Celebrating America’s Last Working Sailing Fleet at Maryland’s Iconic Skipjack Races

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Chesapeake Traditions: White Sails Billowing on the Horizon

Each September, sailing enthusiasts gather at the renowned skipjack races to celebrate Maryland’s rich maritime heritage and pay tribute to the watermen who defined a way of life that still endures today. A palpable sense of excitement fills the air, and a chaotic melee ensues as captains aggressively position their vessels at the starting line, preparing to battle the wind and outmaneuver the rest of the fleet. Designed in the 1890s to dredge for oysters, skipjacks are sturdy, wooden workboats—not racing machines. But on race day, these historic vessels glide across the water, their beauty and classic elegance on full display, as they vie for victory.

“The lead up to the race as we’re checking our rigging and preparing to compete is an adrenaline rush for me,” says Shawn Ridgley, the captain of Ida May (built 1906). “Once the starting gun goes off, and we’re out on the water under sail, it’s a familiar feeling. The races are more about strategy than speed, so we focus on tactical maneuvers and harness the wind to gain a competitive edge.”

Not only do the races demonstrate the competitive spirit of the sailing community, they also preserve a tradition that dates back generations. According to Skipjack Heritage, Inc., informal races began during the late 1800s. To test their boats before the start of the oyster season, watermen held “shakedown sails,” which eventually evolved into friendly, yet highly competitive, races. The first official Skipjack Sailing Workboat Race was held in June 1927. 

A nod to watermen, the sailing community continues to celebrate Maryland’s proud skipjack racing tradition at the Deal Island Skipjack Festival, Skipjack Heritage Days at Sandy Point State Park in Annapolis, and the Choptank Heritage Skipjack Race in Cambridge. The races pay tribute to skipjacks and their legacy—shining a light on the importance of preserving these iconic boats for present and future generations. 

“The races are a great way to raise awareness about skipjacks and their history,” says Wade Murphy, III, a fifth-generation waterman and the owner and captain of Rebecca T. Ruark (1886). “Everyone wants to win, so the races are definitely competitive. But they are also friendly. I love being on the water, feeling the wind on the sails, and my blood pumping.”

History of Skipjacks

Skipjacks are shallow-draft, wooden sailing vessels with a single raked mast, two sails, and a V-shaped hull. Built for power, ease of sailing, and affordability, watermen developed skipjacks to harvest shallow oyster beds. Since deeper-draft vessels had exhausted the more accessible beds during the late 19th century, skipjacks were born of necessity. 

According to Maryland Sea Grant, during their heyday (the late 19th and early 20th centuries), these majestic boats dominated the Chesapeake Bay, with historians estimating a fleet of thousands of skipjacks dredging for oysters. However, due to oyster overharvesting, pollution, and disease, the number of skipjacks steadily declined. By the late 20th century, about two dozen were still actively working. Today, they are regarded as a vanishing fleet, and only a few skipjacks continue to dredge for oysters. 

Like all sailing vessels, skipjacks depend on the wind to propel them. But since the wind is highly variable, dredging under sail is not always possible. So, sometimes, skipjacks need a “boost” from a push boat (also known as a yawl boat). These small, motorized boats push the vessels to the oyster beds and back to port and provide power for dredging when there is no wind. 

To prevent overharvesting, the State of Maryland establishes regulations to dictate the use of push boats. Currently, watermen can use push boats two days of the week. During the rest of the week, they must dredge under sail. Dredging season runs from November through March. More than a historic boat, the skipjack is one of the defining cultural symbols of Maryland and the Chesapeake Bay. To honor its legacy, the Maryland General Assembly named it the official state boat in 1985. 

“Dredging for oysters is in my blood, and I love being on the water,” Wade Murphy, III says. “My grandfather did it. My father [Wade Murphy, Jr.] did it, and it goes back even further. I started on a crab boat when I was 13 years old, and I have been on the water ever since. I stopped dredging for oysters for a few years and did carpentry work, but I missed it and got back on the water. I always come back to the water.” 

“Being a waterman has been very important to me,” adds Stoney Whitelock, a fifth-generation waterman and the owner and captain of Han Em Harv (1981). “When I was a kid, the older men would talk about these old boats—which one was fast, pretty, good, bad. That’s all they talked about at Sunday dinner, and I guess some of it rubbed off on me. I fell in love with boats, and I’m still in love with them.”

The Triple Crown

The time-honored tradition of skipjack racing continues this September at three historic races, known collectively as the Triple Crown—showcasing the boats and serving as an enduring reminder of a once-thriving fleet.

In addition to the races at Deal Island and Cambridge, skipjack racing returns to Sandy Point State Park again this year after a highly anticipated race in 2025, which marked the end of a 35-year hiatus. Originally known as Chesapeake Appreciation Days (1965–1990), the event, now called Skipjack Heritage Days, was previously sponsored by the Maryland Watermen’s Association and served as a major fall gathering for the Chesapeake Bay skipjack fleet for decades.

