Fun-loving, Challenging Helly Hansen Regatta Annapolis 2025
(Annapolis, MD)- The first, and largest regatta of the summer on the Chesapeake Bay for the past few decades has been the Helly Hansen Regatta Annapolis. Hosted by the experienced veterans at Annapolis Yacht Club and their partners (Eastport Yacht Club and SSA), the fleet of 240+ boats was treated to exceptional, professional race management over the three days of the regatta, with some fleets experiencing a packed agenda of up to nine races! Remarkably, J/Boats accounted for over 75% of the fleet! Here’s how it all went down over the three days.
Day One- Friday
With four race circles hosting multiple classes, clear air didn’t come easily either, especially on the southernmost circle with the J/105s, J/80s, J/70s, and J/88s— more than 80 boats racing up and down the course.
Cate Muller-Terhune’s CASTING COUCH, last year’s overall winner of the J/70 class and the regatta, has proven in the past that they know how to manage the traffic and came away with two race wins and a second to set up a 4-point lead on Alec Culter’s team on HEDGEHOG.
John Bell’s team on HIWASSEE is sitting pretty with two race wins, but Andy Graff’s team EXILE, a perennial rival to the HIWASSEE crew, is only 5 points back (winning with a 2-1-1), but Andy Graff’s EXILE is only 5 points back.
Equally close in points are the J/105 leaders, with Ben DuPont’s WARBRIDE winning the last race to end day 2 points atop Bill Zartler’s DEJA VOODOO.
Over on the Division 2 course, Jeff Hayden’s team on the POLAR EXPRESS leads the J/22s, Dan Watson’s AVITA is top J/30, and Michael Baugh’s J/29 PERSEPHONE is tied with Glenn Smyth’s SHADOWFAX.
Day 2- Saturday
Winds were moderate from the south, the current was ebbing most of the day, and the sun was shining again—all in all a perfect day for the competitors that have been racking up races over the past two days.
James Sagerholm’s legendary J/35 AUNT JEAN executed a similar strategy from the start, promptly tacking after crossing the line and beelining to the right, which ultimately set them up for a second on the day and put them only a point behind Time Machine going into Sunday’s second distance race.
The J/24s got their series underway on Saturday. Pete Kassal’s SPACEMAN SPIFF won two of five races to finish the day with a 3-point lead over Pat Fitzgerald’s RUSH HOUR.
Out on the jam-packed Division 3 circle, with the J/88s, J/80s, J/70s, and J/105s— the intensity of the respective fleets certainly went up a notch in the moderate winds and busy race course. No one got away easy; every point was a battle, said Andy Graff on the J/88 EXILE. His team’s 1-2-1 scoreline came with its challenges.
“We had a good day—we were going pretty good, felt fast, and made some good calls— but it’s all pretty close and the next two boats are just barely behind us.”
Indeed, John Bell’s HIWASEE is only 3 points back, and Lindsay Duda’s SIN DUa won a race to keep themselves well within striking distance of the lead.
EXILE and the J/88s have the fortune of being the first start on the circle, which gives them an open course on the first beat, but a different strategy was required for the second. “The second beat is a bit harder to cross back through the middle,” Graff says, “so when we picked a side on the second beat, we really had to stick with it. Choices are more limited on the second.”
Cate Terhune Miller’s CASTING COUCH kept its consistency alive with three top-five finishes and now sits on a 4-point lead over Paul Green’s PROGRESS, which won two races to keep the series plenty tight. The two teams have built a comfortable margin over the rest of the fleet with the potential for two more races on Sunday ahead of an approaching cold front.
In the J/80s, Mike Beasley’s BLACK SHEEP found itself at the back of the fleet in the morning’s first race, posting an 18th before winning the next and finishing the day with a second in the last race. Only 5 points now separate BLACK SHEEP and Warren Flannery’s team on FESITY, which won the final race. Sarah Alexander’s MORE COWBELLS, however, is third overall, only 1 point in arrears, which should make for an exciting final day for the J/80 sailors.
Ben duPont’s WARBRIDE maintained its lead in the 22-boat J/105 fleet, but only by 4 points over Ray Wulff’s PATRIOT. Wulff’s squad won the day’s first race and followed that with a second in the next, but a 14th in the final kept them from snatching WARBRIDE’s lead. Like the J/80s, this series will no doubt come to the final race on Sunday.
Michael Baugh’s PERSEPHONE put three wins on the board and now leads the J/29 fleet by 9 points, and Jeff Hayden’s team on the J/22 POLAR EXPRESS has 4 points on Brad Julian’s YARD SAIL.
Day 3- Sunday
“Race for every point” is a phrase heard often at regattas, and that was certainly the takeaway for many teams at the regatta. Three days packed with races allowed every sailor to make good on that cliché, especially the team on Andy Graff’s J/88 EXILE, which won in its fleet after a stressful two-race final day. Their class win, on a tiebreaker, earned them the regatta’s overall title and a berth at the Regatta Series championship in the BVI in October.
With a strong southerly on the final day, EXILE was sitting on a marginally comfortable lead over John Bell’s HIWASEE, and Graff intended to sail a clean race and stick to what had been working for them over the previous two days.
