This Massachusetts cape has a beach where the sand squeaks and a house built from newspapers

Four towns with squeaking sand and a paper house

Thirty miles north of Boston, the land runs out into a rocky hook that juts into the Atlantic.

Cape Ann holds four towns, the oldest seaport in the country, and a beach where the sand talks back when you walk on it.

There’s a castle on a cliff, a house built from 100,000 newspapers, and a red shack that painters won’t stop drawing.

You’ll want more than a day.

Four towns linked by one coastal road

You can drive the whole of Cape Ann in under an hour, but nobody does. Gloucester, Rockport, Essex, and Manchester-by-the-Sea each have their own feel.

Gloucester works the water. Rockport paints it. Essex trades in antiques and fried clams. Manchester keeps to itself.

The Essex Coastal Scenic Byway stitches them together, winding past harbors, marshes, and stone walls.

If you leave the car behind, the MBTA commuter rail from Boston drops you in Gloucester or Rockport in about an hour.

Gloucester has worked the water since 1623

Gloucester started as a fishing outpost in 1623, when English settlers from Dorchester pulled ashore and stayed.

That makes it the first permanent European settlement in Massachusetts, four centuries of boats leaving the same harbor.

The town became official in 1642, and the fleet still heads out every morning. Downtown keeps its old brick and clapboard fronts, with no rebuilt cuteness to get in the way.

Stage Fort Park marks the exact rocky shore where those first settlers stepped off.

The bronze man gripping a ship’s wheel

On Stacy Boulevard, a bronze fisherman in a storm slicker grips a ship’s wheel and stares out at the harbor.

Sculptor Leonard Craske made him for Gloucester’s 300th anniversary, and the town unveiled the statue in 1923.

The inscription reads, “They that go down to the sea in ships.” Plaques nearby list thousands of Gloucester fishermen who never came back.

A companion statue honors the wives and families who stayed behind, waiting for boats that were already gone.

The most painted building in America

A red fishing shack sits on Bradley Wharf in Rockport Harbor, and painters won’t leave it alone.

Art teacher Lester Hornby kept catching his students drawing the same building and started calling it Motif No. 1.

The name stuck. The original shack went up in the mid-1800s to hold fishing gear, and a 1978 blizzard knocked it flat.

The town rebuilt it the same year, board for board. A local lobsterman has leased and cared for the shack for decades.

Bearskin Neck and the bear that named it

Bearskin Neck is a narrow finger of land that pokes out from downtown Rockport into the harbor. Local legend says the name came from a bear killed there around 1700, its hide left to dry on the rocks.

The first dock went in by 1743, and the neck grew into a center for fishing and shipbuilding. Today the lanes are tight and packed with small shops, galleries, and seafood joints.

No chains. Walk to the jetty at the tip and you’ll see Sandy Bay wide open in front of you.

The inventor’s castle on a Gloucester cliff

John Hays Hammond Jr. held more than 400 patents and earned the title Father of Radio Control, then spent 1926 to 1929 building himself a stone castle on a Gloucester cliff.

He pulled in pieces of medieval and Renaissance buildings from across Europe and stitched them into one place.

A drawbridge fronts the entrance.

The Great Hall holds a pipe organ Hammond built by hand. Out in the courtyard, an indoor pool sits under a system that can make fog and rain on command.

A flooded quarry at the coast’s edge

Halibut Point State Park wraps around the old Babson Farm Quarry at the northern tip of Rockport.

The pit is full of clear water now, but for decades men cut Rockport granite here and shipped it out to build bridges, tunnels, and city streets across the country.

The Cape Ann granite industry crashed in 1929 and never came back. Massachusetts bought 56 acres in 1981 and turned the ruins into a park.

On clear days, you can see Mount Agamenticus in Maine.

Sand that squeaks when you walk

Singing Beach in Manchester-by-the-Sea runs half a mile and makes a sharp squeak under your feet. Small, round quartz grains rubbing against each other cause the sound, but only when the sand is dry.

Wet, it goes silent. Henry David Thoreau stopped by once and walked away unimpressed. From the Manchester train station, the beach is about a half-mile walk.

The town liked the name enough to make it official, adding “by-the-Sea” in 1989 to separate itself from every other Manchester on the map.

A summer home built from 100,000 newspapers

In 1922, engineer Elis Stenman started gluing together a summer home in Rockport’s Pigeon Cove neighborhood out of about 100,000 newspapers.

The walls are 215 layers thick, held together with flour and apple-peel glue, then rolled and varnished. Almost every stick of furniture inside is also rolled newspaper.

One desk was built entirely from papers covering Charles Lindbergh’s 1927 flight across the Atlantic. A hundred years later, the house is still standing, and you can wander through it on a self-guided tour.

Winslow Homer painted here and so did you

Rocky Neck pokes into Gloucester’s Inner Harbor on a small rocky point, and artists have been working there since the 1840s.

That makes it one of the oldest art colonies in the country. Winslow Homer painted on Cape Ann. So did Edward Hopper.

So did Fitz Henry Lane, born in Gloucester in 1804 and later one of the leading American marine painters.

Small galleries and working studios still fill the streets. The Cape Ann Museum downtown holds the largest collection of Lane’s paintings.

Whales feed 12 miles off the coast

Gloucester sits closer to prime whale feeding grounds than any other Massachusetts port.

Boats run out about 12 miles to Stellwagen Bank, a stretch of shallow ocean floor that became a National Marine Sanctuary in 1992.

Humpbacks breach. Finbacks slide past. Minkes surface near the boat. The season runs May through October, when the whales come up to feed on schooling fish.

Trips also swing past Gloucester’s lighthouses and the rocky stretches of shore where fishing boats have been hugging the coast for 400 years.

The town that fried the first clam

Essex is the inland town of Cape Ann, threaded with salt marshes and quiet roads.

In 1916, Chubby and Bessie Woodman dropped a clam in hot fat on the 4th of July and served it to a holiday crowd. The idea caught fire.

Woodman’s of Essex still runs on Main Street more than a century later.

The town also has one of the highest counts of antique shops per square mile in the country. At the Essex Shipbuilding Museum, you can walk through its wooden-boat past.

Plan a trip to Gloucester, Massachusetts

You’ll want to base yourself in Gloucester, the biggest and oldest town on Cape Ann and about an hour by car or MBTA commuter rail from Boston.

Good Harbor Beach and Wingaersheek Beach are both within city limits, and the harbor, museums, and Hammond Castle sit a short drive apart.

Check the official websites for current hours and admission, especially for Hammond Castle and the Cape Ann Museum, since both run on seasonal schedules.

Pack layers. The coast gets cold fast once the sun drops.

This article was created with AI assistance and human editing.

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• America’s most painted building is a red shack in Rockport, Massachusetts
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