The heart of Cape Ann, a storied Fishing community with equal parts glitz and grit

Gloucester’s reputation as a major fishing port on Boston's North Shore is well-deserved. Despite smaller hauls from a diminished fleet, its famously well-protected harbor remains at the heart of this 400-year-old community. Development pressures continue to reshape the city, but it is not in immediate risk of morphing into Newport North – the city saw to that in 1972 when it regulated development along its waterfront to include only the commercial fishing industry. As a result, Gloucester’s harbor is lined with fish processing plants – some busier that others – marinas, Gloucester Cruiseport, wholesale and retail seafood stores and a number of good restaurants. Its brick-lined Main Street is a short stroll from the harbor and is well worth poking around. You will find it hard to resist browsing through a bookshop, finding a one-of-a-kind fashion statement, grabbing a Cappuccino or leafing through a few thousand vintage vinyl albums. 

Gloucester celebrates its idiosyncratic history at several museums, including the Cape Ann Museum, or CAM for short, Hammond Castle, built to fulfill a boyhood dream, weird and wonderful Beauport on Eastern Point, compact Maritime Gloucester on the waterfront and the post-revolutionary Sargent House perched regally over Main Street.

But wait, there’s more

Gloucester encompasses surprisingly varied neighborhoods, topography and shoreline, from the quiet villages of Annisquam, Lanesville and Magnolia to woodsy Dogtown and Ravenswood Park to the pristine sands of Good Harbor Beach and the surf-scoured rocks of Atlantic Road.

If you find yourself in downtown Gloucester, be sure to stroll down Stacy Boulevard to view the Gloucester Fisherman’s Memorial. On a summer day, continue past the Memorial and wait for the drawbridge to open on the southern end of the Blynman Canal. The narrow ‘cut’ beneath the bridge is a source of entertainment as vessels small and large negotiate the standing waves and narrow-walled passage.

For a more extended walk, cross the ‘cut’ and stroll along the newly-constructed waterfront walk to Stage Fort Park and climb up the rocks on your left for magnificent views of the city and the outer harbor, looking across to Eastern Point and Ten Pound Island.

There’s plenty more to explore in Gloucester so let’s get going!