Cruising Penobscot Bay? Here’s why Castine should be on your itinerary!

Let me start off with a disclaimer—I am biased! I went to college in this quaint coastal town and fell in love with it within a week of arriving from the Midwest. But this year we came to Castine as cruisers and with that in mind, here is why YOU should stop there!

- Mooring/dockage/anchoring. All options are available, whether you pay at the town dock to stay tied up overnight or go to Eaton’s Boatyard, dockage can be found. Eaton’s also has rental moorings. Anchorages with good holding can be found throughout Smith Cove, though that’s a little longer dinghy ride to town. Just want to stay for breakfast at Markel’s or lunch? You can tie up at the town dock for two hours free of charge! It’s even a decent hurricane hole—almost 40 boats were here for the passage of TS Isaias.

- Dinghy Dock. It’s huge! While it can look crowded, we never had a problem “pahkin the cah” here.

- Water/Pump-Out/Trash. Free water is available at both the Town Dock and Acadia Dock, free pump-out is at the Acadia Dock, and trash can be dropped off with the Harbormaster for $2/bag. The Acadia Dock is a “pick-up/drop-off only” dock, so it’s not too hard to get in there for a pump and fill.

- Gas/Diesel. Both are available at Eaton’s Boatyard.

- Food. Provisions are available super close at T&C Market, or further up the hill at the Windmill Hill specialty grocer. Good eats are available at the Captain’s Catch (great fish tacos!), Danny Murphy’s, Markel’s Bakehouse (try one of everything and thank me later), Windmill Hill Grocery, T&C Market deli counter, and Castine Variety. There is currently a pop-up pizza place three nights a week called The Watermark (below Markel’s, call them for info)—it’s amazing! In the time of COVID, everywhere we ate was doing takeout or well-spaced outdoor seating. Bottom line—you won’t go hungry here.

- Shopping. Even now, some shops and art galleries are open. Our family’s favorite is Compass Rose books. They have a great selection of books, international candies (yes, Icelandic chocolate!!!), coffee and snacks, and some seriously nice owners. This place wasn’t here when I was in school, but I sure wish it had been! We also scored a huge bag of books for $5 from a community sale at the local library while we were there!

- Exercise. This is a beautiful, historic town to walk around! From the town waterfront you can easily visit Dyce Head Light, Witherle Woods, and Fort George. Fun fact: the Penobscot Expedition of 1779 was the worst defeat in U.S. Navy history until the attack on Pearl Harbor in 1941! Kayak rentals are available at Castine Kayaks. Landing a dinghy at Indian Bar in Smith Cove puts you in reach of several hiking trails in the Holbrook Island Sanctuary. Smith Cove is well-protected from prevailing summer winds so I was out paddle boarding every morning. A nice long walk will get you to Wadsworth Cove (“the backshore” to locals)  where you can swim in not-so-frigid water in the pond.

So what’s not in Castine? A laundromat and ethanol-free gasoline. That’s the only shortcomings I could find! Whether just swinging in for a pump and fill or lunch, or staying for days, Castine is worth your consideration.

Lehe Paine tied up at the Acadia Dock for a pump-out and water fill. The Town Dock is just in front of us, with dinghy docking on the back side of both docks.

Clockwise from top left: Dyce Head Light, Watermark pizza, Fort George, hiking in Holbrook Sound Sanctuary, dinghy dock, hiking in Witherle Woods to Blockhouse Point.