That plan quickly unraveled in the first race.
“It wasn’t how I planned on things going when I woke up this morning,” Graff says, “but we got out to the course and the breeze was like 17 knots. We expected more wind and made the poor decision to go to the small jib, and also got caught with the rig too tight and with chop the way it was today. That was a tough spot to be in when it dropped down to 8 knots. We just couldn’t get the wheels going through the chop.”
EXILE finished sixth in the 8-boat fleet, and HIWASEE won the race, putting them on top.
Then came HIWASEE’s drama. In the final start, Bell says, there was a miscommunication on the timing, and they found themselves OCS, clearing out to restart, and chasing down the rest of the fleet.
Battling back to earn point by point, at the beginning of the second beat, Bell realized their headstay had come off. They quickly attached a spare halyard to secure the rig and continued to sail the race. “We didn’t do so hot on that last race, but we needed to beat one boat to keep first place. When we got the one point we needed we we were pretty pumped.”
Pumped until they later learned that another boat had been OCS as well, but wasn’t scored as such. When that boat was later given an OCS, the scores shuffled once more, this time in favor of EXILE, which finished fourth in the final race and was ultimately declared the winner on the tiebreaker.
“It was hard,” says EXILE’s tactician Kris Werner. “I was admittedly pretty dark after the first race, because it felt like we just made a really poor decision with the jib. We finished that race and regrouped. The last one was tough, too. We had a pretty good start, we were kind of right in that top three for most of the race. We fought till the very end, we had almost a photo finish with [Iris Vogel’s] DEVIATION. That point was critical.”
J/80 Class
A similar fate awaited Mike Beasley’s team on the J/80 BLACK SHEEP, which went into the day with a comfortable lead in the 21-boat fleet. In the first race, they posted a 13th and then a ninth in the second race.
“In the first race, we got trapped off the start line and made it hard for ourselves,” Beasley says. “The right came in…we were protecting the left.”
In the final race, they were 1 point out of first behind Warren Flannery’s Canadian team on FEISTY. FEISTY won the final race, and BLACK SHEEP stumbled again with an OCS that had them last and fought their way back through the fleet to salvage every point they could.
As a result, FEISTY won with 44 pts, followed by JR Maxwell’s SCAMP with 50 pts. Just one point back to take the bronze medal was Sarah Alexander’s MORE COWBELLS with 51 pts. Beasley’s BLACK SHEEP got the short end of that exchange in the last race and well to fourth place with 53 pts. Rounding out the top five was Bengt & Marie’s BLAZE with 59 pts.
J/22 Class
Jeff Hayden and his teammates on the J/22 POLAR EXPRESS battled with their regular rivals on Brad Julien’s YARD SAIL, with Hayden posting a 2-3 to Julien’s 4-1 in the final two races to claim the class title. The delta was only 4 points. Rounding out the podium in third was Jeff Todd’s perennial contender- HOT TODDY.
J/30 Class
Dan Watson’s AVITA was the top J/30 by 11 points, with Watson’s team winning both races on Sunday. They had an unassailable lead over the next two teams on the podium- Valhalla Sailing’s SHAMROCK and Charles Lutz’s POGO, in second and third, respectively.
J/29 Class
Michael Baugh’s J/29 PERSEPHONE, which sailed across the Atlantic Ocean and Delaware Bay to Annapolis from New Jersey to compete with the rejuvenated Chesapeake J/29 fleet, won seven of 10 races to easily win the class. Second went to Glenn Smyth’s SHADOWDFAX with 25 pts, just edging out third-place finisher Tom Lloyd’s ROSALITA with 27 pts.
J/70 Class
Cate Muller-Terhune’s CASTING COUCH convincingly topped the J/70s, counting nearly all podium finishes for a total of 19 pts in 8 races! Taking the silver was Paul Green’s PROGRESS with 25 pts, while Alec Cutler’s HEDGEHOG team from Bermuda won the last two races to take the bronze medal with 30 pts.
J/105 Class
Ray Wulf’s PATRIOT came on strong on the final day with 1-2 finishes to defend their title in the J/105 division. DuPont’s WARBRIDE slipped a bit on the last day with a 3-10 to take home the silver medal, while Bill Zartler’s talented Houston, TX crew on DEJA VOODOO won the last race to jump onto the podium for the bronze medal.
J/24 Class
On the Division 4 race circle featuring J/24s, Pat Fitzgerald’s RUSH HOUR went 1-2 to upset the overnight leaders on Pete Kassel’s SPACEMAN SPIFF. Rounding out the podium for third place was Peter Rich’s BUXTON, just one point back.
ORC Division
The ORC Division enjoyed the breezier conditions and big chop. That favored Jim Sagerholm’s J/35 AUNT JEAN, which ultimately won the race and the ORC title. Kevin Sherwood’s J/99 BAY RETRIEVER took fourth place, while Zack Bayhan’s J/109 PATRIOT VIII was fifth, and Keith Cole’s J/124 LUCKY EIGHTS took sixth place.
For more Helly Hansen Annapolis Regatta sailing information
https://www.sailingworld.com/regatta-series-annapolis/