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Kicking off Oakcliff's offshore season with a Grade 5 event

by Oakcliff Sailing 6 Aug 10:39 PDT
Oakcliff hosted our August Grade 5 event © Lexi Pline

Last weekend, Oakcliff hosted August Grade 5 event, won by long-time Oakcliff match racer Doug Shannon. This was the finale to Oakcliff's Inshore Match Racing program and it saw two boats crewed by trainees who performed above and beyond.

Check out the results, photos and live streams on Facebook and website.

After racing hard on Saturday and Sunday, Oakcliff trainees hit the road to Maine for the Monhegan Island Race in the C&C 30 Flying Jenny. This will be Oakcliff's first adventure outside the bubble this year. Follow along on Facebook and check next week's newsletter for a full write up.

Alongside the C&C 30, Oakcliff graduates are preparing the Class 40 for a short doublehanded campaign. Graduates Cullen Zelenka and Brian Gallagher are splashing and delivering the boat to Newport, with the help of Rigger & Technical Specialist Cat Chimney. They plan to go on to compete in the Ida Lewis Race and the Vineyard Race.

In other news, Oakcliff is looking for volunteers for media and office work. We need computer-savvy volunteers willing to help us manage live streams remotely. We also could use some hands to help stuff and address a mailing. We have a sanitized space in 2 South Street for volunteers, with a plentiful supply of ginger beer from Regatta Craft Mixers. Email Francis for more info or to volunteer.

Have you wondered how to find people for your Quaranteam? Do you need others to help you sail a classic or a Match 40? Join our supporter Facebook group! This is a moderated, private group for Oakcliff Supporters only. Connect and sail Wednesday nights, Friday or Saturday Open Sails, or Grade 5s. Just go to "Oakcliff Supporters Crew Board" on Facebook and request to join the group.

Tight racing from the trainees to the top

Hot off a win at last week's Grade 3, Doug Shannon went undefeated at this week's Grade 4, with Jim McNally taking second and Brendan Feeny in third. But the other story is the match racing prowess of the two boats crewed entirely by Oakcliff trainees, all of whom just began match racing two weeks ago. Acorn Sam Rifkind-Brown, who gave Shannon a run for his money in the semi-finals, took fourth place, while Acorn Paloma Mannon placed sixth.

"I thought overall we sailed the course very well," said Sam Rifkind-Brown. "We also learned a lot of lessons - improving our starts and boat handling significantly and getting better at flying the kite." Oakcliff trainees competed in two graded match racing events, allowing them to get real-time experience sailing against seasoned match racers. The trainees dove into an intense training program that would exhaust anyone, but is not available to many.

"By competing in these match races with the pros, they learned how important anticipation is," said onboard coach Andres Guerra. "They also learned that in match racing, it's always important to have a plan."

Oakcliff also continued beta testing live streaming equipment, creating new media towers and allowing every boat to have at least one of their races live streamed. With these recorded live streams, competitors can learn from each other, umpires can see their calls from inside the boats, and the race committee Todd Field, Patrice Rachlin and Mimi Howard along with mark set boats Larry Kennedy and Roger Baker can see what a wonderful job they did setting the course. Read more about it here.

Flying Jenny takes off

On Monday, our C&C 30 Flying Jenny left Oyster Bay with four trainees and three Oakcliff staff: coaches Ethan Johnson and Ariel Nechemia, and onboard reporter Lexi Pline. They trailered the boat to Maine for the Monhegan Island Race, a 141 nm race.

One of the trainees, Wynn Simmons, is new to the Oakcliff bubble, having just arrived two days before departing for Maine with the team. For most of the trainees, this will only be their first or second offshore experience. With COVID shutting down most distance racing on the East Coast, this is a tremendous opportunity for them to get much needed experience.

Yes team Oakcliff is "outside the bubble" but they will still adhere to strict social distancing and mask protocols. Trainee Wes Bright took point on boat prep for this trip. He organized the crew, work list and logistics and is excited to get offshore (and visit his parents, who are graciously hosting the Oakcliff team while in Maine).

Flying Jenny is a one-design race boat designed by Mark Mills, with total length of 30.01 feet and waterline of 28.7 feet. She has carbon fiber spars and a fractional rig with 640 square feet of sail area upwind and 1,643.2 square feet for downwind sailing. She was graciously donated by Sandy and David Askew. We didn't think she was going to turn into an offshore machine.

The race starts Friday at 3pm ET. Follow the results here. Keep an eye on the Facebook Story and Instagram for updates on the team from onboard reporter Lexi Pline.

Media volunteers needed

Live-streaming brings sailing alive to fans. From the America's Cup to the Olympics the reach has been huge. Previously it has been in the hands of the professionals at ESPN or NBC Sports but Oakcliff is quickly elevating their game. From the 24 hour feeds on Oakcliff's Doublehanded Offshore to live streaming our match races we are excited about the programming we can provide. Spectators trapped at home by COVID can follow the competition, hear the onboard dialogue, and learn from the pros.

We are looking for volunteers to help us run our live streams. Since it's all done online, you can help from home. Volunteers will learn to use the Wowza custom streaming engine that is compatible with most major social medias like Facebook Live, Twitch, and Youtube. This position is great for anyone, especially high school or college students, looking to learn new computer skills this summer while cooped up because of COVID.

We have two regattas coming up later this month: a Grade 5 on August 22, and the Oakcliff International August 27-30. Each new volunteer will have two training sessions and a test run before these regattas with Development Director Francis George (the engineer behind our live streaming setup). Experience with computers is a plus, but not required.

We are also looking for volunteers to help stuff envelopes for our summer appeal letters. Oakcliff will have a sanitized area so volunteers can help out safely, or you can take them home and work on them there (while watching our Cocktail Breeze videos;-)

Email Francis at to learn more or sign up. He is happy to bribe you with food or Regatta Ginger Beer!

Splashing the Class 40

Oakcliff graduates Cullen Zelenka (the original winter sapling) and Brian Gallagher are busy putting the final touches on our Class 40 as they prepare to campaign the boat doublehanded.

Cullen and Brian, who met at Oakcliff in 2018, volunteered all winter and spring getting the boat ready and preparing and fundraising with the expert help of Oakcliff's Technical Specialist Cat Chimney. Their original plan was to race the Class 40 in the Atlantic Cup, but when COVID hit they pivoted. The boat is being splashed and delivered to Newport this week in anticipation of the Ida Lewis and then the Vineyard Race.

"We're really excited to be able to do this kind of campaigning through Oakcliff," said Cullen. Both Cullen and Brian are also looking forward to the technicality of the Class 40, as the boat has many intricate systems - perfect for two budding engineers. "This boat is one of the most technologically advanced boats in the Oakcliff fleet," said Cullen. "It's a beast."

At Oakcliff, it's never too early to get quality offshore experience. Cullen and Brian's average age is 18.5. Brian is a recent high school graduate and Cullen is going in to his second year at University at Buffalo SUNY where he is majoring in mechanical engineering. Cullen and Brian are looking forward to keeping the energy going while campaigning this boat beyond the Vineyard Race in September. If you are interested in supporting their campaign, email .

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