Morning sunshine floods the eastern horizon as Maine’s trademark fog begins to recede. It’s been a push across the Gulf of Maine, but now the delivery miles are astern and a summer season of racing classic yachts is hoving into view faster than Cape Island and the Cuckolds, which collectively guards the southern passage past Squirrel Island and into Boothbay Harbor.
Seagulls cry overhead as harbor seals patrol the shores and play hide-and-seek with the state’s ubiquitous lobster pots. The profile of Kenniston Hill (elevation 285 feet) looms above Boothbay Harbor, and soon the town’s temporary skyline—the rigs of other classic yachts—takes shape. An unspoken excitement settles over the crew as the scent of Maine’s signature conifer forests arrives.
Classic-yacht racing is a long-standing tradition in Maine that has grown in recent years with more regattas and participating yachts. The on-water competition has become more spirited, and the social aspects have been reinvigorated as new faces arrive with tales of restoration projects and spirit-of-tradition builds. The yachts might be old, or drawn to an older aesthetic, and the cruising grounds are timeless, but there’s a gravity to racing classic yachts Down East that draws sailors to a place where time just seems to move a little slower. Sailors secure their docking lines and wander into Bar Harbor in search of coffee, fresh blueberry muffins, and the Boothbay Harbor Yacht Club Regatta and Shipyard Cup Classics Challenge’s registration tent.
While the coming weekend’s challenge will unfurl on the waters off Boothbay, the next few weeks will provide further opportunity for Down East cruising and racing, traveling north to Camden for the Camden Classics Cup, then to Castine for the Castine Classic Yacht Race, and then finally to Brooklin for the Eggemoggin Reach Regatta.
Thoughts of perfect sheerlines ghosting past rocky islands and towering evergreens hold sway as boaters size up the competition, both for their racecourse potential and for their owners’ attention to historical and seamanlike detail. Both matter, greatly. Everyone looks at their own lovingly restored steeds and remembers the long weekends in the shed with sandpaper and varnish in hand, the meetings with naval architects and boatwrights, and the million details that demanded attention.
There are many smiles. It’s taken significant effort to get here, but this will be a summer of classic-yacht racing to remember.
