Classic Cars, Fast Sailboats Mark Westport Weekend

There’s a lot going on here this weekend.

Tomorrow (Saturday, June 4) is Sunrise Rotary’s Great Duck Race (1-4 p.m., Parker Harding Plaza). There’s $10,000 in prizes (tickets are $20 each, available at the race). Plus plenty of free fun.

Tomorrow is also Shred Day (bring up to 8 paper bags or 3 boxes of bills, tax returns, medical records, etc. to the Westport-Weston Health District, 180 Bayberry Lane, 9 a.m.-noon).

On Sunday (June 5, 10 a.m.-4 p.m., Winslow Park), the Westport Weston Chamber of Commerce celebrates our 1st annual Dog Festival ($10 per person, $25 per family; dogs go free!). UPDATE: The Dog Festival has been postponed to next Sunday, June 12.

Flying a bit below that radar are 2 very intriguing events. Dragone is sponsoring a spectacular classic automobile auction tomorrow (Saturday, June 4, 6:30 p.m., 176 Post Road West).

All weekend long, Cedar Point Yacht Club hosts a OneDesign Regatta.

Believe it or not, they’re related.

Dragone and Cedar Point are cross-promoting each other. (Folks who can afford classic cars tend to also enjoy things like sailboat racing.)

Dragone director of marketing Alex Dragone stands next to a one-of-a-kind 1939 Alfa Romeo -- perhaps the most expensive automobile in the auction.

Dragone director of marketing Alex Dragone stands next to a one-of-a-kind 1939 Alfa Romeo — perhaps the most expensive automobile in the auction.

Both are driven by young people. The auction’s mastermind is 26-year-old Alex Dragone, the next generation of the famed family. Race director Samantha Parisi doubles as Staples High School’s varsity sailing coach. She brings youth and excitement to those 2 jobs.

And both events draw hundreds of people from around the world to Westport. 500 car collectors are expected to bid on 62 cars tomorrow night. Alfa Romeos, Bugattis, Corvettes, Rolls Royces and more — one dating back to 1904 — will attract bids as low as $20,000, and as high as $3 million.

Cedar Point, meanwhile, hosts more than 80 boats and 500 sailors. The schedule includes one national championship, and a Long Island Sound championship too.

“06880” will provide race photos after the final series. Meanwhile, here are a few shots from today’s sneak preview at Dragone.

A 1965 Maserati Sebring Series 2. Behind it: a 1979 Rolls Royce Silver Shadow.

A 1965 Maserati Sebring Series 2. Behind it: a 1979 Rolls Royce Silver Shadow.

New York Times automobile writer Jim Motavalli -- a Staples High School Class of 1970 graduate -- with a 1965 Sunbeam Tiger.

New York Times automobile writer — and 1970 Staples High School graduate — Jim Motavalli, with a 1965 Sunbeam Tiger.

An Allard J2$ Sphinx race car. It belong to the Sopwith family (of Camel fame). The Sopwiths were also a yachting family.

An Allard J2R Sphinx race car. It belonged to the Sopwith family (of Camel fame). The Sopwiths were also yachtsmen.

4 responses to “Classic Cars, Fast Sailboats Mark Westport Weekend

  1. Terry Eldh

    Tomorrow (Saturday) is also the DUCK RACE!

  2. Brandon Malin

    Hi Dan, just wanted to let you know you crossed out the great duck race, not the dog festival.

  3. Helen Garten

    The Great Duck Race is definitely on. Parker Harding 1-4 pm today.

  4. My bad! I’ll change it right now.