No one strays into Castine. It’s not on the way to anyplace, and it contains only a handful of shops. But in this almost-too-perfect New England town, you can stroll shaded sidewalks past classic Federal houses as a historic church bell tolls in the distance. On a fine fall day in Maine, everything here dazzles, from the white houses to the indigo bay sliced with white sails.
I thought I knew Castine. I can point out the houses where novelist Mary McCarthy and poet Robert Lowell once lived, as well as the home of contemporary poet Philip Booth. I’ve bounced over local roads from my nearby summer place to have dinner with Castine friends. But this visit will be different. Determined to savor the town’s layered history—and good meals—I bring walking shoes and my history-buff friend, John. We check into the 1898 Castine Inn.
“Some visitors find Castine a bit too quiet,” acknowledges owner Tom Gutow the next morning as we devour blueberry pancakes in his mural-wrapped dining room. “And others love it for just that reason.”
During our after-breakfast stroll down to the waterfront, John explains that peninsular Castine, between the mouth of the Penobscot River and a deep harbor opening to Penobscot Bay, has been a much-contested strategic prize for centuries. One battle lives in infamy. In 1779, when the British moved in, an American fleet sailed out of Boston to roust them. But the revolutionists got bottled up in the river and had to burn their own ships and walk home. “The worst defeat in U.S. naval history!” proclaims John.
Today the biggest ship in sight is the 500-foot State of Maine, a training vessel operated by the town’s Maine Maritime Academy. It towers beside the town dock, slapped by the wakes of passing runabouts and sailing yachts. If Castine has a tourist center, it’s this dock, complete with a lobster-roll shack (The Breeze) and the popular Dennett’s Wharf restaurant. John permits me a prowl through the gift shop, book shop, and art gallery before we set off on a hike to Dyce Head, the rocky tip of the peninsula.
Along the way, John reads the historical signs. One can’t take a step here without finding some tale of massacre or the site of a vanished fort. Take Fort Pentagoet. A French trading post in 1613, it switched hands nine times among the English, French, and Dutch during the next 130 years.
We walk down a woodsy path past a decommissioned lighthouse, and arrive at a cliff where waves crash on ledges far below. A bell buoy clangs. Two ospreys glide overhead. From here it feels as though the whole peninsula is sailing into greater Penobscot Bay.
That evening we dine elegantly at Pentagöet Inn, where I enjoy delicious local crab cakes followed by scallops on asparagus risotto. Then John, surprisingly, snaps into the present tense. “How about some after-dinner jazz at the Castine Harbor Lodge?” he suggests. “Or,” he adds, scanning a list of events plucked from the inn desk, “there’s a novelist reading at the Unitarian Church. And tomorrow, I’d love to catch that lecture on Sir Francis Drake at The Wilson Museum.”
While John enjoys his lecture, I take my first sea kayaking lesson with Karen Francoeur. A master Maine Guide, she’s a stickler for safety. Soon she has us skimming along the shore as she points out the sites of things long gone: a rope walk, a customs house, a sardine factory. In Castine, even afloat, I’m paddling into the past.
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