peat Moss & The Fertilizers will perform Saturday from 6 to 9 p.m., while In The Groove will provide live music Sunday afternoon and evening.
The Black Pearl Powerboat Poker Run Rally is organized as a recreational poker run rather than a race. Results are determined by the cards collected instead of boat speed, giving participating crews an opportunity to cruise Long Island Sound, visit waterfront destinations and spend the weekend with other boating enthusiasts.