Boston North Shore Historic Harbors

Waypoint introductions and full write-ups

1. 1. Boston

   Boston is a compact old city with an unusually long memory. It was founded in 1630 by Puritan settlers on a small peninsula, and by the 1770s it was the centre of the colonial protest against British rule, with the Tea Party, the Massacre and the first battles of the Revolutionary War all taking place within a few days' ride. The Freedom Trail, a red line painted on the pavement, links sixteen historic sites, from the Old State House to the Old North Church, and it is a simple way to see the old core on foot.

   Read the complete Boston write-up.

2. 2. Salem

   Say Salem to an American and the answer is 1692. That year, in the grip of fear and bitter local feuds, a court in this small Massachusetts seaport condemned nineteen people to hang for witchcraft, and another man, Giles Corey, was pressed to death under stones for refusing to plead. The trials ended within a year, and in the decades afterwards the colony openly regretted them. Today the town leans into the story with witch museums, costumed guides and shops selling crystals, and in October it fills with so many visitors that the streets nearly seize up.

   Read the complete Salem write-up.

3. 3. Marblehead

   Marblehead is a harbour town in the old sense, a crooked tangle of lanes and clapboard houses crowded around a bay full of masts, founded in 1629 on a rocky peninsula that never offered any farmland and so turned to the sea. About twenty thousand people live here, and the streets of the Old Town are the reason to come: narrow, steep, bending at odd angles between houses built when carts were the only traffic. Salem, a bigger neighbour famous for its witch trials, lies a few kilometres to the north-west, and for riders it is the place for fuel and plentiful parking.

   Read the complete Marblehead write-up.

4. 4. Manchester-by-the-Sea

   Manchester-by-the-Sea is a small town on Massachusetts's North Shore, a place of about five thousand people on the southern flank of Cape Ann, and it has the look of a New England postcard. White clapboard houses, a harbour full of small boats and a stone-walled park on the waterfront give it a tidy, old-fashioned charm. The town was called Manchester until 1989, when residents added the words by-the-Sea to avoid confusion with the New Hampshire city, and the 2016 film that borrowed the name made it known around the world.

   Read the complete Manchester-by-the-Sea write-up.

5. 5. Gloucester

   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.

   Read the complete Gloucester write-up.