Cookie Monster crew conquers Annapolis to Newport Race

Annapolis to Newport Race 2024 © Will Keyworth

The Annapolis to Newport Race (A2N) is among the world's most iconic offshore sailing events. Hosted by Annapolis Yacht Club, the 475-nautical mile passage between two historic seaports on the East Coast has tremendous history and tradition. Some of the most renowned racing sailboats in United States history have competed in A2N, which began in 1947.

A2N combines inshore and offshore elements. First, the fleet must negotiate a 120-nautical mile trip down the Chesapeake Bay to Norfolk. Once offshore, navigators must decide whether to sail a rhumb line course or head further offshore. Upon approaching Newport, they must decide if it's favorable to sail inside or outside Block Island. All those factors have made A2N a bucket list item for sailors who enjoy the adventure and sense of accomplishment that comes with blue-water racing.

Stephen Hale was still a novice sailboat racer when he set his sights on completing A2N. Hale and his wife got into the sport in 2015, buying an O'Day 25-footer off Craig's List and learning how to sail on the Potomac River.

Cookie Monster, a Salona 380, is Hale's fourth boat and the platform that gave him the confidence to pursue his dream of offshore racing. "It just seemed like a really cool thing to go out into the ocean and be far away from land," said Hale, who enjoys all the planning and preparation that goes into point-to-point distance racing.

It took Hale a full year to build a solid, consistent crew with most of the sailors carefully recruited from successful boats that participated in the AYC Wednesday Night Races. Meredith Glacken met Hale while both were crewing on J/105s Wednesday nights, and they reconnected at a Fawcett's seminar about ocean racing. Hale ultimately called Glacken in December 2020 and asked her to join the team.

"I sought out Steve because he had garnered a reputation as a competent and competitive racer," Glacken said. "I heard he was assembling a crew to do some ocean racing and wanted to be part of it." The 2021 A2N provided the introduction to ocean racing for Hale and the rest of the Cookie Monster crew. It wound up being a lot more straightforward than the skipper had expected.

"It was pretty much champagne sailing from start to finish. We rounded Chesapeake Light and put up the spinnaker then never took it down." Cookie Monster was the second boat in the ORC 4 class to cross the finish line but corrected to fourth place. There was a tremendous sense of accomplishment coupled with a desire to do even better.

"It was kind of painful to be just off the podium. We went to the awards ceremony and saw people drinking Dark and Stormies out of their trophies," Glacken recalled. "Steve just looked at the whole crew and said: 'We're coming back with a piece of silver next time.' It was really motivating to see Steve so determined to make that commitment."

Hale and his team were exposed to the more harrowing side of offshore racing during the 2022 Newport-to-Bermuda Race as they encountered gale winds and rough seas in the Atlantic Ocean. The Salona 380 was knocked down in a squall and several sails were shredded. "We finished mid-fleet, but by completing that race we came away with more confidence the boat and crew could handle harsh conditions," Hale said. That experience proved crucial in the 2023 A2N.

Cookie Monster was among the Friday starters that had a slow trip down the bay in minimal breeze despite having downwind conditions most of the way. The real test came offshore as the forecasts for brutal conditions proved accurate.

The 39th edition of the biennial A2N will be remembered by the fact half the fleet retired rather than risk damage to the boat or crew in extreme conditions. Many pulled the plug while still in the Chesapeake Bay after carefully reviewing the forecast and confirming the worst — sustained 20 to 30-knot winds and 10-to-12-foot seas.

The Cookie Monster crew put the first reef in the main after crossing the Chesapeake Bay Bridge Tunnel then added another just before rounding Chesapeake Light and heading upwind. That prompted the first discussion about whether it was advisable to turn around. "We really struggled to put in the second reef and were already wet and exhausted," said Hale, who conferred with watch captain Matt Alisch and driver Athena Arnold about the situation. "I wrote in the logbook: Very difficult conditions. Had a long talk with Matt and Athena about whether we should continue.'

Glacken acknowledged it was unnerving seeing numerous boats with capable crew motoring back toward the Chesapeake Bay. "There were a number of boats that poked their head out of the Bay, saw it was just as nasty as forecast, and turned around," Hale said. "No one on the team wanted to bow out. We were leading the fleet to the light and psychologically it's hard to stop racing when you feel you're sailing really well."

Alisch and Arnold expressed confidence the crew and boat could handle the conditions, so Hale elected to keep going and reevaluate at daylight. Members of the Cookie Monster crew refer to those initial 12 hours out in the ocean as the "Night of Doom" since four of the seven sailors were sidelined by seasickness.

Hale and Alisch shared the driving while Glacken handled the trimming as Cookie Monster only managed to log about 12 miles in 12 hours while pounding upwind overnight. Bowman Connor Merryman eventually rallied and came on deck to take the helm for a while. "That first night was really hard and really long. The boat kept launching off waves and slamming back down. It was extremely challenging," Glacken said.

Routing models suggested heading further offshore toward the Gulf Stream for approximately 200 miles before turning left for Newport. Hale was wary of being so far from the coast in such severe conditions because it "would leave us with few options if something broke or someone got hurt. I was committed to staying with the pack," he said.

"What kept us going was that we were in touch with the Navy 44s," Hale said. "We knew the weather wasn't going to last and the wind would eventually back, and we could put up a code sail or an asymmetrical spinnaker and have an advantage over them."

The crew pulled together and squeezed every second of performance out of the boat for the next 48 hours. Merryman and mast man Julius Smith, the other watch captain, performed 12 sail changes in 14 hours while rolling downwind in 20 knots of breeze on approach to Newport. "We were constantly changing gears," Hale said. "Any time we saw an opportunity to get some extra speed, the staysail went up and went down; the spinnaker went up and went down."

Hale believes a crucial moment came in the wee hours of the fourth day at sea when Cookie Monster sailed into a predicted wind hole. "As soon as we hit that lull we immediately tacked, hoisted the Code Zero and footed away. Keeping the boat moving during that period was huge," he said.

Cookie Monster crossed the finish line at Castle Hill Lighthouse Tuesday afternoon and was among the first boats to arrive at the Newport Yachting Center. Glacken said it was "odd getting to the dock and finding no one there."

"It was emotional for the entire team and a tremendous thrill to cross the finish line first in class. It was a remarkable feeling to know that we had really tested ourselves physically and mentally and come together to do something incredible. That whole experience really bonded the team," Glacken said.

Cookie Monster was one of 62 entries in 2023, with 29 crossing the finish line in Newport. The 2025 iteration of the biennial race will take place on Friday, June 6, and Saturday, June 7. Invited classes include ORC Open, ORC Performance-Cruiser, ORC Double-Handed, and PHRF. Starting in the fall, the popular What to Expect Seminars presented by David Walters Yachts will kick off, covering subjects ranging from safety gear to sails and rigging, to medical aid at sea. Online entry will open in June upon the posting of the Notice of Race.