The 2023 edition of the Annapolis-to-Newport Race was special for Annapolis Yacht Club member Ken Comerford, a veteran offshore sailor with thousands of blue water miles under his belt. Comerford skippered his J/121 Dark Storm to victory in ORC 2, which was one of the largest classes with 16 boats. Dark Storm was the second Saturday starter to cross the finish line at Castle Hill Lighthouse, posting an impressive elapsed time of 3 days, 3 hours, 27 minutes and 41 seconds. That produced a commanding class victory on corrected time as Dark Storm beat Sonrisa, an XP 44 skippered by Jeffrey McCarron, by almost an hour.

But just to finish the 475-nautical mile passage was a tremendous accomplishment. The 39th edition of the biennial Annapolis-to-Newport Race will be remembered for the 31 of 60 starters retired rather than risk damage to their boat or crew. Comerford was quite satisfied with his crew, who displayed outstanding skill and seamanship as well as great toughness and determination during the extreme conditions offshore. Most boats pulled the plug while still in the Chesapeake Bay after carefully reviewing the forecast and confirming the fleet would be welcomed into the Atlantic Ocean by 20- to 30-knot winds and 10- to 12-foot seas. Simply surviving the brutal conditions mother nature dished out during the initial 24 hours in the ocean was a challenge. Comerford said the 12-mile stretch from the mouth of the Chesapeake Bay to Chesapeake Light was particularly brutal.

“Getting out of the bay was really tough and then we had a bit of a hate mission from the tunnel to the light,” Comerford commented after arriving safely at the Newport Yachting Center. “We had a lot of water on the boat and everyone was pumping.”

Dark Storm had six crew members that were capable helmsmen and Comerford thought that was critical during a nearly 30-hour beat into stiff winds and heavy seas. The J/121 was
double-reefed and flying the No. 4 genoa as it faced a maximum wind velocity of 33 knots.“No one drove for more than an hour or so. Whenever you couldn’t go anymore, you tapped out and we switched someone else onto the wheel,” Comerford said.

While handling the extreme conditions was critical, Comerford believes the race was actually won a day later when the entire fleet became becalmed. That is when the Dark Storm brain trust had to make some important decisions about where to go.

“We had some boats out to the west that were in front and some to the east. We were kind of in the middle and really nervous about where we should be,” he said. “We kept having these major discussions: Should we go west or go east? I finally told everybody that we just needed to keep making the boat go forward the best we can. We made the middle work and got out in front of everyone, then got a big shift and were able to sail into Newport on a long reaching leg.”

Comerford was in for a pleasant surprise during the prize-giving ceremony held at Waites Wharf. He was presented with the James Allsopp Seafarer Trophy, which is awarded for best combined performance in the Annapolis-to-Newport Race and the Newport-to-Bermuda Race. Dark Storm had placed third in Class 18 for the 2022 Newport-to-Bermuda Race.

More than a year later, Comerford got choked up when asked about earning the special award, which was renamed in honor of Allsopp prior to the 2017 edition of A2N. Allsopp, who operated the North Sails loft in Annapolis for nearly three decades, was an early mentor when Comerford came to Annapolis and got involved with sailboat racing.

“Jimmy was someone who meant an awful lot to me, so it was awesome to win the award named in his honor,” Comerford said. “Jim always did a tremendous job promoting the sport, and I was among many young sailors he took under his wing.”

Comerford was working as a salesman for Salomon Skis when he moved to Annapolis in 1988. He quickly developed a passion for sailing and spent considerable time on the water, crewing for skippers such as Glenn Robbins, Steve Hiltabidle and Pen Alexander. He competed aboard big boats in the Annapolis Yacht Club Wednesday Night Series and learned how to sail a Laser during the Tuesday Evening Series for One-Design out of Severn Sailing Association.

“I sailed a ton my first few years in Annapolis and realized I really loved the lifestyle and the people,” said Comerford, who became a member of the Sailing Club of the Chesapeake in 1992 and did considerable cruising.

Comerford was introduced to offshore sailing by doing boat deliveries with Dave Dunigan, who was another important mentor. “Dave and I sailed a lot of ocean miles together and he taught me a lot about boat preparation, operation and maintenance,” he said. Comerford bought a Cal 40 named Phantom in 1996, thoroughly renovating the classic sailboat and preparing it for the 2000 Newport-to-Bermuda Race. His first Annapolis-to-Newport Race as an owner came aboard a Beneteau 40.7 named Moon Racer. He subsequently campaigned a Beneteau 36.7 (Jubilee), Beneteau 10R (Moon Racer), J/120 and J/111 (both Moneypenny) before acquiring Dark Storm.

One of the more memorable passages for Comerford was crewing aboard Y2K, a Swan 68 owned by Charles Engh, overall winner of the 2003 Annapolis-to-Newport. In total, Comerford has completed the Annapolis-to-Newport Race six times — four as crew and two as skipper of his own boat.

“Annapolis-to-Newport is an incredible race because it gives you every aspect of sailing. Getting out of the Chesapeake Bay is a big part of that race and then there are some critical decisions to make offshore,” Comerford said. “I think Annapolis-to-Newport is ideal for introducing sailors to coastal racing. You get all the thrill of being out in the open ocean, but you are also relatively safe in terms of being within distance of the Coast Guard or getting back to a port.”

A2N connects two of the oldest, most historic seaports on the East Coast and Comerford enjoys welcoming out-of-town competitors to Annapolis before the start then spending quality time in Newport following the finish.

“We love Newport almost as much as we love Annapolis. We always go to the Black Pearl for clam chowder and to the Candy Store for a crew dinner,” he said. “I love walking around the Newport Shipyard and looking at all the different boats. We ride bikes around the island and go to the beach. It’s a great city to explore.”

Comerford is well into the planning and preparation for the 40th Annapolis-to-Newport Race and is looking forward to defending its class championship. Ocean racing has gotten into the longtime Annapolis Yacht Club member’s blood.

“There’s just something magical about ocean racing. It’s somewhat of an escape that allows you to disconnect from the world. It’s all about getting out on the water with your boat and your crew and having a good time,” Comerford said.

Comerford cited regular and reliable crew as a key to success in offshore racing and offered some other advice for skippers considering doing the Annapolis-to-Newport Race.

“Once you get more offshore racing under your belt you recognize all of the important factors that go into a successful passage. It’s important to have proper boat preparation, a good navigator and a solid strategy. I think it’s critical to have a crew that is competent and gets along well,” he said. “It’s kind of the whole package you get when you go distance racing. If you have all the key building blocks in place you are going to be more successful.”