“With fewer than two dozen surviving vessels remaining, Skipjack Heritage Days represents far more than a festival,” says Susan Schneider, manager, Skipjack Heritage Days. “It is the restoration of a cultural gathering place for working watermen, wooden boat preservationists, maritime historians, and the public to celebrate a way of life that shaped the Chesapeake Bay for generations.”

Perhaps one defining feature of skipjack races that distinguishes them from other types of races is the distribution of “show-up” money. Each boat that participates receives funds for maintenance and preservation. Other perks include trophies for the winners and, of course, bragging rights.  

Milestones and Memorable Moments

Whether they are multigenerational watermen who dredge for oysters or skilled skipjack captains and their crews, the sailing community is passionate about the races. The following is a snapshot of a few individuals who made a name for themselves in the world of skipjack racing.   

Stoney Whitelock: A Living Legend

Dredging for oysters has always been a way of life for Whitelock—a proud family tradition that is in his blood. When he retired after a 40-year career as a lineman, he began rebuilding skipjacks to keep them alive for future generations. A “savior of skipjacks,” he resurrected Kathryn (1901), Helen Virginia (1948), Minnie V (1906), and Han Em Harv (1981), previously Anna McGarvey, to their former glory. His son, David, currently owns Kathryn and continues the family tradition of dredging for oysters. In 2013, Whitelock and three other buyers bought Helen Virginia, which he gave to his wife, Katarina Ennerfelt, as a Valentine’s Day gift. Ennerfelt, who was also a co-owner, captained the boat in the Deal Island race in 2014, sailing to victory with an all-female crew and making sailing history.  “The race kind of just happened,” Whitelock says. “Katarina trained the women—some of whom had never sailed before. Since Helen Virginia was still being restored, they practiced on Rebecca T. Ruark and Nathan of Dorchester. And everything just came together that day.” A legendary captain who has attended nearly every skipjack race, Whitelock currently owns Han Em Harv, which he named after his grandchildren, Hannah, Emily, and Harvey. He also serves as the president of the board of directors of Skipjack Heritage, Inc. and the chairman of the Skipjack Heritage Museum. A staunch advocate of skipjack preservation, he played an active role in the revival of skipjack racing at Sandy Point State Park. “The races are a great way to keep these historic boats alive,” Whitelock says. “It was great to see so many people at Sandy Point last year, and I hope we can continue this tradition every year.”

The Murphy Family: A Racing Legacy

When Wade Murphy, Jr. bought Rebecca T. Ruark, the oldest surviving skipjack, in 1984, he established himself as a racing legend. He owned her for nearly 40 years, sailing her as a dredge boat, but, perhaps, the races were where Murphy truly shined. Indeed, since 1988, he sailed Rebecca to victory at the Deal Island race 12 times—more than any other captain in the history of the race. He also won the Cambridge race four times from 2010 to 2014. Rebecca’s story is defined by resilience, and she can perhaps be likened to a phoenix rising from the ashes. She sank, was raised, and has been repaired and rebuilt several times. She even survived being hit by a pickup truck while docked in 2022. After the accident, Murphy decided that it was time to pass the torch to his son, Wade Murphy, III, who bought her and made extensive repairs. “Rebecca T. Ruark is so special,” Wade Murphy, III says. “I raced with my dad for years. But I’ll never know as much as he does. He’d still be racing if he could, but he’s getting older. So, I’ve got big shoes to fill.” In 2025, Rebecca took first place in the Choptank Heritage Skipjack Race. Just as Wade Murphy, III followed in his father’s footsteps and became a waterman, he also hopes to establish a winning streak at the races—just like his dad. “Rebecca is still dredging, still racing, and still winning,” he says. “She’s a good boat, and I hope she lasts the rest of my lifetime—and even longer.”

Shawn Ridgley: A Changing of the Guard

Although he grew up sailing and working with boats, Ridgley didn’t develop a passion for skipjacks until he held positions at Annapolis Sailing School, Living Classrooms Foundation, and the Chesapeake Bay Foundation (CBF). These roles sparked his interest in skipjack racing, and he began competing around 2005, which ultimately led to his association with Ida May. Through his work, Ridgley had met Ida May’s owners, Elbert Jr. and Gordon Gladden, who had inherited the boat from their father, Elbert Gladden, Sr. But at the time, he couldn’t have imagined that he would one day become the captain of Ida May. When Ida May’s captain passed away, the Gladden family—thanks to a good word from Stoney Whitelock—asked Ridgley to become the captain. He took the helm in 2016 and immediately started an impressive winning streak. Ida May won the Deal Island race in 2017, 2018, 2019, 2020, 2022, 2023, and 2025. She also won the race in Cambridge in 2017, 2018, 2019, 2022, and 2023 as well as the race in Sandy Point in 2025. (Ida May didn’t race in 2021 or 2024.) “The skipjack races are a lot of fun, but they are also about camaraderie and fellowship with the sailing community,” says Ridgley, who is the captain of the Maryland Department of Natural Resources (DNR) icebreaker, Eddie Somers. “The sailing community takes care of each other, and their love of skipjacks keeps these historic vessels going for future generations.”

