Kennebunk River, Maine

New England sailing is easy for those who want to grab a mooring every night; our harbors are plentiful and well-spaced for day trips of 25 to 40 miles. That was our strategy when my partner, John, and I sailed my Catalina 25, Esmeralda, about 700 miles round-trip between Providence, Rhode Island, and Bar Harbor, Maine, last summer—and it worked beautifully under the prevailing summer southwesterlies pushing us north. However, coming back was an issue, as the wind was on the nose and our window of good weather had shut.

When we left Portland, we slogged into the wind for hours, keeping a direct path south as bigger boats taunted us by tacking out to sea and intersecting with our path again and again. They were covering twice as many miles as Esmeralda, but they were sailing rather than motoring at the blistering speed of 5 knots, all my small outboard could manage. My little boat just didn’t handle the chop the way the bigger boats do, so tacking was fruitless. We buckled down, intent on making the Kennebunk River before dark, as John had located a $25-a-night municipal mooring there. We’d hole up for the weekend and wait out the looming bad weather.

Entering a river in a small sailboat can be exciting. Standing waves often form at the mouth during an outgoing tide, and jetties can add an element of anxiety. I’ve trained myself to focus on the channel markers, blocking out everything else. But this time John was distracting me (most likely on purpose) with questions about the late President George Bush, asking, “Is that the Bush house?” and, “Did you know they sent divers to check under Bush’s powerboat before he took it out every time?”

But after the river’s mouth bounced us around a bit, suddenly we were through and it was calm—and tiny! It seemed just a dozen feet wide at first but opened up to a wide, shallow waterway with a well-marked channel. We found the town mooring right in the middle of the channel before Chick’s Marina. Large yachts on the docks made me realize my fear of the narrow channel was misplaced if they’d made it upriver. One bank was busy with hotels and marinas while the other was woodsy and wild. We were happy to be securely on the hook for a couple of nights and close to a new waterfront town to explore.

The town of Kennebunkport buzzed with activity nearby. It was tough to find anywhere to land the dinghy, and we needed ice for the cooler. With some friendly persuasion, a few people let us temporarily tie up to walk into the busy, boutique-y town. At low tide, the boats near us were on their sides, but I only wondered once or twice if Esmeralda’s keel was touching bottom.

The town library, up a street of historic homes, was a nice hangout on a rainy day, and there were plenty of coffee shops and restaurants to kill time waiting for better weather.

Duck Harbor, Isle au Haut

We tucked into Duck Harbor midway during our five-week sojourn. The dock for the daily mail boat from Stonington is right in the middle of the harbor, making Duck Harbor too small for more than three or four anchored boats, but that was fine by us.

Duck Harbor is on the southwest side of Isle au Haut, in Penobscot Bay. The southern half of the island has been part of Acadia National Park since the 1940s; the northern portion is home to about 100 residents. That day we had a gentle southwesterly push us from Tenants Harbor past Saddleback Light squatting on a rocky ledge. We saw one lobster boat that afternoon, and there was one other sailboat anchored in Duck Harbor.

The next morning, we went ashore for a long hike. The National Park Service provides maps of the island’s trails and maintains a few campsites nearby, but we didn’t see other people most of the day. We followed trails up and over the highest point, Duck Harbor Summit, so we could look down upon the little boats in the harbor. Then we meandered through evergreen forests and traced the shoreline where gentle waves went “whoosh” through the cobbles on the beach. We picked wild raspberries and splashed clear cold water from a stream on our necks when the sun burned through the morning fog. At the end of the hike, we were mentally refreshed and ready to sail some more, even perhaps in places where we’d see people again.

Biddeford Pool, Maine

The New England coast is punctuated by numerous coastal towns with harbors, but choosing one that’s the right distance along one’s path isn’t always easy; at the end of a long day, the skipper may not be up to navigating challenges in an unfamiliar place. Had I thought carefully about it, I might not have chosen Biddeford Pool. But once past our first-timer jitters about the entrance, we ultimately embraced the tiny village vibe.

Ledges dot the approach, which made my stomach knot. Worse, one is marked with a vertical post that looks like the mast of a foundering sailboat. Just reviewing the chart and these hazards rattled me when we aimed the bow toward Biddeford and faced the islands that were dark against the setting sun. John patiently described the path we should take between Gooseberry and Wood islands, then how we’d hug the channel close to Stage Island, which is marked by a tall granite tower. From there, we turned south and ran through a narrow gut of water that dumped us in the Pool alongside no more than a dozen other boats.

Once we caught the yacht club mooring and breathed the quiet evening air, we realized what a gem the Pool is. A sturgeon loudly breached the water’s surface again and again as the lights of waterfront homes flickered on. The next day we strolled around the small village where we bought warm blueberry pie a la mode and postcards to send to our grandchildren.

My enjoyment of Biddeford increased when I learned some of the history of the area, including a day during the War of 1812 when a British warship anchored by Wood Island and fired some cannonballs over the village. The Saco River was running too high for any of the residents to escape, so the town’s wealthy store owner sought a bloodless truce at any price. The British reportedly sacked the man’s store and burned his new ship before leaving town.

When we left the Pool, it was with a sense of accomplishment. We’d enjoyed the unique setting and earned a stripe for not turning around when the approach got hairy. Of course, in daylight and with a good night’s sleep, the channel out and around the rocks was a walk in the park. 

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June/July 2024