If you happen to be in George Freer Memorial Park on Saturday or Sunday morning this weekend, you might witness the first-ever Hudson River Maritime Museum Cup Regatta pushing off from the Museum in the Rondout below. The race, presented by the Kingston Sailing Club (KSC) as part of the Hudson River Yacht Racing Association (HRYRA), heads out into the River for contests from three to eight nautical miles in length.

Regatta chairman Commodore Ian Westergren says that the direction that the race takes, north or south, depends on which way the wind happens to be blowing, which might sound like the metaphor of an arbitrary life endeavor. But these races are anything but arbitrary to sailing enthusiasts, who test their skills against the sometimes-fickle environment and each other. The KSC promotes sailboat racing and cruising, and hosts a varied program of sailboat racing on the Hudson River off Kingston each weekend from May to late October. The Club offers a challenging racing environment suitable for beginners and experienced racers alike, as well as a number of cruising and social events for its members.

This weekend’s Regatta is open to all sailors, with at least two races scheduled each day for all boat sizes and designs. At minimum, one Jib & Main (JAM) and one Spinnaker (SPIN) fleet are established for each series. Boats are assigned a handicap based on a standardized performance and handicap rating system, evening out the competition. Westergren explains that Fleets A and B are the two fastest, with the advantage of the balloonlike spinnaker sail in front, while Fleet C is for JAM-style sail designs and Fleet D is a “Fun Fleet” strictly for novice racers. The first signals are at 11 a.m. on Saturday (after a breakfast, on-site registration and a skippers’ meeting beginning at 8:30 a.m.) and at 10:30 a.m. on Sunday.

“We expect at least 25 boats to participate,” says Westergren, “from as far south as Tappan Zee and on up the River.” A limited number of slips will be available at no charge for transient boats, so reserve early. Registration and the skippers’ meeting will take place at the Hudson River Maritime Museum at 50 Rondout Landing in Kingston. The registration fee, which includes a Saturday-night barbecue for all skippers and crewmembers, plus Sunday snacks, beer and wine, is $50 in advance, $55 on race day for US Sailing members and $55 and $60 for non-members.

The HRYRA comprises six yacht clubs along the river associated with US Sailing. For more information and notice of upcoming races, cruises, courses and other social events, visit www.kingstonsailingclub.org.