eXp Realty Kathleen Militello, Realtor® The Militello Team COASTAL HOMES & LIVING

Town notes · 2026-09-20 · 5 min read

Cape Ann: Gloucester, Rockport, and Essex

Cape Ann is the working heart of the North Shore: Gloucester's harbor, Rockport's studios, Essex's clam shacks and shipyards. Each town has its own character, and together they make some of the most distinctive coastal living in New England.

A Gloucester-style harbor village at dusk with warm lit windows above the water

Gloucester: a working harbor, and an artist's light

Gloucester is America's oldest seaport, and it still works like one: the harbor fills with working fishing boats, the waterfront smells like salt and diesel, and the catch comes in daily. That authenticity is exactly why people love it. It is a real town with real industry, not a postcard.

The same harbor light that feeds the fleet drew artists for generations. Rocky Neck, across the water from downtown, is one of the oldest working artist colonies in the country, and studios still open their doors to visitors. Gloucester manages to be gritty and beautiful at the same time, which is a hard combination to find.

Rockport: a studio by the sea

Rockport started as a granite town and remade itself as an art colony. Bearskin Neck, the narrow stone peninsula at the harbor, is lined with former fishermen's shacks turned galleries and shops, and the little red fishing shack on the wharf is said to be one of the most painted buildings in America.

Rockport lives at a slower pace. Front Beach and Long Beach are long-standing favorites in the summer, and the year-round residents keep the village real when the crowds leave. It is a small town, and it knows it.

Essex: shipbuilders and the fried clam

Essex built ships. Its yards launched thousands of wooden vessels over the centuries, a tradition the Essex Shipbuilding Museum keeps alive, and the town still hugs the river that made it possible.

It also gave the world the fried clam: Woodman's of Essex fried the first one in 1916, and the shack still draws lines out the door in season. Between the river, the marshes, and the clam shacks, Essex is the North Shore in its most honest form.

Places I send people

  • Seaport Grille

    Gloucester seafood with a view of the working harbor; a reliable place to take out-of-town buyers.

  • 1606 Restaurant & Oyster Bar

    Raw bar and waterfront dining on Commercial Street, right in the heart of the harbor.

  • Lobsta Land

    Causeway seafood favorite that does the classics the way the coast intends.

  • Woodman's of Essex

    The original fried clam, still going strong just off Route 133. A North Shore rite of passage.

Cape Ann buyers tend to know what they want: light, water, and a real town around them. I can help you sort which of the three fits you best.

Coastal Communities

Gloucester, MA: a full community page

The working harbor, the villages from Annisquam to East Gloucester and Magnolia, the beaches, and the town's real estate character, in Kathleen's own words.

Read about Gloucester
Kathleen Militello, Realtor

Written by

Kathleen Militello, Realtor®

More than 20 years on Boston's Coastal North Shore with eXp Realty. Read her story.

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