Sept. 15, 2026 Castine to Southeast Harbor anchorage

Sept. 15-16, 2026 Castine to Southeast Harbor Anchorage 32 miles and 3.5 hours

Good night on the mooring ball as the winds continued to subside. Not sure who's ball it was but we thank you! Nice blue skies and light winds to start the day. Dropped the line and headed over to the town dock at Castine. Make our way behind State of Maine from the Maritime Academy and find the town dock empty except for one small boat, so plenty of room for us. Got there a little after 10. With a 2-hour docking limit during the day, we needed to get gone by 12:30. First impression is it's a very small commercial area on the waterfront. Just a couple of stores and restaurants. Stopped at the visitor's center and picked up a very nice walking tour map. For such a small town they also have a great app to use while walking the town with audio available to listen at each stop. Wish more towns would make this type information available for visitors. Enjoyed our time walking the tree lined streets with many older houses being kept in outstanding condition. Very New England feeling with white painted houses rather than the more typical coastal style of naturally weathered cedar shakes. Good presentation at the historical society about the Penobscot Expedition. During the Revolutionary War the British captured the town and had started building an earthen fort. Castine was still part of Massachusetts at the time, and a large flotilla of ships, transports and Patriot men were sent to oust the British. Terrible communication between the Patriot Commanders resulted in an embarrassing defeat. Considered the worst naval defeat in US history until Pearl Harbor. Still used as a case study by the military today.

Here's a link to the app if you're interested in a virtual tour.

https://apps.apple.com/us/app/castine-history-highlights/id1438564894.

Pentagoet Inn and Restaurant built 1894.
Served as the original home of the Maine Maritime Academy back in 1941

The 1814 customs house. Castine was one of 10 designated
official ports of entry in Maine - hence much of the towns early wealth. Currently
houses the second oldest Post Office continuously operating in the same building.

Trinitarian Congregational Church circa 1829 has been expanded
numerous times since it's founding

Couple of nice houses on Main Street

Preservation work in progress

The Town Hall is housed in an historic building donated by Charles Emerson

Halloween decor starting to come out means it's about time for us to head south

The Adams School circa 1852 still serves K-8 students.

The town square is up the hill a few blocks off the waterfront. Only one monument on the square. Honors local citizens who died during the "War for the Preservation of the Union"

Historical Society housed in the 1859 Abbot School building on the left.
Used as a Teachers School after the civil war and then as a High School until 1961

Back to the boat after our rushed tour. Definitely could have spent a few more hours there but we've got about a 3-hour cruise to our next anchorage and need to get going. Slight breeze but sunshine so not too chilly despite temperatures remaining in the 60's. Work our way down the West Penobscot River passing numerous granite islands, sailboats, lobster boats and of course lighthouses.

Nice day out on the water - light breeze, sunshine, calm waters

Windjammer taking a group for a cruise

1838 Eagle Island Lighthouse. We thought the other building was a
teepee when we were first approaching. Actually, a fog bell tower.

Working our way through some more scenic area

Crazy to think of the effort required to wear these granite areas smooth

1857 Deer Isle Thorofare lighthouse. Marks the western entrance to Stonington

You could almost enjoy the scenery, if not for the constant
focus required to avoid the lobster traps

Turn to port puts us on the Deer Isle Thorofare. Town of Stonington is in the center of this stretch. Stonington is ground zero for the largest collection of lobster boats in the area and the surrounding waters testify to it. Cram full of trap buoys. Some great anchorages close nestled in a congregation of islands but the lobster boats passing around them starting at 4:30AM makes them a bit uncomfortable. We pass through the thorofare and eventually turn north heading towards our anchorage up inside of Deer Isle.

Entering the thorofare

Saw several boats stopping at this float. Not sure if dropping
off their lobsters or picking up fresh bait.

Fishermen's homes cling to the shoreside while their boats bob on moorings

No real harbor here - just several commercial wharfs

By late afternoon every mooring will be occupied by lobster boats.

Here comes another lobster boat charging into town with his catch

Southeast Harbor is a nice, protected area. Not a working harbor - more a harbor of refuge. Several good places to drop the hook. Natural surroundings with rocks and trees for protection from winds in just about any direction. Couple of reviews mentioned good seal watching area. We've seen a couple of heads pop up but that's been about the extent of it for us. Once again, we're the only ones here. I'm beginning to think most cruising boaters may already be headed south.