Down to the Sea: Gloucester, MA

Famous as a fishing port, the city of Gloucester plans to draw more attention from boaters with a revitalized waterfront and expanded marine facilities.

By Rob Duca | Photography by Benjamin Boynton
*Pictured above: Downtown Gloucester as viewed from Stage Fort Park.

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.

A speedboat makes it way through the Blynman Canal and Annisquam River.

New Directions

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 has produced a steep decline in the commercial goundfishing fleet, which shrank by almost 20 percent between 2003 and 2008. In response, the city has made an effort to attract more recreational boaters by renovating its working-class waterfront with an educational HarborWalk, 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

The city offers some 35 transient moorings for visiting boaters. These can be found in both the outer and inner harbors, including 15 in Southeast Harbor, five off Stage Head in Western Harbor, and nine in the Inner Harbor. For those who wish to anchor, the best anchorage in the outer harbor 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 26-passenger launch delivers boaters to the three primary public landings, all within minutes of downtown, or to the waterfront establishment of their choice.

The Cape Ann’s Marina Resort welcomes transients with a host of amenities.

Slip In

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

The marina, as well as nearby Gloucester Marina, is situated on the protected Annisquam River, which connects to 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.

Downtown Delights

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 informative granite signposts—guides visitors along a free walking tour of Gloucester’s waterfront and downtown district, including public art exhibits, gardens, scenic views and special events.

If you’re feeling hungry, the downtown area offers myriad options, for boaters and landlubbers alike. One of the harbor’s most popular dock-and-dine spots is the Mile Marker One restaurant, 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. Captain Carlo’s, on the working waterfront, is owned by Gloucester natives and has a sparkling reputation for fresh seafood. The quirky Latitude 43 is the place to go for sushi lovers and live music, while Passports offers classic seasonal seafood dishes sourced daily straight from the Atlantic.

History Abounds

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. “A major part of the city’s heritage is that it produced 3,000 schooners for the fishing fleet in the 1800s,” points out Ken Riehl, CEO of the Cape Ann Chamber of Commerce.

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.

The Fisherman’s Wife Memorial stands watch over the harbor.

Gloucester Names & Numbers


(978) 282-3013

Dockage, Moorings & Service

Cape Ann’s Marina Resort
(978) 283-2116;

Deep-water transient slips, moorings and dockage for boats up to 100 feet. Also offers a fuel dock, onsite restaurant, pool, laundry, showers, ice, bait, WiFi, repair and more.

Gloucester Marina
(978) 283-2828

On the Annisquam River; offers transient slips, gas and repair. Fifteen feet MLW.

Enos Marine & Pier 7 Marina
(978) 281-1935

Transient slips and moorings for boats up to 120 feet, ice, cable, power, water and service. On the inner harbor.


Good holding ground in 20 to 30 feet of water can be found in Southeast and Western Harbors, just outside the inner harbor.

Launch Ramp

A free public launch facility with ample parking can be found adjacent to Gloucester High School, opposite the Cape Ann’s Marina, on the Annisquam River. This is a two-lane ramp, and features a float.

Where to Eat

Mile Marker One
(978) 283-2116;

Dock-and-dine restaurant and bar at the Cape Ann’s Resort Marina.

Latitude 43

(978) 281-0223;

Seafood and sushi with great harbor views.

The Rudder
(978) 283-7967;

Dock-and-dine restaurant on Smith Cove. Specializes in creative seafood dishes in a fun, festive atmosphere.

Duckworth’s Bistrot
(978) 282-4426;

French-inspired, small-plate portions.

Seaport Grille
(978) 282-9799;

Wide menu of surf-and-turf dishes, plus pizza, burgers and signature drinks.

Cape Ann Brewing Co.
(978) 282-7399;

Family-owned brewery/eatery serving craft ales and pub fare. Also offers tours, concerts and a waterfront deck.

The Studio
(978) 879-4896;

Enjoy sushi, shellfish, tapas and live music on the waterfront deck of this casual dock-and-dine restaurant on Smith Cove.

Cool Shops

Dress Code
(978) 281-2888

Consignment boutique carrying a plethora of fun things, from vintage clothing and shoes to home décor items.

The Cave
(978) 283-0896;

Wide selection of fine cheeses and bread, as well as salted caramel, wine and chocolate.

Holy Cow Ice Cream Café
(978) 281-0313;

Sample ice cream tacos, ice cream cannolis, giant ice cream Oreo sandwiches and more at this palace of frozen delights on Pleasant Street.

Mystery Train Records
(978) 281-8911;

Rare and collectible recordings, including LPs, 12- and 10-inch singles, 45’s, 78’s, 8-track tapes and CDs.

Things to See & Do

Schooner Ardelle
(978) 290-7168;

Tour the waters off Cape Ann aboard a wooden Pinky schooner built in Essex.

Maritime Gloucester
(978) 281-0470;

Explore Gloucester’s long relationship with the sea via interactive, hands-on exhibits, touch tanks, aquariums, fishing gear displays, a giant lobster trap and more.

Gloucester HarborWalk

Follow this self-guided walking trail defined by 42 granite story posts installed as a permanent exhibit. Each marker highlights an aspect of Gloucester’s history as a seaport, its rich culture and people, and its evolution toward a modern, sustainable fishing industry.

Cape Ann Museum
(978) 283-0455;

Intimate museum featuring maritime and fine-art collections, along with exhibits and artifacts relating to the history and culture of Cape Ann.

Gloucester Schooner Festival

Held Labor Day weekend, this event is a gathering of glorious schooners from all parts of New England. A highlight is the Parade of Sail, during which participating schooners make their way through the harbor and out past the breakwater, before ending at the Mayor’s Race starting area off Eastern Point.

Sargent House Museum
(978) 281-2432;

Visit this Georgian-style house built in 1782 and learn about the early history of Gloucester from its beginnings as a farming and lumbering outpost to its evolution into the country’s premier seaport. Also features a collection of original works by portrait painter John Singer Sargent, a descendant of the Sargent family.

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