Boothbay Harbor

Lia and I got to Boothbay Harbor a little past noon, and the first thing I did — before finding our room, before even looking for coffee — was walk out onto the footbridge. It’s a strange, wonderful thing, this narrow wooden crossing built in 1901, stretching straight across the harbor so pedestrians could get from one side to the other without walking the long way around. Lobster boats were coming in below us, engines idling, gulls working the wake, and I remember thinking that this town calls itself the “boating capital of New England” and, standing there, I believed it without needing convincing.

We were staying in a small inn a five-minute walk from the footbridge, and every morning I’d wake up early and go sit on the dock with a cup of coffee, watching the fog burn off the water. Boothbay started as a shipbuilding and fishing town in the 1800s, and even now, with the gift shops and the ice cream stands, you can still feel that working-harbor bones underneath it all — the smell of diesel and salt, the guys hauling traps at six in the morning while the rest of the town was still asleep.

One afternoon we drove out to the Coastal Maine Botanical Gardens, which turned out to be one of those places that’s much bigger than you expect — nearly 300 acres along the Sheepscot River, and we only managed to cover a fraction of it before our feet gave out. Lia kept stopping at every turn to photograph something: a fern garden, a reflecting pool, a stone bridge half-covered in moss. I’m not usually a garden person, but I’ll admit I lost track of time there. We ended up eating cheese and crackers on a bench overlooking the river instead of going back for a proper lunch, and neither of us minded.

We happened to be there during Windjammer Days, which has apparently been running since 1963, and the harbor filled up with these enormous old tall ships, sails up, drifting in past the footbridge. I stood on the bridge again that evening, this time with half the town around me, and watched the ships anchor for the night while someone nearby explained to their kid what a windjammer actually was. It felt like the whole point of the town distilled into one evening.

When to go: Aim for June through September — the water’s at its warmest for boat trips, the footbridge is at its liveliest, and if your timing lines up with Windjammer Days, even better.