Walking Through History in Mid-Coastal Castine, Maine
Castine is a coastal town in Maine that is home to the Maine Maritime Academy and has significant Revolutionary War history. I didn’t know any of this prior to stopping here during a coastal sail through Penobscot Bay on the Windjammer Angelique. In fact, Castine is one of the oldest continuously occupied communities in America. Since the early 1600s, it has been the site of numerous trading posts, forts, missions, and settlements of France, Holland, England, and colonial America.




Above photos: Harbor
Castine can be reached by car. It is 138 miles north of Portland or just 53 miles north of Camden. Alternatively, boats can anchor in Castine Harbor and take a dinghy over to the wharf.
We had just a few hours to explore this little town and were able to cover quite a bit of ground in that short amount of time. As soon as I got up to the main road from the harbor, I grabbed a walking tour brochure and set off to see the historical homes and town buildings. Amongst the highlights of the charming seaside town are:
- Main Street
- Pentagöet Inn
- Public Gardens
- Court Street
- Adams School
- Castine Historical Society Buildings
- Castine Cemetery
- Perkins Street



Above photos: Restaurants and shops (left and center); the historic Pentagöet Inn (right)
Main Street has a few shops and cafes, as well as some notable historic buildings. One of the most prominent of these is the Pentagöet Inn, a bright yellow Queen Ann Victorian built in 1894. Besides their charming lodgings, they also have an acclaimed restaurant.
Directly across the street, there is a beautiful public garden between the Castine Inn and the Old Post Office. Whatever the folks here have to endure during the winter months, mother nature compensates for during the summer with lush gardens and the biggest peonies I have ever seen.
The steeple from the Trinitarian Congrational Parish can be seen rising above the trees along Main Street. The church was built in 1829, and the spire added in 1867.






Above photos: Public garden; Trinitarian Congrational Parish (bottom center)
We took a right onto Court Street, where there are several other buildings maintained by the Castine Historical Society. The Abbott School, once a primary school, is the current location of the Castine Historical Society. Inside are two permanent exhibits including the 1779 Penobscot Expedition and the a community quilt commemorating Castine’s bicentennial. In close proximity, the Unitarian Universalist Congregation is the oldest meeting house in eastern Maine.


Above photos: Abbott School (left); Unitarian Universalist Congregation (right)
Towards the end of Court Street, the Castine Cemetery is a beautiful place to visit to admire the intricate carvings and weathered patinas on sea captains’ headstones, reminders of Castine’s seafaring past. The cemetery was larger than expected, so I spent some time here enjoying the peace and surroundings in this wonderful resting place.




Above photos: Castine Cemetery
The last bit of remaining time in Castine, I took a walk down Perkins Street. The homes along this street look out to Castine Harbor and are flanked by elm trees that have probably been here longer than the British. Some are on the National Register of Historic Homes. Of course, most of these homes have been through some renovations over the years, but from the outside are impressive examples of Colonial architecture.
I especially enjoyed the historical markers along Perkins Street that offered some good storytelling. The Castine Historical Society noted that not all of these are totally accurate. But, that’s okay. The point is, there is a lot that transpired here over the years.






Above photos: Perkins Street in Castine, Maine
If you have more time in Castine, consider following Perkins Street to the Dyce Head Lighthouse, built in 1828 and still active. We got a peak of it from the water:). The lighthouse is located on private property, but open to visitors during the day.

Above photo: Dyce Head Lighthouse
I didn’t have time to explore the Maine Maritime Academy. However, the college is probably the biggest draw to the town. It has an undergraduate enrollment just under 1,000 students. For a small town like Castine, that is a sizable chunk of its population. Likewise, its 500-foot naval research ship, the TS State of Maine, it a sizable presence in its harbor.



Above photos: TS State of Maine (left and center); Maine Maritime Academy founders rock (right)
I left completely enamored by this special place. Obviously, I’m not the first one as so many others have recognized its beauty and prime location. No surprise that it was fought over and nicknamed the “battle line of four nations.” What a true gem of a New England town!
Read about our full week of coastal sailing aboard the Windjammer Angelique.
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