MILES 10-14: Rye Harbor  

I stay in the Gilded Age for a few more miles until the mansions turn back into cottages and the path into a pebbly beach with a high berm to keep storm tides at bay. I cross into Rye, where barnwood houses look extra cozy: Think tree houses that have been spruced up with gables and decorative paint jobs and brought down from branches to dunes, and given names. “Rye on the Rocks,” says one, a few doors from “The Catcher’s Lair.”

I pass bobbing boats anchored in Rye’s state marina. This is the place to catch whale-watching tours, which head a dozen miles out to sea to spot humpback, finback, and right whales. Others come for a ferry serving Star Island, a summer retreat more than a century old.

Left: Art exhibit, New Castle