ROCKLAND, Maine — Captains Doug Lee and Mike McHenry have been handing the Great Schooner Race’s Leeward Class trophy back and forth for years now.

As far as races go, their competition seemed pretty fair: Both 95-foot boats were built in the 1980s. Lee’s Heritage docks in Rockland, where the race started, and McHenry’s Angelique docks in Camden, where the race ended — no home-course advantage.

On Friday morning, the boats left neck and neck from the Breakwater Lighthouse during the 36th annual Maine Windjammer Association’s Great Schooner Race. This year 19 boats competed in four divisions, based on size and build.

For hours the boats stayed close together, passing the Owls Head Lighthouse, going out deep into Penobscot Bay. The yellow Heritage stayed just behind the red-sailed Angelique.

Once the boats started toward Robinson’s Rock off Rockport, Angelique slowed. The wind blew with the boat, making it difficult for the steel-hulled vessel to cut through the calm sea.

“The Heritage caught up. We can get them, but now we’re dead last,” said Angelique passenger Blake Voss of Billerica, Mass.

Voss boards the ketch every year on race week so he and his daughter can see all of the boats.

“This is a close race. For sailboats, this is neck-and-neck. We’re racing that one, that one, that one and that one,” he said, pointing at boats not more than 400 yards from where he was standing, on the boat in the bay. “This will take hours, so it’s anyone’s race. It all depends on the wind. Our boat does better in strong winds.”

With the wind blowing straight from the boats’ sterns to the bows, each of the captains fanned out the sails like wings extending over the water on either side. With 19 boats racing in unison, it looked surreal, like a well-orchestrated fan dance.

This sort of sailing is not Angelique’s strong suit and there was a long stretch where the wind wouldn’t catch the sails just right.

“She goes better windward,” said McHenry, who held the boat’s wood helm. “We are D-L.”

“Dead last,” said a slightly disappointed Marianne Bailey of Glenville, N.Y., who had been sailing on the ketch all week. Bailey has been sailing on the Angelique for 10 years — eight of them during the week of the Great Schooner Race. On Friday, she looked out to sea and saw the Heritage not too far off. “One year the Heritage beat us by half a boat length. This is pretty competitive. But this is not our leg [of the race]. We’ll do better on the next one.”

By the time the boats sailed out deep one last time before heading to the finish line at Camden, it looked like the Heritage would win it. Angelique fell far behind, but the two boats had two different strategies. The Angelique went a bit farther out to sea to catch better wind and Heritage stayed closer to land. By the time the two turned toward land and sailed into Camden Harbor, Angelique took it.

Of course, the three other boats in the Leeward division already had beaten both of them, but McHenry didn’t seem to mind much. The overall winner was the Victory Chimes, a 132-foot ram schooner built in 1900 that docks in Rockland.

“Heritage is the only one that matters,” he said. “We trade that trophy back and forth more than anyone. We’ll give the trophy to someone else this year, but we’ll get it back next year. Every boat has its day.”

After the race, Heritage’s captain sat on deck, sipping a can of Moxie.

“Too much pressure,” said Captain Lee, who was wearing a pair of rainbow suspenders to match his beanie hat. “We ran out of time. But it was the best sailing we’ve had all week. We did come in last, but it’s not a problem. We’re all buddies. Next week I’m sure we will both sail across the bay and I’ll beat him.”