Southport Watersports Events - 2026 Schedule

Labor Day weekend on Bald Head Island is truly a celebration, and the annual Labor Day Cookout offers a lot more besides a chance to feast on burgers and beachy fare. With corresponding activities and events held all along the island, and plenty of unique attractions to discover along the way, the annual celebration is a prime opportunity to uncover everything this popular North Carolina vacation destination has to offer.

Labor Day weekend on Bald Head Island is truly a celebration, and the annual Labor Day Cookout offers a lot more besides a chance to feast on burgers and beachy fare. With corresponding activities and events held all along the island, and plenty of unique attractions to discover along the way, the annual celebration is a prime opportunity to uncover everything this popular North Carolina vacation destination has to offer.

The Carolina Beach Dragon Boat Regatta is an annual community festival and paddling competition that brings together teams, spectators, businesses, and local organizations for a weekend of fun, teamwork, and friendly competition along the Carolina Beach waterfront. Organized by The Island Men, a nonprofit volunteer organization serving the Pleasure Island area, the event features colorful dragon boat races in which teams of paddlers compete in traditional 45-foot-long dragon boats while a drummer keeps the crew synchronized. The regatta has grown into one of the region’s signature waterfront events, attracting participants from across southeastern North Carolina and beyond.  

The Outrigger East Coast Championship is a premier paddling competition that draws elite outrigger canoe teams, paddlers, and water sports enthusiasts from across the United States to Wrightsville Beach for a weekend of endurance racing and coastal adventure. Hosted by the Wrightsville Beach Outrigger Canoe Club, the annual championship is recognized as one of the East Coast’s most challenging and respected outrigger canoe events, attracting both seasoned competitors and newcomers to the sport. The competition showcases the skill, teamwork, and athleticism required in traditional outrigger canoe racing while highlighting the unique waterways and ocean conditions of southeastern North Carolina.

The annual U.S. Sailing Youth Championship is coming close to home for Cape Fear mariners, and participants and spectators alike will find plenty of reasons to cheer at this annual event. Held at the Carolina Yacht Club at Wrightsville Beach, this annual competition is an exciting sporting event that features top young sailors from around the country in a challenging race that circles the beautiful Cape Fear coastline.

The annual U.S. Sailing Youth Championship is coming close to home for Cape Fear mariners, and participants and spectators alike will find plenty of reasons to cheer at this annual event. Held at the Carolina Yacht Club at Wrightsville Beach, this annual competition is an exciting sporting event that features top young sailors from around the country in a challenging race that circles the beautiful Cape Fear coastline.

Celebrate the season in true coastal style with this annual event that has become a tradition for Southport locals and frequent visitors alike. The Southport Christmas Flotilla features a beautiful array of decorated vessels of all varieties that are decked out for the holidays, and which pay homage to the maritime spirit that is inherent in this small coastal town.

Pleasure Island is inherently known for celebrating life on the water, and at this holiday event, spectators and participants alike will enjoy a glowing show in one of the prettiest corners of the waterfront Cape Fear region. The Island of Lights Christmas Flotilla is an annual tradition that rings in the holidays with plenty of dazzling style, and which is sure to charm and delight anyone with a front-row seat along the Intracoastal Waterway.

Athletes of all abilities will want to join in this event which provides a chilly way to celebrate the winter season while supporting a very worthy and local cause. The annual Polar Plunge, 5K Run-N-Plunge, or one-mile fun walk is a great way to experience the stunning Kure Beach shoreline in the off-season months while having a chilly but fun time embracing an inner superhero.