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Here follows some notes made from the 2008 TONE cruise to Maine.
Charles Henderson
Aequitas Tartan 34c
There are so many great places to anchor and spend the night in Maine, it is hard to know where to begin. In part, the list varies according to whether you prefer isolated places where you can enjoy nature, including solitude, or whether you like to spend some time ashore, including good restaurants, or other sights. I agree that the TAFT guide is superb. Get a copy of that and notice how many multi star possibilities there are!!!
If it is a once in a lifetime event, and you can visit 15 different places, (don’t forget that getting there is half the fun):
Stop if possible at Provincetown, Mass so that when you depart for Maine your course will take you through Stellwagen Bank and the Northern Right Whale Habitat for some sailing among the whales. Sailing within a couple hundred years of a pod of right whales is awesome. And that is understating it.
You can then head directly for Isles of Shoals or York, unless you follow the alternate strategy of an overnight to the Penobscot region, in which case all of what follows can be done in reverse order. The choice between Isles of Shoals or York is one of those classic Maine decisions based on whether you like the more remote, wilder places or those that give you a sense of what is happening on shore. Both of these spots are not to be missed places, and I can go into details in a follow-up if interested. This applies to what follows as well.
(You might consider stopping at Gloucester and taking the inside route via the Blynman Canal … another story in itself, this will add another day early on to the trip, taking that one away from Maine proper.)
From the York/IslesofShoals stopover, I recommend heading for Biddeford Pool. Actually, you will probably be picking up a mooring in Wood Island Harbor.
Take the Yacht Club launch ashore and enjoy lobster at the seafood market and enjoy a great stroll or walk around Fletcher’s Neck. In the am, don’t miss the bakery and breakfast place about a quarter of a mile down Mile Stretch Road. Here you will find the best blueberry pancakes anywhere, except perhaps Castine, mentioned below. From the tables in front of the bakery, the view of the Pool is terrific.
At this point you are going to make a strategic decision on whether to linger in Casco Bay, taking in for example, the remote Jewell Island, or the last major city, Portland.
(There is also South Freeport and the opportunity for taking in LL Bean and the outlet shopping there, but, again, this is a distraction, and you only have a few days.)
I’d be tempted to shoot for the remote Damariscove Island, a place of legend and a marvelous walking path. OR Boothbay. Or Christmas Cove. Christmas Cove cuts a compromise between Boothbay Harbor with all the shops and restaurants, and Damariscove with the walk, the views and the isolation.
From the Boothbay region you are within striking distance of Penobscot Bay. Monhegan Island should be considered at this point. Another good place to explore on shore with artisans opening their studios for visitors.
If you sail directly from Boothbay to Tenants Harbor, the inside passage around Allen and Burnt Island, past Port Clyde is wonderful. (BTW there are many, many great places to anchor among these islands.)
Just inside Penobscot Bay is Tenants Harbor. You’ll know you are into the heart of Maine as the lobster boats still rule here. I recommend East Wind Inn for dinner with a great view of the harbor, or dining on the dock at the Cod End.
From Tenant’s Harbor, you might want to head for Camden (more civilized) or the more remote Pulpit Harbor on North Haven Island. The sail from Tenants Harbor through Muscle Ridge Channel and beyond is one of the best passages in Maine.
From the Camden region, I would not want to miss Castine. There are several choices for anchoring here, but don’t miss going ashore especially in the morning for a walk and breakfast. There is a bakery with the most wonderful blueberry muffins and a selection of egg sandwiches to die for, which you can eat on the deck, with a distant view of the harbor.
From Castine it is a short sail to Buck Harbor, situated near the entrance to Eggemoggin Reach. “One Morning in Maine,” the Robert McCloskey, classic children’s story was written here. You can sense what inspired him in and around this lovely harbor.
In any case anchoring or picking up a mooring in Buck Harbor sets you up for the passage through Eggemoggin Reach. Depending on the weather and wind, this can be one of the best sailing opportunities. The TONE fleet raced down the entire reach, downwind all the way. A wonderful experience.
At the east end of the reach, I would head directly for the Mt. Desert region. Note, you’ve just left some five star places behind you, but we’ll catch those later.
On Mount Desert Island, there are at least three of those once in a lifetime places: Somes Sound, Southwest Harbor and Northeast Harbor. The cruising guides, including Taft and the Duncan/Ware, “Cruising Guide to the New England Coast” can give you all the particulars. I am tempted, but decided not to include Bar Harbor among the once in a lifetime places, since we are limited to just a few more days, and with three five star places on Mt Desert we are running out of time. In addition, I would not want you to miss: Roque Island. Many consider this the ultimate Maine destination. On our last visit here, shortly after anchoring, at sunset, a horse and rider appeared on the beach.
What a way to top off a Maine cruise. Remember that Rogue Island Harbor is actually part of an archipelago with several different anchoring opportunities.
Assuming you are going to resist temptation and turn back for home at this point. We can now visit some of the places missed on the way down east.
For example, not far from Mt Desert Island is Frenchboro or Lunt Harbor on Long Island. This is another one of those relatively isolated places with a great walk around the perimeter of the harbor, a quaint museum, and a great on the dock lobster and clam chowder place.
At this point, head for Merchant’s Row. There are numerous, wonderful, isolated anchorages here, not far from Stonington, itself a highly recommended place where you can resupply as needed. You are going to have to make some triage decisions here. For example, do you take in Isle au Haut. The later is a great, more isolated anchorage, with a great walk on shore.
Here’s a typical description of this area: a group of 30 or 40 islands lies between Deer Isle and Isle au Haut. Merchants Row, as they are know collectively, is unsurpassed for beauty anywhere in Maine. The islands are all darkly wooded and fringed with white and pink sloping granite shores. Tight passages wind between them, and harbors are everywhere. Even the names of the islands are evocative—Sprout and Potato, Enchanted and Grog, Round, Bare, and Green. Other names remind you that for every island, there is rock—Hells Half Acre and Devil and Wreck Island.
From the Stonington region, continue west toward Vinalhaven through the Fox Island Thoroughfare. North Haven is one of those classic Maine summer places, and I believe Taft describes it well. You are now still located in the heart of Maine sailing territory. And if you take in a few of the places you’ve missed on your route east, you will have spent one of the best sailing vacations of your life. Bottom line, you will try to avoid making this a ONCE in a life time experience.
Footnote RE: fog. We were in Maine as part of the TONE cruise again in August 2010. I would note that during approximately 20 different cruises from Mass or New York waters to Maine and back, including one trip to the Bay of Funday and many, many others to the Mt Desert area, our experience is that in August at least, the fog is much diminished as compared to earlier in the season. Also, with modern GPS, realtime navigation software and radar … not forgetting radar reflectors, fog horn and a good set of ears, you can manage sailing through fog when necessary.
Charles Henderson
Aequitas Tartan 34c
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