A Case for Trailer Sailing

 

The friends arrived from Maryland, New York, New Jersey, and Pennsylvania to Janes Island State Park in Crisfield, Maryland, on the eastern shore of the Chesapeake. The boats included my B & B Core Sound 20 Mark III, Skeena, two Joel White-designed Marsh Cats, a Handy Cat, a Crawford Melonseed, a Wellsford Navigator, a Rhodes 19, and an O’Day Mariner. The sailors included some retirees, some like me who wished they were retired, and my daughter, who I was happy to have with me for one last adventure before she headed off to law school.  

The May gathering was an annual tradition that brought friends from all over to sail together for a few days. Over the years, the gatherings had been on the Chesapeake in St. Michaels, the Piankatank River, the Sassafras River, and here at Janes Island State Park. Other gatherings had taken place in the Thousand Islands in New York, Lake Champlain, and various places along the coast of Maine. 

We used Janes Island State Park this year as a base camp, and each day began a different adventure, with the highlight a sail to Smith Island to walk around town and procure the famous Smith Island layer cake. Later, rafted together while tucked in the shallows of Smith Island, we cooked a variety of food, talked about life, and a lot of fun was had. Many among this group are musicians, and the songs rang out late. The next morning a fresh breeze had us reaching back to our base at Janes Island. When the wind piped up later in the week, some of us sailed north to the Manokin River and overnighted in the shallows of Wolftrap Creek. Back home in New York, the boat was tucked away to wait for the next adventure while I jumped on life’s treadmill, dreaming of the next adventure.

Read the FULL STORY and see more great photos – click here!

Leave a Reply

Related Posts

Outer Reef 540 Adventure

The Outer Reef 540 Adventure brings serious long-range capability to an owner-operator-friendly package. With a 2,000-mile range, three cabins, a full flybridge, Class A All Oceans rating, and just four feet of draft, the 54-foot expedition yacht is designed to go farther while remaining easy to cruise.

Read More »

It’s Time to Take Back The Water

The used-boat market looks open, but much of the information buyers need most remains behind closed doors. James Evenson examines the influence of Boats Group, restricted sold-price data, rising broker costs, and why he believes the future of boat buying should be built around value, transparency, and trust.

Read More »

One More Weekend: The Annapolis Sailboat Show

The Annapolis Sailboat Show returns Oct. 15-18, 2026, bringing more than 150 sailboats, 550 exhibitors, new boat premieres, seminars, gear, and sailors from around the world to City Dock. Here’s why this four-day tradition is worth building a fall weekend around.

Read More »

Categories

Categories

Current Magazine

Recent Posts