Keelboats will join the Philadelphia skyline on Saturday, May 25, for a long-dormant competition that’s finally ready to return.
Sailors from local clubs are preparing to race in the Philadelphia Cup Regatta for the first time since 2016. The competition has traditionally drawn over 100 boaters to the Delaware River but had paused in recent years. Now, the city’s own Liberty Sailing Club is bringing it back.
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The race will be divided into three fleets, categorized by the type of boat. The vessels in two of those fleets will have a typical sail setup with a mainsail and foresail, but some will use a spinnaker, a large and lightweight sail that puffs out like a parachute for downwind racing. Dinghies, smaller boats that can be manned by one or two people, will also race. All competitors will gather early to check into the race and meet before the first gun is fired at 10 a.m. on May 25.
Caitlin Youngster, a skipper with Liberty Sailing Club who is sailing a spinnaker boat in this year’s regatta, says the club was eager to resurrect the race, especially after an influx of new members who had never participated. The competition was not discontinued due to a lack of interest but, as far as she can tell, an overwhelming amount of logistics.
“It’s a lot of work to host something like this,” she said. “Our club is all volunteer-run, so we don’t have a full-time staff. It’s taken a year of planning just to get it going again.
“But I think the groundwork has been laid now and some of the kinks worked out. And so I think we have a really good foundation now to continue doing this on an annual basis moving forward. That’s our plan.”
Awards will be presented at 6 p.m. at the Independence Seaport Museum, with a reception to follow aboard the Gazela, a historic fishing vessel owned and maintained by the Philadelphia Ship Preservation Guild. For those who want to watch the event, Youngster recommends the Penn’s Landing promenade, Spruce Street Harbor Park, Cherry Street Pier or Race Street Pier. Adventurous bikers or pedestrians will also have a great view from the walkway of the Benjamin Franklin Bridge.
Youngster sees the regatta as a way to honor the waterfront’s unique place in the history of Philadelphia and the Lenape people who lived along its banks. But she also hopes it can serve as an entry point for amateur sailors hoping to hit the sea for the first time.
“I think the community of people who sail in Philadelphia are really special in a way,” Youngster said. “It’s very approachable, it’s very welcoming. There’s a good sense of camaraderie. It’s not pretentious. And so I think for people who are looking to sail in a way that is sort of competitive but still enjoyable and welcoming … this is a really good place to be doing that.”
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