Gloucester claims to be America's oldest seaport, settled in 1623, and the town has been pulling fish out of the Atlantic ever since. It sits on Cape Ann, the granite thumb that sticks out of Massachusetts north of Boston, where the coast is a tangle of coves, boulders and working harbours instead of the long sandy beaches farther south. The bronze fisherman at the wheel on the waterfront, put up in 1925, looks toward the sea with the words about those who go down to it in ships, and the memorial lists thousands of local names lost over the centuries. Sebastian Junger's book The Perfect Storm, set among a Gloucester swordfish crew, made that grief known to the rest of the world.
The town has also been an artists' harbour. Winslow Homer painted here in the 1870s, Edward Hopper came for the light, and the Rocky Neck colony still runs on that tradition. Granite was the other great industry. Quarries on Cape Ann supplied stone for buildings and paving up and down the coast, and abandoned pits now fill with water that locals swim in. You see the stone in the sea walls, the gate posts and the rock that comes through the lawns.
Riding Cape Ann is a short, slow and rewarding loop. Route 127 follows the shore, past Magnolia, Rockport and Annisquam, in a series of tight, tree-lined bends with glimpses of the ocean and lobster buoys hung on shed walls. Roads are narrow and potholed after the winter, and in summer weekends traffic crawls, especially around the beaches and Rockport's Bearskin Neck, so aim for a weekday morning or an autumn day, when the maples go red and the crowds thin. The fog can roll in quickly, cooling the air by ten degrees.
Gloucester has fuel and everything else a traveller needs. Fried clams and lobster rolls are the staples, and the Italian bakeries and sandwich shops reflect the Sicilian and Portuguese fishing families who settled here. At the end of the day, find a spot on Eastern Point near the lighthouse and watch the boats come in as the light drops.