For half a century, sailors and boat enthusiasts have delighted in one of the Boothbay region’s most anticipated events. This year marks the 50th Boothbay Harbor Yacht Club Regatta, which takes place July 20 and 21 around the harbor and outside of Squirrel Island. It is the oldest regatta in Maine, according to regatta co-chair Bob Scribner.

“Running a regatta for this length of time has required a strong commitment from club members and leaders over the years,” Scribner said. He said the regatta was transformed in 2021 to focus on mostly wooden classic yachts “evocative of a bygone era of sailing,” and the effort has resulted in tremendous growth. 

In 2023, over 60 classic and modern boats competed. Scribner said he expects around 70 yachts for 2024, including the Boothbay Harbor One Design boats involved since the beginning. 

The event also includes the fourth season of the Shipyard Cup Classics Challenge, featuring a slew of classic yachts. The challenge is a nod to the Shipyard Cup superyacht races that were a staple in Boothbay Harbor for over a decade. Between the two competitions, there are 11 racing divisions, including a casual cruising option for first-time racers or those who want to take a scenic cruise around the course.