10/14/10 8:30pm

Strap on your running shoes and don’t forget to stretch — the 11th annual Shelter Island 5K Run/Walk is just around the bend. The race starts on Stearns Point Road at 10 a.m. on Saturday, October 16. Runners will gather on Crescent Beach before the race for registration. Registration after today costs $30, but there’s still time to register online for $25 at shelterislandrun.com. Children 14 and under register for $10. Currently there are just over 300 runners registered, but Race Coordinator Mary Ellen Adipietro wants you to be one of the additional 150 runners she hopes will sign up.

Race participants will receive a T-shirt, goody bag, a free ticket to a raffle and a post-race therapeutic massage and barbecue. (Non-participants can join the barbeque for a nominal fee.) A stretch clinic run by Oscar Gonzales will also be provided, courtesy of Moussa Dramé. This year, every participant will receive a medal, sponsored by Dr. Frank Adipietro. Race coordinators will run a free shuttle from North Ferry to the staging area between 8 and 9:15 a.m. and back to the ferry until 12 noon.

This fall’s race is dedicated to Patty Conway, whom Ms. Adipietro described as always being a “good friend of the race” and contributing a free golf lesson as a raffle prize year after year. She lost her battle with cancer and passed away the day after the race in 2009.

In its 10-year history, the 5K has raised over $200,000 for the North and South Fork Breast Health Coalitions. This year, the money will be split evenly between the North Fork Breast Health Coalition and the newly-formed Coalition for Women’s Cancers at Southampton Hospital, whose focus is not just breast cancer but also other women’s cancers.

The raffle following the race will benefit Lucia’s Angels, an organization dedicated to helping patients with late-stage women’s cancers and their families. You must be present at the raffle in order to win a prize. Ms. Adipietro hopes the race will raise a combined $18,000 to $20,000 for the Breast Health Coalitions and Lucia’s Angels.

For more information, or if you’re interested in volunteering, call Ms. Adipietro at 774-9499.

10/14/10 4:58pm

A strong breeze carried these three Herreshoffs through their upwind leg in just eight minutes.

It’s a true sign of the end of the sailing season: well over half the moorings in Dering Harbor are now empty. But that didn’t stop seven sailors in five boats from participating in the Shelter Island Yacht Club’s Herreshoff 12 1/2 channel race this past Saturday. Sailors started off North Pier with a strong westerly breeze and twice sailed back and forth between Dering Harbor and channel marker N10, along the ferry channel.

Bruce and Susan Brewer took the win in their boat Spray, followed by Peter Dinkel in Nebraska. Denny and Ellen Clark crossed the finish line in Lulu Belle off North Pier third and Chip Luddecke finished fourth in Joan and David Wicks’ boat, Sweet Dream. Dona Bergin was over the starting line early but still completed the course for fun.

“It was nice, we had a beautiful breeze,” said Ms. Brewer.

Later that afternoon, the Yacht Club held its decommissioning ceremony, followed by dinner and dancing.

10/14/10 4:37pm

The crew of Instant Karma prepare for the start of Friday’s 90-mile round-trip race to Block Island.

“It was a sail-maker’s dream — many, many spinnakers got blown apart.”

This year’s Greenport Ocean Race, according to race organizer Peter Rowsom, was indeed a thrilling adventure. The 90-mile race from Greenport to Block Island and back didn’t just test the sailors’ skill but also their sailboats’ physical limitations.

The competition began just after 1 p.m. on Friday, and the breezy conditions were enough to intimidate some — 4 of the 27 registered boats never showed up to the starting line just off Preston’s dock in Greenport.

Peter Reich, sailing on James Eklund’s Jul Bocken, estimated that seas were 10 to 12 feet halfway between Montauk and Block Island and that winds throughout the race were in the low- to mid-30 knots. Rowsom, who raced on Errant, said the crew clocked one 42-knot gust and at one point got the boat up to 17.5 knots, “the fastest the boat has ever gone.”

Reich explained what it was like out in the open sea: “I was sitting on the leeward side getting hit by spray from every wave, but it would dry from the wind before the next wave. After a while I touched my face and it felt like cement — so much salt caked on there.”

