Sunday, Oct. 16 was the final regatta of the Pen-Bay Fall Series. Boothbay sailors, led by team captain Gabby Boord and including Nate Graves, Ella Beauregard, and Hamilton Barclay, competed in blustery winds of 18-26 knots in Rockland Harbor. The strong winds led to a 1.5 hour delay to the start waiting for the winds to settle down. When the fleet started, the event organizers chose to have just six boats from the A Division compete instead of all 12 boats on the line at once. The B Division rotating in after two races. Eight races were run.

Beauregard and Barclay came out strong with a good start and were the first boat to tack to port favoring the right side of the course were the waves and chop were less. As the lightest and youngest boat sailing, they trailed the leading Rockland team by two boat lengths at the weather mark. The Boothbay boat went high into the passing lane on the first reach of the triangle course and as the Rockland team came up to defend capsized to windward, Barclay steered quickly to avoid a collision as the Rockland mast grazed the Boothbay boat's hull. The race then became a romp for Beauregard and Barclay as they extended their lead at the jibe mark in the heavy breeze and covered to win with the largest margin of the day at 45 seconds.

The second race found the Boothbay boat over early and returning to restart, but ground down three boats to finish third.

Graves and Boord found the first race difficult with boats tacking to cover and unable to get in clear air. They came in fifth but blasted off the start line on the next race and favored the left side of the course but held too long and came in mid fleet in third. Graves and Boord said the first set was exhilarating and a bit scary "as boats were capsizing all over the place."

If the experienced Graves and Boord thought it was scary, it was about to get worse.

The third race for the A Division showed the determination of the young Boothbay sailors. They started successfully at the pin end of the line and were the first to tack-over to port crossing the third place MDI boat, but found they could not cross the Rockland boat. MDI tacked and capsized, then as the Boothbay boat lee bowed the Rockland boat, the Rockland boat tacked and capsized. Believing they had fouled by tacking too close to Rockland, Boothbay began a 720 to exonerate themselves, and capsized. Fully half the boats in the Division had capsized within 6 boat lengths of the line. The MDI boat righted themselves quickly with the Rockland boat quick to follow. They passed all their competitors to finish 1-2. Unfortunately, the Boothbay boat jib sheet remained cleated and after righting it continued to sail although slowly with its crew in the water. After several minutes the exhausted sailors were able to climb back aboard and finish the race rather than take a DSQ. Doing so saved a point. The Boothbay A Boat started their fourth and final race of the day OCS, and returned passing two boats on the way to a fourth place finish. Tired and cold, they passed good information onto Boord and Graves as they headed in to warm up.

Graves and Boord came back in race 3 with their best start of the day charging hard up the left side of the course using their size and strength to keep the #12 boat flat upwind. They rounded the weather mark right behind the MDI boat pushing them hard on the reach but were unable to catch them, finishing second. Their next race found them at the pin at the starting horn going hard, they overstood the port tack layline and rounded the weather mark in third and finishing third as well.

The A Boat ended with 14 points in four races, while the B Boat scored 13 points for an overall of 27 points good enough for third in the regatta. Regatta winner MDI had 15 combined points, which was not good enough to move ahead of Boothbay in the series standings. Rockland Community Sailing Team, the winner of the two previous regattas in the series, held on for second place in the regatta on their home waters. Making for the interesting observation that no team won on their home waters for the series.

Overall Rockland placed first for the series (4 points), Boothbay took second (7 points), and MDI took third (8 points).