Kate Dumhart: A Steward for the Next Generation

When Dumhart began working at the Calvert Marine Museum (CMM) in 2013, the museum had just acquired Dee of St. Mary’s (1979). And the timing couldn’t have been better. Since Dumhart had experience teaching in an outdoor setting, CMM offered her a unique opportunity. If she learned to sail, she could teach aboard Dee of St. Mary’s. And so, at the age of 26, Dumhart learned how to sail a skipjack and obtained her dream job. Not only did Dumhart gain sailing experience at CMM, but she also became an avid skipjack racer—blending the high-stakes world of racing with her competitive spirit. The first race that she competed in was the 2014 Choptank Heritage Skipjack Race as a crew member on Dee of St. Mary’s. “The year that I first participated in the Cambridge race was the year that Helen Virginia won the Deal Island race,” says Dumhart, also the captain of Schooner SULTANA, a floating classroom that delivers educational programs at the Sultana Education Foundation in Chestertown. “Since the entire crew was female, their victory was inspirational to me. A rare female in a male-driven world is the norm, but Helen Virginia was the exception and the inspiration. It’s great to see women continue to make strides in skipjack racing, which has primarily been a male-dominated sport.” A staunch advocate of Chesapeake Bay heritage and preservation, Dumhart continues to compete regularly in the skipjack races aboard Messenger (1975).

Cyndy Carrington Miller: A Skipjack Enthusiast and Documentarian 

When Miller moved to Maryland’s Eastern Shore from Pennsylvania in 1999, she began doing volunteer work at Richardson Maritime Museum in Cambridge. While working for the museum, she met Captain Frank Newton, one of the captains of Nathan of Dorchester (1994), in April 2022. He invited her to start crew training, and she immediately accepted—even though she knew nothing about boats. “From the moment I saw Nathan of Dorchester and learned about how to sail her, I fell in love,” Miller says. “They couldn’t get me off the boat that summer. I went out for every crew training and signed up for as many trips as possible.” Miller was a crew member on Nathan of Dorchester from 2002 to 2015 and participated regularly in the races in Deal Island and Cambridge. Her experience sparked her interest in skipjacks and inspired her to create The Last Skipjacks Project in 2009. Born from a simple question—“How many skipjacks are left?”—Miller embarked on a journey to track and document the status and condition of every surviving skipjack. She created an online database of her findings, updating it on a regular basis and encouraging website visitors to submit information. “The Last Skipjacks Project is a labor of love,” Miller says. “It represents a vital part of our maritime heritage and highlights the importance of preserving skipjacks to ensure that they are not lost forever.”

Honoring a Vanishing Fleet

The last working sailing fleet, skipjacks are much more than historic vessels that helped shape Maryland’s rich maritime heritage. They are also a symbol of a resilient fleet that may be vanishing but is still very much alive. The celebrated skipjack races pay tribute to these majestic boats. Not only do they offer a thrilling, competitive experience for the captains and their crews, but they also help raise public awareness about the importance of preserving skipjacks for future generations. 

“When spectators watch the fleet race, step aboard a skipjack, meet the captains, or hear the stories of Chesapeake watermen, they begin to understand that these vessels are not merely historic objects,” Schneider says. “They are the surviving expression of an entire maritime culture.” 

Triple Crown of Skipjack Racing

67th Annual Deal Island Skipjack Festival

Sunday, September 6

Live music, Chesapeake Bay educational exhibits, local artisans, and vendors. Skipjacks arrive throughout the day.

Monday, September 7

Blessing of the Fleet – 8 a.m.

Parade of Skipjacks – 9 a.m. Skipjack Race – 9:30 a.m. Best viewing: Deal Island Harbor and along the shoreline of Tangier Sound

Sponsor: Deal Island-Chance

Lions Club. Info: lionsclub-dic.org

2nd Annual Skipjack Heritage Days at Sandy Point State Park

Saturday, September 12

Public sailing aboard historic skipjacks at no cost from 1–5 p.m. from Sandy Point Marina (with Maryland Seafood Festival admission)

Sunday, September 13

Parade of Skipjacks to Sandy Point Lighthouse – 11 a.m. Skipjack Race – 12 noon. Best viewing: East Beach inside Sandy Point State Park

Sponsors: Skipjack Heritage, Inc. in partnership with Maryland Seafood Festival. Info: mdseafoodfestival.com 

30th Annual Choptank Heritage Skipjack Race at Cambridge

Saturday, September 26

Parade of Skipjacks – 10 a.m. Skipjack Race – 11 a.m. Best viewing: Long Wharf Park

Sponsor: Dorchester Skipjack Committee. Info: skipjack-nathan.org

To learn more, visit lastskipjacks.com.