Cape Ann is the other Cape of Massachusetts — the one that doesn’t get the same breathless coverage as Cape Cod but arguably offers just as much, with a more authentic feel and fewer crowds. Situated about 30 miles north of Boston, Cape Ann is home to two of the most distinctive small cities on the New England coast: Gloucester, a working fishing city with a long and storied history, and Rockport, a quiet artists’ colony with one of the most picturesque harbors in America.
Gloucester: America’s Oldest Fishing Port
Gloucester was founded in 1623, making it the oldest fishing port in America. That history is everywhere you look — in the bronze Fisherman’s Memorial statue on Stacy Boulevard (dedicated to the more than 10,000 Gloucester fishermen lost at sea), in the working waterfront where commercial fishing boats still come and go, and in the unpretentious, hardworking character of the city itself.
But Gloucester isn’t just history. It has some genuinely excellent beaches. Good Harbor Beach is one of the finest sandy beaches on the entire North Shore — wide, clean, and backed by low dunes, with a small tidal island you can walk to at low tide. Wingaersheek Beach, on the Annisquam River, is a favorite for families with young children: calm, shallow water and dramatic views of the Annisquam lighthouse across the channel.
The downtown arts district along Main Street and Rocky Neck — the oldest working artists’ colony in America — has galleries, studios, and restaurants that punch well above what you might expect from a city of Gloucester’s size. Rocky Neck in particular, a small peninsula jutting into Smith Cove, has a funky, creative energy that’s unlike anywhere else on the North Shore.
Rockport: Small, Beautiful, and Unforgettable
Just six miles from Gloucester, Rockport feels like a completely different world. Where Gloucester is a working city with rough-around-the-edges charm, Rockport is meticulously pretty — a village of narrow streets, shingled cottages, art galleries, and independent shops clustered around one of the most photogenic harbors in New England.
Bearskin Neck, the main commercial street, juts out into the harbor on a narrow spit of land lined with small shops and restaurants. At the end of the Neck sits Motif Number 1 — a red fishing shack that has been painted by so many artists over so many decades that it earned the nickname “the most often painted building in America.” It’s genuinely charming rather than contrived.
Rockport’s beaches are rocky rather than sandy — Front Beach and Back Beach in the village are pleasant for a swim, but the real draw is Halibut Point State Park, about two miles north of the village center. The park’s rocky headland offers dramatic views of the open Atlantic, a fascinating old granite quarry that has flooded into a swimming hole, and walking trails through coastal scrub. It’s one of the best half-day hikes on the North Shore.
🗺️ Getting to Cape Ann
Cape Ann is about 45 minutes from Boston by car. The MBTA commuter rail runs from North Station in Boston to Gloucester and Rockport — a scenic, easy ride that drops you right in the heart of each town. Taking the train is highly recommended; parking in Rockport especially can be challenging in summer, and the train ride along the coast is genuinely enjoyable.
🎯 Things to Do on Cape Ann
Cape Ann packs a remarkable range of activities into a small peninsula — from world-class whale watching to granite quarry hikes to gallery-hopping on Bearskin Neck.
Whale Watching — Cape Ann Whale Watch and Seven Seas Whale Watch both depart from Gloucester Harbor. Humpbacks, finbacks, and minkes feed on nearby Stellwagen Bank from spring through fall. These trips are genuinely world-class.
Halibut Point State Park — At the northern tip of Rockport, this park features dramatic granite quarry views, tidal pools, and one of the finest ocean vantage points on the Massachusetts coast. Bring a picnic.
Bearskin Neck — Rockport’s famous pedestrian lane is packed with art galleries, boutiques, and seafood shacks. Walk it end-to-end and grab a lobster roll with harbor views at the pier.
Good Harbor Beach and Wingaersheek Beach — Gloucester’s two signature beaches offer wide sand and calmer crowds than South Shore beaches. Both are great for families.
Cape Ann Museum (Gloucester) — An underrated gem covering the maritime history of America’s oldest fishing port, with a major collection of Fitz Henry Lane marine paintings.
🎯 Browse whale watching and tours on Cape Ann on Viator →
🍽️ Where to Eat on Cape Ann
Gloucester’s seafood is about as fresh as it gets — this is a working fishing port, after all. The Franklin Cape Ann is one of the best restaurants in the region, with creative New American cooking in a relaxed setting. For more casual seafood, Latitude 43 on the harbor is excellent. In Rockport, My Place By the Sea has beautiful harbor views and reliably good food; the Roy Moore Lobster Company is a classic raw bar with lobster, clams, and cold beer right on the harbor.
Cape Ann is a genuine four-season destination, but summer and early fall are the sweet spots for beach visits. The Gloucester Schooner Festival in early September is one of the best maritime events in New England, with tall ships racing in the harbor. The Rockport Art Association hosts shows and events throughout the summer. And the fall foliage adds another layer of beauty to an already gorgeous landscape.
Cape Ann vs. Cape Cod: Which Should You Choose?
It depends on what you’re after. Cape Cod offers longer sandy beaches, warmer water, and a broader range of accommodation options. Cape Ann offers more authentic New England character, easier access from Boston, a stronger arts scene, and the feeling that you’ve found somewhere slightly off the beaten path. Many visitors who discover Cape Ann end up preferring it — and returning every summer.
⛵ Day Trip Idea: Just an hour away, the Boston Harbor Islands offer beautiful beaches, a Civil War fort, and stunning skyline views — all 30 minutes by ferry from downtown Boston.