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Small boat Races and Rallies on the Bay!

What We Do:

Raid Chesapeake organizes races and rallies on the Chesapeake Bay.

Raid Chesapeake is an adventure organization that wants to get you to stop daydreaming about small boat expeditions and actually get out on the water!

The Chesapeake Bay is the largest salt water estuary in North America.  With thousands of protected coves and challenging open water, the Chesapeake Bay is the perfect playground for paddlers, rowers, and small boat sailors.

Raid Chesapeake was created by a team of small boat fanatics at Chesapeake Light Craft. We use our vast experience in the world of human- and sail-powered craft to organize races and rallies in the Chesapeake Bay watershed.

Raid Chesapeake wants you to climb aboard your small boat and explore this beautiful estuary, while competing with like-minded smallcraft enthusiasts. At the same time, Raid Chesapeake will work to protect, clean, and honor the Bay while having fun in small boats and challenging paddlers, rowers, and sailors to sharpen their skills.

Upcoming EVENTS

Our mission has two objectives: ​
Broadcast the joy of small boats. Everywhere.

The Chesapeake Bay is home to almost 12,000 miles of the most beautiful estuary coastlines in the world. Whether you've never been on a boat, or you're an old salt, we have a challenge planned for you. 

Do our part to save the Bay!

Every Raid Chesapeake event will benefit some aspect of Chesapeake Bay environmental health. Our events will empower boaters to improve stewardship, celebrate local history, and support local environmental initiatives throughout the bay. 

Our People


Nicky Stimpson - President

Nicky Stimpson found her passion for the water as a young girl rowing a dinghy up and down her grandparents’ lagoon in Forked River, NJ. Years later, she became a 4-year rower & swimmer at Washington College in Chestertown, MD. After falling in love with the sport of rowing, she went on to coach rowing for the next 17-years. The bulk of her career was an 11-year stint as the Women’s Assistant Rowing Coach at the US Naval Academy.
2013 was the first time Nicky stepped onto a Stand-Up Paddle Board, and her enthusiasm for SUP only grew from there. After joining a local weekly race league in the summer of 2016, Nicky has become a regular on the Annapolis SUP race scene. In 2018 Nicky became a certified Instructor with the Professional Stand Up Paddle Association PSUPA and is now an Instructor Trainer with the association.
In 2019 Nicky took on her first long-distance SUP race, SEA Paddle, a 25-mile circumnavigation of Manhattan on a Stand Up Paddle Board. She is currently preparing for Bay Paddle in August 2021 as the first hopeful solo female to paddle the entire length of the Chesapeake Bay on a SUP. 

John Staub - CEO

John's career in the maritime trades began as a child, cruising aboard his grandfather's fishing boat. He spent occasional weekends handing him wrenches and scouring the bay for crabs. Seeds of what would become a life surrounded by boats were planted. 
John stayed close to saltwater in the early years, growing up on a surfboard and sailing around the world compliments of the US Marine Corps. This was followed by a 16-year interval in restaurant management.
In 2013 John moved to Annapolis to finish what his grandfather started: building a career as a boatbuilder and spending more time with his kids. After devoting the first year in Annapolis refurbishing sailboats, John got the long-awaited call to join the Chesapeake Light Craft team. John has been a prolific boatbuilder at CLC and currently serves as CLC’s CEO.

John C Harris - Owner

John C. Harris owns Chesapeake Light Craft, the Annapolis-based purveyor of wooden boat kits and plans. His long tenure at CLC was preceded by a passion for boatbuilding and small craft that stretches back to his earliest childhood. His first (modestly) successful design was launched at age 14. More paddling, rowing, and sailing craft followed quickly, though he paused to get a degree in music - his second passion. After college, he established a career as a boatbuilder, designer, teacher, and writer.   
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