The Ultimate Maine Cruising, Racing, Cruising, Racing-Racing, Cruising Guide

Maine as a racing and cruising destination? Who ever heard of such a thing. But at least for the summer 2018, it seems to be true. We’ve been taking a deep dive into the coming classic yacht-racing schedule, and wouldn’t you know it — with no particular organizing body involved — little old Mid-Coast Maine has become a must-do race and cruise stopover for late July and early August.

If you have ever dreamed of making the trip Down East, here’s the perfect cruising, racing, cruising, racing-racing, cruising guide to Maine.

The Camden Classics CupJuly 26 – 28. Maine is cruising central at the end of July. And all the world knows it: Moorings, private anchorages and good tables at good restaurants come at a serious premium, of they can be had at all. The Camden Classics Cup is set up to solve all those logistics headaches. For one price of entry, all racers get the greatest landfall on the American Eastern Seaboard: The run up Penobscot Bay into the Camden Hills. Plan it for a dawn, when the light is best. And when you get into Camden Harbor, you can check in at Lyman Morse Boatbuilding, organizers of  the regatta. And then head off to Bagel Cafe for breakfast. So far your raft-up neighbors will include some lovely SoT classics, like Vortex, Dreadnought and Lynnette. The Camden Classics Cup is the perfect gateway to Maine and the marine narratives we hold so dear.

The Castine Classic Yacht Race to Brooklin, Aug 1-3  After two days of great racing, followed by three days of cruising in and around Penobscot bay,  (if you need secret spots to cozy up into in Vinalhaven, The Fox Islands Thorofare or Blue Hill, give us a holler) the next racing stop is Castine, Maine and the Castine Yachts Club’s Yacht Race to Camden. This once feeder race for other events has come into its own recently. Organizer have brought in seriously interesting speakers. On August 1st there will be a fascinating symposium on Maine yacht design and construction, featuring many of the great local yards … and us. That will be followed by some racing including the Camden Classic Yacht Race to Brooklin, that sends the fleet through the heart of Penobscot Bay. And just to show you how old school this race is, rules require the towing of a legit dinghy, which makes port and starboard crosses all the more entertaining. (Yup, that dingy back there has all the rights of any boat on the course, big and small)

All of which tees racers up for the climax of the series the …

Eggemoggin Reach Regatta: Aug 4

We’re biased, but the the granddaddy of all races with great stories is the Eggemoggin Reach Regatta, which runs this year on August 4. This event is not the oldest, but it is one of the best! Founded in 1985 by our friends Steve White and Frank Hull of Blue Hill, Maine, the race regularly draws over a hundred of the finest classic and Spirit-of-Tradition boats from around the world. There’s so much to love in this race: Gorgeous Maine scenery, carefree mid-coast atmosphere that eliminates the stuffy scene that suffocates regattas south of Cape Cod. In fact, we feel there’s no better race to finish last in. You just got to spend the most time out there in these marvelous waters. Just check out the course map, pictured to the right.

Then you can get to imagine it: All provisioned and practiced and within an easy sail to Swans Island, Blue Hill Bay, and Mt. Desert and then on and on, until the time and tide overwhelm you.

You quite literally may never go home again. We never did.