He added that at one point the boat “death rolled,” a near-capsize while sailing downwind with the spinnaker flying — the spreaders, which are outriggers on the mast, were almost in the water. The stress on the rig from the breeze snapped two of Jul Bocken’s pulley blocks and tore her spinnaker, and the boat lost power to her navigation lights.

Reich estimated that six boats ripped their spinnakers. Six boats were forced to drop out during the race. One boat, Kialoa V, lost its steering while cruising along at around 20 knots under full sail, spinnaker included. The crew jury-rigged an emergency tiller and was able to get back to port unaided, though they had to drop out of the competition.

Despite the challenging conditions, most of the boats — Jul Bocken included — completed the event. This year’s Greenport Cup, awarded to the first boat to cross the finish line, went to a 62-foot catamaran named Zenyatta, skippered by Nils Erickson. Zenyatta finished in 9.35 hours at 10:25 p.m.

The most sought-after award, the Brooklyn Ocean Challenge Cup, found its way from that New York City borough to the North Fork in the early 1950s and is given to the boat in the spinnaker division with the best corrected time under Performance Handicap Racing Fleet (PHRF) rules. It was awarded to Dark ‘n Stormy, a J-105 skippered by Michael LaChance, for the third year in a row.

A third award, the Shelter Island Team Trophy, goes to the three boats from recognized clubs that have the best combined corrected time. This year it was awarded to Shelter Island Yacht Club for the performances of Barleycorn, skippered by Brendan Brownyard, Errant, with Larry Landry at the helm and Better Than… skippered by Gosia Rojek.

Though some would say it sounds terrifying, Reich says competing in the race in such challenging conditions is a thrill. “It’s exciting, you get psyched up.” But after so many hours, the trial starts to wear on the participants. “It’s pretty exhausting, takes a lot of concentration at the helm — after it gets dark you can’t see the sail … You start thinking about a warm shower and a warm bed, and start to wonder, ‘what am I doing out here?’” he said with a laugh. “But you keep going. That’s part of the fun, I guess.”

Originally called the Brooklyn Ocean Challenge, the race was revived in 2008 after a lull of nearly 30 years, and is sponsored by the Chinese Yacht Club of Greenport, Greenport Village and the Old Cove Yacht Club of New Suffolk.

It’s open to sailboats that are at least 21 feet long and have a PHRF rating of at least 200. Most boats carry a crew of about five.

In 2008, the best time — 8 hours, 54 minutes, 29 seconds — was posted by Mr. Brownyard’s Barleycorn. But his adjusted time came to over 10 1/2 hours, giving the Brooklyn Cup to Mr. LaChance’s Dark ‘n Stormy, which posted an adjusted time of 10:07:49.

In 2009, Mr. Brownyard won the Greenport Cup again with a time of 9.9 hours. But with a corrected time of 11.68 hours, he narrowly lost the Brooklyn Cup to Mr. LaChance whose adjusted time was 11.5 hours.

The original Brooklyn Ocean Challenge began in 1904 at the Brooklyn Yacht Club. In 1905, then-commodore William Randolph Hearst contributed the cup as the prize, proposing that the first yacht club to win three successive races should keep the cup permanently. Longtime East Hampton resident Stuyvesant Wainwright, who passed away only recently, won the race for his club in 1920, 1922, 1923 and 1924. But Mr. Wainwright decided the cup should remain with the Brooklyn Yacht Club and that winners should receive a replica.

The annual races continued until 1937, followed by a 17-year hiatus, and the cup was erroneously reported to have been destroyed in 1952 in a fire at the American Yacht Club in Rye.

In fact, the cup was in the possession of James Heatherton of Shelter Island, the Brooklyn Yacht Club’s sole surviving member. He presented it to the Chinese Yacht Club in Greenport, which revived the Brooklyn Ocean Challenge in 1954 and continued it until 1979.

According to Andrew Rowsom, racing resumed in 2008 at the suggestion of sailor Jim Ryan, who easily won support from other sailors around the East End and from the Village of Greenport.

The village saw the race as a way to help extend the summer season and bring business to Mitchell Park Marina, Mayor David Nyce said at the time.