THROUGH THE LENS: Chesapeake Bay Magazine

Through The Lens: Photography Students Meet The Lesser-Know Chesapeake

Originally published in Chesapeake Bay Magazine on November 1st, 2024 by by James Ronanye


One of Jay Fleming's workshop group takes photographs of Prospector hauling eel pots at the mouth of the South River. Photo: James Ronayne

Every year, millions of people enjoy seafood from the Chesapeake Bay, where the blue crab, striped bass, and oyster fisheries collectively contribute over $100 million to the local economy. But how many people know the faces behind their seafood? Photographer Jay Fleming has helped educate these seafood consumers through his immersive on-the-water photography workshops. He brings his pupils to some of the most remote Bay communities for rare access to the watermen’s way of life.

Fleming steers his 18-foot Privateer in front of the workboat Pilot’s Bride. Photo by James Ronayne

Fleming has been taking pictures since he was 13 years old, when he discovered one of his father’s old 35mm film cameras. When he grew up, Fleming spent the first part of his career working for the state of Maryland in seafood marketing. His job was to help bridge the gap between harvesters and consumers.

After leaving his state job in 2015 to work as a freelance photographer, Fleming has been “working the water” with his camera, revealing a behind-the-scenes look at the people, products, and processes of the seafood industry. “Being able to connect with the watermen community has been one of the most rewarding parts of my job,” says Fleming. To share this experience with like-minded photographers, Fleming started offering photography workshops on Smith Island. The isolated island was an ideal location for photographers with abundant wildlife and a fleet of working watermen. His workshops have since evolved to cover multiple locations. He now has his U.S. Coast Guard captain’s license and a boat custom fitted to navigate the shallow waters of the Eastern Shore. 

Photographing the 2023 Deal Island Skipjack Races. Photo by James Ronayne

2024 marked a record year for Fleming’s workshops. This season, he hosted more than 150 photographers and introduced them to the working side of the Chesapeake that few get to experience. With workshops out of Cove Point Lighthouse, Hoopers Island, Smith Island, Tangier Island, Annapolis, and Deal Island, Fleming was able to find his students different subjects to photograph. “Each location offers a unique glimpse into Chesapeake culture, landscapes, and different fisheries. These workshops provide exclusive access to watermen and a behind the scenes look at the seafood we all know,” he says.

A workshop student makes the famous Smith Island cake with baker Donna Evans.Photo by Jay Fleming

From finding the bay’s most remote bird nesting sites to photographing the making of a Smith Island cake, photographer Kim Kelly has covered it with Fleming. She has attended one of Fleming’s workshops in every location. “To best capture the waterman’s way of life, you have to experience it firsthand,” she says.

Photographer Kim Kelly has taken workshops in all of Fleming’s locations. Photo by Jay Fleming

Fleming’s personal connections with the working men and women of the Chesapeake give his students the access needed to get the shot. His trips allow budding photographers to expand their skills and portfolio, but the real value of the “Jay Fleming Experience” is the social and environmental education he provides. His students learn firsthand about the environmental challenges posed to the Chesapeake and how locals have adapted to deal with them. “Jay has opened my eyes to a changing way of life through his workshops. I have a newfound appreciation for the seafood industry and the hard work that goes into bringing it to our tables from being on the water with Jay,” Kelly says. 

Fleming’s workshops aren’t just beneficial to photographers; they also positively impact the watermen and the seafood industry. Eddie Somers, a Smith Islander and head of the island’s advocacy group, Smith Island United explains, “Jay’s trips have brought hundreds of photographers to Smith Island. His trips showcase island life and our local seafood economy in a positive light. The experiences that he provides his students build an appreciation for our community. A handful of his attendees have even come back out on their own. This new form of photo-eco-tourism will be an important part of the island’s future economy.”

Fleming and longtime waterman Bobby Washington pose with photos of Washington dredging for oysters. Photo by James Ronayne

On any given morning the waterman greet Fleming with a smile. The men and women of Smith Island understand and appreciate Fleming’s motivation to educate his fellow photographers. Many of them are proudly displaying his prints in their homes. The islanders affectionately refer to Fleming as “Flanigan” and they can recognize his gray Privateer boat coming from miles away.

Through his workshops, Jay Fleming shines a light on the Chesapeake seafood industry, generating new interest and attention from a positive lens. His education not only in photography but also in environmental issues is a rare combination. While Jay Fleming may not work the water in a traditional sense, his work documenting his home waters plays a role in preserving the Chesapeake’s legacy and introducing new generations to its rich heritage.

Fleming follows Annapolis trot liner Jack Torney with a group of high school photographers. Photo by James Ronayne

Competitive Boat Docking on the Chesapeake Bay

Competitive boat docking is a tradition that goes back 50+ years on the Chesapeake Bay. The first contest was held in 1971 at Crisfield's hard crab derby - a weekend celebration of everything crab. Dwight Marshall from Smith Island was the first to take the title and now his son and grandson are competing in the Chesapeake Cowboys circuit to carry on the family legacy.

I spent the a Saturday this September at the Brew River competition in Salisbury, Maryland for Thrillist documenting the rivalry between the competitors and the energy of the workboats in motion.

Check out the the link below for more photographs from the event and the story by writer Katie Riley:

Galápagos Islands Photography Workshop - January 2024

In early January I co-led my first international photography workshop in the Galápagos Islands with Emily Carter and 14 photographers from the Chesapeake region. The trip was organized by Holbrook Travel - a family owned and operated travel agency that has been working working in Latin America since the 1970’s. Our group cruised around the western route of the Galápagos for eight days under the expert guidance of national park guide Edgar Vargas. We had incredible encounters with a diverse array of wildlife on land and in the water. Enjoy the Photographs of the group and the crew from the Tip Top II.

Emily and I are in the process of scheduling the 2025 trip to the Galápagos Islands with Holbrook Travel - stay tuned to my blog and social media for more information!

The group at Isla Seymour Norte on day 2 of the workshop.

We cruised the islands onboard the catamaran Top Tip II. The 104 foot long catamaran with a 40 foot beam provided our group of 16 plenty of space to spread out. The boat has 10 cabins, two dining areas, a bar and a upper sun deck. The crew and national park guide, some of them pictured below, did an incredible job making the experience memorable and the accommodations more than comfortable.

Emily Carter leading the group on a hike to the highest point on Bartalomé Island.

With the Top Top II as our mothership, the captain and crew used two zodiacs for our land and water based excursions on the different islands in the Galápagos.

Workshop participant Tracey Richardson from St. Michaels, Maryland photographing sunset on day six of the cruise through the islands.


Workshop participant Bill Mish from Annapolis, Maryland set the bar for underwater photography on the trip. Bill has been free diving and shooting underwater for more than three decades. The group had incredible opportunities for underwater photography during more than ten snorkeling excursions.


Group selfie on the ride up to the highlands on Floreana island.

Coming back to the Tip Top II at dusk after a shoot on Isabela Island.


The group at Hacienda la Compañia in Cayambe, Ecuador. Before heading to the Galápagos, we had a day in the Quito area to tour a rose farm and have a traditional Ecuadorian lunch in this beautiful colonial estate.