Charles Island SUP Cup 2026
By Ellison Smith, USA SUP Vice President
Photos courtesy: Harper Photograph
Day 1
NEW this year! Time Trials
One half mile each way around a buoy from the beach. Easy right? Not so much, add in some stiff crosswinds and it's a real challenge! Thankful to be have trained in such conditions though not yet hitting my full stride this season, I was able to complete the challenge in a reasonable amount of time. Taking what I could, when I could without taking a swim and having confidence in my training. Challenging yourself is always very rewarding after you've finished the task. Got to see some of the best show everyone how it's done. Having a bonus day with everyone made the weekend extra special!
Day 2
The Charles Island SUP CUP holds a very special place on the calendar and in the hearts of many paddlers. It is a uniquely cultivated spectacle shaped by some of the most passionate minds in the sport. Bill Harper of Harper Photograph, Joe Galiatsatos and Bryan Hughan capture the essence of the event in all of it's magnificent glory. Their artistic use of drones and cameras is uncanny. The recordings serve to bring the stoke to those watching on their devices from wherever they may be. Walnut Beach shines bright as the water from the Long Island Sound reaches the shell filled beach. Milford Mayor Rich Smith recognizes the significance of the event and it's lasting impact on the community. The 11th anniversary of the race, as in previous years, brought participants from up and down the east coast, ranging from Canada all the way to Florida.
The competition was stiff, but that didn't keep any others. For some it was the first or second entry ever in a competition, for it's not all about that, but more so the community element and shared stoke that SUP brings to countless souls. The course begins with a running start from the beach, ornamented with the home flags of every participant, to the first unique element. A golden buoy which holds a special prize for the first reach it. Paddlers continue on to Charles Island, the race's namesake. The 15 acre island is named after English settler Charles Deal who bought it in 1657. From there, it's back to the beach for the second element, a turnaround on the beach before heading back out to a large buoy. A step back turn there then it's on to the final stretch. Back towards shore, rounding another buoy and parallel to shore, prior to a series of three technical turns right before running back onto shore and across the finish. Spectators love the action as they cheer loudly for all but a little louder for their favorites.
One cannot say enough positive things about race director and Surfrider Foundation Connecticut executive Jack Egan and everything he's done uplift the sport and the community. He is deeply invested and puts forth an incredible amount of effort. He takes care to engage and listen to anyone about SUP. Thank you Scoot & Paddle for continuing to support the event year after year and ensuring it continues. A staple in the town, they provided rentals to anyone who wished to get out and enjoy the many benefits of paddling. Cheers to Athletic Brewing Company for providing the non-alcoholic awards to quench the the thirst. Just as big a thanks to everyone who donated their time in making it happen on both days. I'm forever grateful to Bob Fournier for welcoming me into his home during my stay. I was treated royally as he invited me to dinner with his family and chill time in the pool. Haven't been yet? Do yourself a humongous favor and get on it ASAP!
