Rockin’ around the clock

The commercial fishing vessel Miss Carla in Western Harbor, the spire of Gloucester City Hall in the background.

Story and photos by Marilyn Pond Brigham
For Points East

Mariners are, by rights, wary of rocks, and those cruising to Gloucester, Mass., need to be particularly cautious all around that great harbor because there are so many of them. Many hazards, most well-marked, exist from Ragged Ledge to Popplestone, to Normans Woe Rock, Round Rock Shoal, Prairie Ledge and Field Rocks, Babson Ledge and Black Rock, Rocky Neck, Mayflower Ledge, Tenpound Island Ledge, Black Bess Rocks, Round Rock Shoal and Dog Bar Channel to Eastern Point Ledge.

From Boston’s North Shore, one approaches Gloucester Harbor from Massachusetts Bay, cruising along a rugged coast and passing the affluent towns and villages of Beverly, Prides Crossing and Manchester-by-the Sea. It’s fun to gawk at the large homes and mansions that line the rocky precipices. Gloucester occupies much of Cape Ann, sharing it with the Town of Rockport. Gloucester is bisected to the west by the Blynman Canal and the Annisquam River. So, as we approach Gloucester Harbor, envision the shore around it as a clock face, and our cruise of its offerings and its rocks and hard places at the southwest corner, at a figurative 7:00.

Seven o’clock rock: On the westernmost point of Gloucester’s outer harbor, off the cliffs of the Gloucester village of Magnolia, lies the ominous Norman’s Woe Rock, inspiration for Herman Melville’s “The Wreck of the Hesperus.” This is the tragic tale of a skipper who ignores sound maritime advice and loses his ship, his life, and that of his lashed-to-the-mast daughter in a great storm.

Approach to Gloucester Harbor is by G “3” to G “7” off Prairie Ledge. While making your way there, you’ll see Hammond Castle ( to port. This is a dramatic medieval castle built in the 1920s by John Hammond, an inventor of remote-control through radio waves. As mariners, we are beholden to him, as his invention led to the development of radar, sonar, depthsounders and GPS. It is well worth your time to explore this fascinating place.

Nine o’clock rock: Cruising past Field Rocks and Tablet Rock, to port, is Stage Head. Once ashore, that area is a great place to explore on foot and get some exercise. Stage Head is home to Gloucester’s Visitor Center, where one can learn about all there is to see and do in Gloucester. It’s also the site of Stage Fort Park, a large and beautiful area with several beaches, playgrounds, walking trails, and a dog park. The first English settlers in 1623 erected fishing stages there, and, later, a fort to protect residents from the British. It’s fun to climb around the ramparts and old cannons that aim out over the harbor.

Eleven o’clock rock: Continue into the waters of Western Harbor, and you’ll be at the entrance to the Blynman Canal by RW “14” (BC). Here, you can see the 38-foot bascule span that leads into Gloucester’s main drag (Rte. 127). Locals call this the Cut Bridge, and be aware that southbound boats (those heading out of the canal) have right of way here. The bridge-tender monitors VHF Channel 13.

Through the bridge, it’s a straight shot to the Cape Ann Marina (, which has transient slips, and is a pleasing spot to stay for a couple of days while exploring Gloucester and the Annisquam River. The marina has everything one would expect, plus a hotel and pool, and is within walking distance of downtown Gloucester.

Twelve o’clock rock: Back out in Western Harbor, if you look toward downtown Gloucester, you’ll almost be able to make out the heroic gaze of the bronze fisherman statue, looking out over the harbor. That is the famous Gloucester Fisherman’s Memorial, dedicated to “they that go down to the sea in ships” and who have perished or been lost at sea.

Just off Fort Point, in downtown Gloucester, is Babson Ledge, at G “9”, which, along with R “10”, marks the entrance to the channel to the Inner Harbor. You’ll see the beautiful, new, Beauport Hotel, off Pavilion Beach. French explorer, Samuel de Champlain, called Gloucester “Beau Port” (beautiful harbor), and lots of things about town are called “Beauport.” You’ll be able to see the clock tower and the copper dome of City Hall, which dominates the town and harbor, and also the steeples of Gloucester’s churches. Once on foot, check out the Gloucester HarborWalk, a 1.2-mile self-guided tour through the working waterfront and historic downtown area.

One o’clock rock: Gloucester, America’s oldest fishing port, is still an active working harbor with fish piers, lobsterboats, trawlers, and a U.S. Coast Guard Station. Harbor Cove, off G “13”, can be explored on foot and on the water. We did both, but particularly enjoyed a tour in our tender. Though we felt mighty small with all those large vessels, the dinghy was much more maneuverable than our cruising sailboat, and we had fun poking about with it. Many public landings and tie-ups are in Gloucester, and, after our tour, we tied up at a dink dock at Gordon Thomas Park at the head of the Inner Harbor.

Both Birdseye Frozen Foods and Gorton’s of Gloucester had their beginnings in Gloucester, and both became national purveyors of frozen fish. The Inner Harbor is the real commercial section of Gloucester Harbor. The large State Fish Pier accommodates working boats, the Gorton’s fish-processing plant, the marine terminal for deep-sea fishing, and whale-watching boats. It also provides dockage for several restored fishing schooners.

