Eastern Point Lighthouse.

There are few ports saltier than Gloucester, a city famous for fishing. From cod and herring to tuna and swordfish, all manner of North Atlantic finfish have been landed and processed in this busy harbor on Cape Ann since English settlers arrived in 1623.

Although the fishing industry did not truly flourish here until the mid-1800s (inland logging and farming were the chief pursuits of early Gloucesterites), the image of the rugged “Gloucester Fisherman”—forever clad in his sou’wester hat, black boots, and yellow oilskins—eventually became the romanticized and enduring symbol of Gloucester. Thanks in large part to Gorton’s, the company founded in Gloucester more than 150 years ago and credited with developing frozen seafood products, the image is known throughout the world.

While Gloucester’s pride in its fishing heritage runs deep, a steady decline in cod stocks, coupled with strict fishing regulations and an aging workforce, produced a steep decline in the commercial groundfishing fleet, which shrank by almost 20 percent between 2003 and 2008. In response, the city made an effort to attract more recreational boaters by renovating its working-class waterfront with an educational HarborWalk trail, several dock-and-dine options, museums, unique boutiques, a five-star hotel and, perhaps most important, expanded marine facilities that make it easier for visiting boaters to tie up and experience the revitalized downtown area.

Gloucester Boating

Transient moorings can be arranged via the harbormaster’s office in both the outer and inner harbor. For DIY boaters, the best anchorage in the former is Southeast Harbor, which features a soft mud and clay bottom with depths of 23 to 30 feet. Western Harbor is a good option in westerly or northerly winds. A launch delivers boaters to the three primary public landings, all within minutes of downtown, or to the waterfront establishment of their choice.

Tarr and Wonson’s Copper Paint Factory is at #14 on the Harborwalk.

Boaters who prefer a slip can contact one of Gloucester’s local marinas. The largest is Cape Ann’s Marina Resort, which caters to transients and offers a host of amenities, including a fuel dock, pool, restaurant, and bar.

This marina and the nearby Gloucester Marina are situated on the protected Annisquam River, which connects to the Western Harbor via the Blynman Canal, and essentially places Gloucester on an island. The Annisquam-Blynman route also serves as a shortcut between Gloucester Harbor and Ipswich Bay for cruisers who use Gloucester as a stopover on their way north or south.

HarborWalk and Restaurants

Once docked or moored, boaters are minutes from a bustling waterfront and downtown filled with hip restaurants, historic buildings, art galleries, and shops. Exotic waterfront homes built in the 19th century have been transformed into museums and popular historic attractions, such as Beauport, Hammond Castle, and the Sargent House. The HarborWalk—a series of granite signposts—guides visitors along a free, interpretive walking tour of Gloucester’s waterfront and downtown district.

If you’re hungry, the waterfront offers myriad options, for boaters and landlubbers alike. One of the most popular dock-and-dine spots is Mile Marker One at the aforementioned Cape Ann’s Marina Resort. Bands perform on the so-called “bridge deck,” and the bar specialty is a mean Pain Killer cocktail.

Elsewhere on the harbor, the quirky Latitude 43 is the place to go for sushi lovers and live music, while Passports offers classic seasonal seafood dishes and New American cuisine sourced daily from the Atlantic.

‘The Beautiful Harbor’

Visitors who want to learn more about Gloucester from the water can explore the entire harbor aboard the local water shuttle, while two wooden schooners, the Ardelle and Lannon, offer daytrip sails and tours. A replica 19th century “Pinky” schooner built in nearby Essex, the 45-ton Ardelle is a reminder of Gloucester’s shipbuilding past.

In 1605, explorer Samuel de Champlain christened Gloucester, “the beautiful harbor,” and its natural splendor continues to attract both land- and waterborne visitors centuries later. Today, Gloucester is an amalgamation of working waterfront and vibrant tourist destination, and for transient boaters, the welcome sign is very much on display.