About Cassidy Cup

The mission of the Cassidy Cup is to host a fun, safe and exciting annual woodenboat regatta that connects coastal communities in the Lowcountry and supports educational boat building programs.

The Cassidy Cup is named after Jim Cassidy, a founding board member of the Lowcountry Maritime Society (now Lowcountry Maritime School) . Jim’s dream was to create a wooden boat regatta in the Lowcountry. Unfortunately, in 2015 Jim passed away before his dream came true.

A few months after Jim’s passing, a few good friends got together and decided to race in wooden skiffs from Charleston to Georgetown, for the Georgetown Wooden Boat Show. This race is called the Cassidy Cup!!

The Race
The race is laid out in checkpoints. Race committee will decide on and notify racers of locations and landmarks the entire way of the trip. These locations act as starting lines and finish lines. Each small race is recorded and the racer with the fewest points over the course of two days wins the Cup! Throughout the race, racers are accompanied by safety boats which offer, food, water, sunscreen, safety supplies and a tow whenever necessary.

We keep the fleet together by towing last place boats to
the back of the pack and keep on schedule by towing the entire fleet when necessary.

The regatta begins at sunrise the Thursday before the Georgetown Wooden Boat Show. Participants race out of Charleston Harbor and begin their way up the Inter-Coastal Waterway. Thursday’s destination is McClellanville where participants will make camp, make repairs and adjustments to their boats and get rest for the second day. Day two, participants leave McClellanville at sunrise and head for Georgetown. By the end of day Friday, all racers land in Georgetown.

Race Update
There are talks about changing the race from a 2 day endurance race to a series of races leading up to the Georgetown Wooden Boat Show, including a race during the show. If that’s the case we will have all the dates posted on our calendar as well as how all the points will be tallied for the trophies.

Participant Expectations and preparations
The Cassidy Cup is no ordinary race. Not only is it a challenge of endurance and skill on the water, it is a challenge of skill and ingenuity on land. Participants can race their own wooden boats of all types but the flagship fleet in this regatta is the Bevin’s Skiff, a boat built by LMS students in school programs and summer camps throughout the year. Those who wish to compete in this fleet must find a boat (often available upon request), and convert the boat to sail. This includes building a rudder, dagger board, mast, boom etc. Anything goes in this fleet. The only rules for design are: The rig must be wooden and the hull below the waterline must stay the same.