We’ve taken on fuel at Brown’s Yacht Yard ( on the eastern side of the harbor; they also offer dockage and moorings for transients. Gloucester’s harbormaster ( maintains 31 transient moorings in both the outer and inner harbors, in Southeast Harbor, off Stage Head in the Western Harbor, and in Smith Cove in East Gloucester. Reservations can be made via Dockwa ( The harbormaster’s office has a launch service.

Two o’clock rock: With a harbor and surrounding landscape of such natural beauty, and many different kinds of boats plying its waters, it’s no wonder that Gloucester is home to America’s oldest working art colony on Rocky Neck. A veritable who’s-who of American artists – including native-son Fitz Hugh Lane – were inspired, and honed their talents, on this prominent site. We found a small boat ramp off Smith Cove where we could haul up the dinghy to walk around. We found artists at their easels painting en plein air, historic antique homes, small boutiques, and restaurants and ice-cream parlors to complete our Rocky Neck experience. A popular walking tour, with a descriptive brochure and map, lets you learn more about the area at your own pace and explore art galleries and artist studios.

Off R “10” and Black Rock, off the southwest corner of Rocky Neck, as you head back towards Gloucester Harbor, you’ll see the iconic 1880s Tarr and Wonson Paint Manufactory. Its distinctive, tall brick chimney brought many a Gloucester fishing vessel back into home port; and its famous copper bottom paint made vessels sail faster without the drag of marine growth. Production of paint had long ceased, and the building became derelict. However, now it’s renovated, and is home to the Ocean Alliance, an ocean research organization.

To warn mariners coming into the Inner Harbor of both Ten Pound Ledge and Mayflower Ledge to the southwest, Ten Pound Light was erected in 1821 on Ten Pound Island. The Island, a rocky ledge, is difficult to access via boat. However, during the summer of 1880, Winslow Homer bunked in with the light keeper and painted over 50 paintings of his impressions of the harbor.

Three o’clock rock: Southeast Harbor appears to have more moorings than rocks, but I’d still be wary. Here, homeowners have beautiful lawns and lovely views out over the harbor. Niles Beach, a stretch of sandy beach, is restricted to Gloucester’s resident sunbathers. Not far away is the fanciful mansion of one of the nation’s first professional interior designers, Henry Davis Sleeper ( He built his summer home, “Beauport,” in the early 1900s, and he filled it with exotic collections while theming each of the 56 rooms. It is preserved just as it was, as if he had just walked out the door.

Five o’clock rock: Farther along Eastern Point, past Black Bess Rocks, you approach another mooring field in Lighthouse Cove. Beyond that, and before the looming breakwater, is the almost century-old Eastern Point Yacht Club ( The club is located just before the Eastern Point Lighthouse, in a protected anchorage, and with a commanding lookout over Gloucester Harbor, Massachusetts Bay, and the Boston skyline.

There is no finer place for visiting cruisers on the North Shore. Eastern Point Y.C. has sheltered moorings, launch service, a lovely clubhouse, guest rooms and dining, a pool and the fellowship of mariners. We have enjoyed staying there many times. We particularly enjoy the club’s tradition of standing, hand over heart, beside your dinner table at dusk, when the cannon signals that the American flag is being lowered. Reservations can be made through Dockwa.

Another lighthouse was most necessary to guide vessels from the Atlantic, around Eastern Point Ledge and Webber Rock to Gloucester’s outer harbor, and on towards Salem and Boston. Ten Pound Island Light was only helpful to mariners already within Gloucester Harbor. Many vessels foundered at Eastern Point Ledge before they reached the wharves of Gloucester. Eastern Point Light was completed in 1832. The same summer Winslow Homer painted from Ten Pound Light, he also painted from this beacon. Alas, the Coast Guard actively maintains Eastern Point Light, and the public (artists included) are not able to visit.

Six o’clock rock: The 2,250-foot breakwater, Dog Bar Breakwater, was built by the Army Corps of Engineers in 1905 to protect the harbor from the fury of the Atlantic outside and the treacherous Dog Bar Reef just inside. A tower and light at the end of the breakwater was eventually installed, as vessels caught in inclement weather or darkness could sail right into the long structure, unaware of its presence. Today, it is also an appealing place for fishermen, who can be seen casting atop the huge granite blocks that cap the riprap below.

At the end of the breakwater is Dog Bar Channel – R “2DB” and G “1DB” – which leads out of Gloucester Harbor, past Round Rock Shoal RG “RR”. Once out of the channel, you are back in the briny deep, with 60 feet of water and only the occasional rock. However, if you want lots of rocks and a flood tide of maritime history, then go rock, rock, rock around Gloucester Harbor.

Marilyn Brigham and her co-captain/spouse Paul sail Selkie, a Catalina 445, out of Quissett Harbor, Falmouth, Mass. She is a lifelong sailor and a current member of both the Quissett and Cottage Park yacht clubs.