Atlantic Challenge Red Jacket Youth Sailing Regatta. Atlantic Challenge’s Community Sailing Program will host the 7th annual Rockland Red Jacket Youth Sailing Regatta at their 643 Main Street facility in Rockland. 10:00 a.m. to 5:00 p.m. Sailors from Penobscot Bay sailing programs compete in this fun, one-day regatta promoting sportsmanship, teamwork and sailing skills. Sailors race in single person 8-foot Optis, and two-person 15-foot 420s. Each race runs about 20 minutes, in the vicinity of the Rockland breakwater. The public is welcomed to come watch the races and join a post-race barbecue and awards ceremony. This regatta is named in honor of the Rockland-built clipper ship Red Jacket, launched in 1853 near the current location of Atlantic Challenge. Red Jacket set sailing records that stand to this day.