What do you expect this year?
This year feels unique—I don’t know what to expect. We had a long run of cool, damp weather, with few good days to prepare a bottom for launch, let alone polish and wax a hull. It seems as if we don’t have as many entries as we had at this time in year’s past. The race started with two boats (because that’s all it takes!) in 2009. By 2014 we had 13 boats participating. The full moon in 2015 brought a lot of sailors (we had 22 boats that year), and then 24 boats each in 2016 and 2017. To encourage new entries all the way up to race day (or until we reach 25 boats), we’re eliminating the late entry fee. The T-shirt ordering deadline has been extended to the party after the race.
Why is this the final Sippy Cup? Do you have a favorite memory from 10 years of hosting this race?
We will retire from hosting The Sippy Cup after this race. It takes so much dedication and organization to bring it all together, and we’d like to have that time to do some extended cruising again. As sailboat riggers on the Northern Chesapeake Bay, the time to enjoy our own boat here at home is limited. It’s been 18 years since we’ve sailed one of our boats on Long Island Sound or off the coast of New Jersey, and we’ve never sailed one of our own boats around the DelMarVa. As for a finest Sippy Cup memory, the best I can do is a collage—there are so many good ones. That first year, it was just us in our Venture 22 and our friend Jim and family in his Precision 23, when the wind died south of Poole’s Island in the middle of the night. We “passed” Jim by anchoring (he drifted north with the current). In 2013, four boats found themselves beating together south of Poole’s Island when the wind shifted to a close reach, inciting a 17-mile drag race all the way to the bridge. The full moon in 2015 was spectacular, and as we sailed into the night, we were serenaded by the crew of Shearwater singing a customized rendition of “Blue Moon” over VHF-71. The last couple of years there have been a couple groupings of boats that battled it out through the night—those are the best stories at the party afterward, shared with lots of laughter. Learn more and register at waldenrigging.com/the-10th-and-finalsippy-cup. Follow us!
##The 10th and final race will be run in reverse, from Annapolis to North East.
Hours: 11 a.m. to 2 a.m.
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Chesapeake Bay Sailing