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kayak kayaking maine paddling Penobscot Bay

Circumnavigating the Cape: A Kayak Trip Around Cape Jellison

One of the great things about Midcoast Maine is that you can find adventure without going far from home.


A friend and I planned to paddle around Sears Island, but the causeway was closed off due to a chemical spill. Plan B? We had no plan B, but the plan that evolved was to launch from the Stockton Springs boat ramp off the Dock Road on Cape Jellison and paddle out to Squaw Point. The sun was warm, the sky was blue, and the breeze was light. We decided to push on along the Cape to Fort Point.

Squaw Point, at the southwest tip of Cape Jellison, offers one of my favorite views of Penobscot Bay. From there, you look past Sears Island to the Camden Hills. You look across the bay to Turtle Head and Islesboro. You look up the bay toward Castine and Fort Point.

The coastline here is rugged, the weathered cliffs broken in only a few places by rocky beaches. I’ve paddled there when the wind was from the south — and the rebounding waves off the cliffs can create confused seas and challenging paddling conditions. On this day, though, a friendly tailwind and light chop out of the southwest pushed us northeast up the coast toward Fort Point.

At Fort Point, after turning to enjoy the fine view out the bay, we passed the high cliffs and the lighthouse and went ashore at the state park — on a sandy spit just north of the lighthouse.

While we ate lunch and relaxed in the sun, the wind picked up considerably. Soon the bay was full of whitecaps — usually an indication of a wind speed of at least 15 knots.

Rather than retrace our route and face that stiff wind over the 3 mile stretch back to Squaw Point, we decided to paddle northwest past the Fort Point docks and through Fort Point Cove to the narrow part of Cape Jellison where we could then walk the mile or so back to our vehicle. The shoreline here provided protection from the wind — and conditions were calm. We easily completed the paddle and walking legs and got back to Belfast just as it was getting dark.

The total distance of the trip was about 7 miles. Unless you are an experienced paddler in a seaworthy boat, avoid paddling the trip when the wind is out of the south. There is no public access and few good places to go ashore in the 3 miles between Squaw Point and Fort Point.