Penobscot Bay is among the best cruising grounds in the world, sailors agree. The prevailing summer breezes out of the southwest, along with cozy harbors and beautiful water make it all so. Then there are the races — some highly competitive, others, well, it’s all about the boats and having a good time.

2018 racing and regatta schedule

July 26-28, Camden Classics Cup, hosted by Lyman-Morse at Wayfarer Marine, 9 a.m.

The Camden Classics Cup is a two-day regatta that opens the classic sailboat racing season in Maine. The Cup is the anchor event of Camden Classics Week, a week of destination racing to and from Castine, Brooklin, and the outer islands. The Camden Classics Cup is a celebration of both classic yacht racing and boatbuilding. Proceeds from the Camden Classics Cup go to LifeFlight of Maine, with $50 of every registration fee dedicated to Maine’s life-saving service. Last year, the Camden Classics Cup presented LifeFlight with $10,000.

The fleet in dress-ship parades through Camden Harbor for an elegant spectacle and a crowd pleaser.  A big-time fireworks display over Curtis Island Saturday night caps off the regatta. 

Camden Classics Cup is working with Alec Brainerd, president of Artisan Boatworks, in Rockport, to develop a new race class, under 24 feet.

"We hope to draw in Dark Harbor 20s, North Haven Knockabouts (AKA Dark Harbor 17s), and Camden HAJ boats," said Brainerd. "These classic fleets are integral to our summer sailing scene here in Penobscot Bay. It will be great to get them involved in the Camden Classics Cup."

For sailors age 12-17, the Camden Classics Cup Youth Regatta will be held July 27, as they compete on 420s. This one-day race will be held just outside Camden Harbor with 48 racers aboard 24 boats are expected to participate. There is no charge to participate. FMI: camdenclassicscup.com

Castine Classic Yacht Race to Camden, hosted by the Castine Yacht Club, Aug. 2

So begins the annual Wooden Boat Series, which includes the Castine Classic Yacht Race on Thursday, the Camden Classic Yacht Regatta (the feeder race from Camden to Brooklin) on Friday, and the Eggemoggin Reach Regatta on Saturday. The fleet of classic wood racing and cruising boats is impressive and is the largest fleet to race out of Camden Harbor every summer. The ERR fleet often includes more than 90 boats varying in size from 25- to 90-feet with no two designs being the same.

In Castine, on Aug. 1, the Castine Yacht Club will honor some of the world-class sailboat builders from Penobscot and Blue Hill bays: Brooklin Boat Yard, Rockport Marine, Lyman-Morse Boatbuilding, Artisan Boatworks and French & Webb, at an exhibition at the Town Dock and a symposium at Maine Maritime Academy. castineclassic.com

Aug. 11-12, Monhegan Regatta, hosted by the Portland Yacht Club, 9 a.m.

OK, so this is not technically Penobscot Bay, but the competitive race streams by on the waters just to the southwest with gorgeous boats. The focus is on endurance, navigation and strategy, as well as speed. FMI: gmora.org

Aug. 18, Maine Retired Skippers Race, hosted by Maine Maritime Academy, Castine, 9:30 a.m.

The historic race, annually since 1952, is fun and competitive. The retired skippers, age 65 and older, are not to be tangled with on the 12-mile course on East Penobscot Bay. facebook.com/MaineRetiredSkippersRace

 Camden Windjammer Parade

11:30 a.m. to 3 p.m., Camden Windjammer Weekend Parade of Sail to Camden Harbor for Windjammer Weekend. sailmainecoast.com

Sept. 8, Around Islesboro Race, hosted by the Northport Yacht Club, 9 a.m.

Thirty-three years old now, the annual race signals that colder weather looms, and it is a blast for all classes of boats. northportyachtclub.org

Sept. 15-16, Maine Rocks Race, hosted by Rockland Yacht Club, 9 a.m.

This is a long race, 122 nautical miles from Rockland to Matinicus Rock, over to Mt. Desert Rock, then back to Matinicus and Rockland. Phew! It’s endurance and skill, and serves as a qualifier for the Ocean Planet Short-handed Trophy. rocklandyachtclub.org