Cape Ann Loop

Scenic road chapters

Waypoint introductions and full write-ups

1. 1. 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.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   Gloucester sits at 0 km, early in the day. Next is Rockport.

2. 2. Rockport

   Rockport sits at the tip of Cape Ann, on the Massachusetts coast north of Boston, and it is a town that lives by granite and by its looks. A red fishing shack on a wharf in the harbour, known as Motif Number 1, has been painted and photographed by so many artists that it is often called the most painted building in America, and a visit to the quay at dawn, with fishing boats and lobster pots in the light, shows why. The town's streets are lined with galleries and shops, and a stone breakwater curves out into the water.

   Read the complete Rockport write-up.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   Rockport comes up 10 km in. Next is Manchester-by-the-Sea.

3. 3. 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.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   20 km in you reach Manchester-by-the-Sea. Next is Gloucester.

4. 4. Gloucester

   Return visit. Read the place description above.

   Read the complete Gloucester write-up.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   Gloucester, late in the day.

Recorded source links

Source