Castine, Maine

Walk the town before anything else. Castine is one of the most walkable villages in Maine, and the architecture tells the story. Federal mansions, Georgian houses, and white-steepled churches line the elm-shaded streets. The town was home to wealthy ship captains in the early 1800s, and their houses still stand. Pick up a walking tour map from the Castine Historical Society at the Abbott School on the Town Common.

Visit Fort George. The earthworks of the British fort built in 1779 sit on a hill above the harbor. This is where the British successfully defended against the Penobscot Expedition, one of the worst American naval defeats before Pearl Harbor. Paul Revere commanded the artillery, and the failure nearly ruined his reputation. The fort is open, free, and has interpretive panels that bring the history alive. The view from the ramparts over the harbor is worth the visit on its own.

Watch the training ship. Maine Maritime Academy’s 500-foot training vessel, the State of Maine, sits in the harbor and dominates the waterfront. MMA students train aboard the ship, and when it is in port, it is an impressive sight. The academy occasionally opens the ship for public tours during summer. Check MMA’s website for dates.

Paddle or sail the harbor. Castine Harbor is one of the most protected and picturesque anchorages on the Maine coast. Kayak rentals are available in summer, and a paddle around the harbor and out past Dice Head Lighthouse gives you Castine from the water, which is really the best perspective.

Walk to Dice Head Lighthouse. An easy coastal path leads from the waterfront to the lighthouse at the harbor entrance. The lighthouse is privately owned, but the trail and views are public. On a clear day, you can see across Penobscot Bay to Islesboro and the Camden Hills.

History Everywhere

Castine’s history is layered in a way that no other Maine town can match. The peninsula was occupied by the French starting in 1613, making it one of the earliest European settlements in New England. The Baron de St. Castin, a French soldier who married into the Penobscot nation, gave the town its name. Over the next two centuries, Castine changed hands between the French, British, Dutch, and Americans multiple times.

The Penobscot Expedition of 1779 was the most dramatic chapter. A massive American fleet sailed into the harbor to dislodge a small British garrison, but poor coordination between the naval and land forces led to catastrophe. The Americans burned their own ships in retreat, losing 43 vessels. Paul Revere was court-martialed for his role, though later cleared. The British held Castine until 1783.

Today, the Wilson Museum on Perkins Street preserves local artifacts and exhibits on the town’s maritime, geological, and Native American history. The Castine Historical Society at the Abbott School has a small but excellent collection of documents and photographs.

Beyond the Village

Witherle Woods, on the south end of the peninsula, is a town-owned preserve with gentle trails through old-growth hemlock forest along the Bagaduce River. It is peaceful, beautiful, and rarely visited. The ancient hemlocks are some of the largest in the area.

Backshore Beach, on the eastern side of the peninsula, is a quiet pebble beach with views across Penobscot Bay. It is popular for walking, beachcombing, and watching the sunset light up Islesboro and the Camden Hills.

From Castine, the Blue Hill Peninsula stretches south and west to Blue Hill, Brooklin, and Deer Isle. A day of exploring the peninsula by car, stopping at studios, harbors, and viewpoints, is one of the finest drives in Downeast Maine.