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Great Fun on the 2019 Cruise

Thirteen boats participated in this year’s Annual Cruise. Featuring a nice mix of old favorites and new-to-many, participants enjoyed great company, generally good weather and the occasional navigational challenge to keep things interesting.

The cruise started officially on Sunday, August 11 with a kick-off dinner in Westport, MA. But given the distances involved, many choose to augment the experience with some informal get-togethers along the way with several opting to lay over in Jamestown Saturday evening.

Despite numerous dire warnings from the various cruising guides, our group found the Westport channel well marked and the river current manageable. Only one of our members opted to burnish the bottom of their keel in preparation for the next day’s race.

Once ashore, the group migrated 10 miles inland to Weatherlow Farms, a genuine working farm. The setting proved spectacular, the food outstanding and the company, again, terrific.

Larry Huntington regaling the crowd with the reminder of the warning he'd made to Karin nearly 40 years ago!


The first day of official cruising was Monday which was also Race 1 for the sailboats. The course: Westport Harbor to Sow And Pigs lighted buoy off Cutthyhunk , around Penikese Island to the finish off the east entrance buoy off Cuttyhunk Harbor. The conditions were spectacular and featured some close racing. The first four boats finished within 45 seconds of each other! Who knew the race committee would have to use audio to record finishes on the Annual Cruise?

Vantage, Courage, Quality Time and Evenstar finishing with 45 seconds of each other!

Dining ashore was at-will with many opting for Cuttyhunk’s famous seafood offerings while others enjoyed a bonfire on the beach and others dined aboard. And it was in Cuttyhunk’s inner harbor that we had our first sighting of an exceedingly rare giant pink flamingo.

Day Two was to feature a trip through Quicks Hole and a short jaunt over to Menemsha (Martha’s Vineyard). The forecast was not to everyone’s liking so some decisions were made to stay in Cuttyhunk or go up to Vineyard Haven. Most though, wherever they landed, ended up at Gus & Jill Dupont’s for drinks where they enjoyed some wonderful hospitality among a gorgeous setting with wonderful gardens. The evening eventually devolved into a giant pizza party!

Huzzah was the only boat outside in the Bight and Karin happily reported back that the soothing sounds of waves breaking on the nearby beach made for a peaceful evening aboard.

Day Three involved a 10-12 mile trip up to Lake Tashmoo. This location was chosen to test the nerves of the blow-boaters (or anyone with more than 5’ feet of draft). Cruise organizers had been assured the inlet had been dredged sufficiently to allow sailboats to enter the lake. Let’s just say a few more of our boats opted for a last-minute keel rub ahead of Race Two. In the end, nothing that a few more rpms couldn’t overcome.

Once inside, participants were treated to a thoroughly lovely setting and ultimately, a clambake on the beach. The modestly less-than-perfect weather earlier in the day appeared to have scared off the crowds despite the fact the sun had come out so the Indian Harbor contingent had the beach virtually to themselves. Fresh lobster, oysters, clams and corn all prepared for us within a dinghy ride of our boats.



Day Four we transited Woods Hole to get to Hadley Harbor. A race was attempted but the less said about that the better.

Hadley Harbor is well known to be among the most beautiful cruising spots in New England. Let’s just say we weren’t disappointed. Boats rafted together in various combinations and all joined in the Huzzah/Old Fashioned/Lazy Train raft-up for drinks and nibbles. Some exploration was done via dinghy with some areas proving to be a challenge for even the largest outboards (while there’s little current through the anchorage, it can be substantial where it gets shallow and the channel narrows).



Day Five had the fleet heading to South Dartmouth for our closing dinner at New Bedford Yacht Club. Another race was run that proved a test of one’s patience but since you had to get east-to-west, several stuck it out and “enjoyed” it to the end. Bit of a drift-fest to say the least. Fortunately, dinner ashore, outdoors and under a tent was wonderful. Post-cruise commentary was provided by Jonathan Nye and Jamie Cummiskey.

On Saturday, we enjoyed what could become a new tradition. Before heading off, the fleet was treated to brunch at Mark & Heidi Silverstein’s remarkable home in South Dartmouth. It was clear people had mixed feelings about leaving the party versus knowing they had to start making their way home. In all, a wonderful way to cap off a special week.

Just some tidbits from the Cruise:

  • A most unusual laundry offer.
  • Whatsapp proved useful keeping everyone apprised of the goings on.
  • One couple heard saying “You were not much help with the anchor, but you made up for it at cocktail hour”. It’s widely believed this marriage remains intact.
  • The revenge of the celery stalkers.
  • Huzzah taking soundings entering Lake Tashmoo (available on the club’s Facebook member page). Note the shallow water alarm (heard going off) is calibrated off the bottom of Huzzah’s keel!
  • Ginger, everyone's favorite.


Additional pics on the home page and Yachting gallery soon.