Gloucester has a vibrant shoreside community whose cultural origins span the maritime world. It's a particular favorite of ours when the weather turns dismal.


Gloucester’s magnificent natural harbor is easy to enter in any weather. European fishermen recognized its appeal in the early 1600s, and the evolution of the fishing industry has shaped the city over four centuries.

Since the mid 1800s, artists too have found inspiration along Gloucester’s shores. Harborscapes by Fitz Henry Lane and Winslow Homer are among the most important American marine paintings, and an active group of Cape Ann artists continue to paint in their wake.

Gloucester today has a vibrant shoreside community whose cultural origins span the maritime world. It’s a particular favorite of ours when the weather turns dismal.



Our first visit to Gloucester is still the most memorable. Chased in by a rising southeasterly and surfing the six foot waves that had turned us back from Provincetown, we arrived after dark. But the powerful light on Eastern Point is visible a long way off, a 45 foot tall red light clearly marks the end of the breakwater at the Dog Bar, and the entrance is otherwise free of obstructions. Once inside, the seas diminish steadily as the harbor narrows towards town. There are several good options for spending the night.

Not for navigation


Southeast Harbor, inside the breakwater and north of the Eastern Point Yacht Club mooring field, offers decent holding and protection from 3 sides. Depths stay in the high 20s until fairly close in to the beach, but there is plenty of room between 25 and 18 feet at low. And nice views of Ten Pound Island.

Western Harbor, in the upper left-hand corner of the outer harbor, can be a useful complement to the anchorage in lower right. It’s protected from southwest around to north, has depths in the teens relatively close to shore, and overlooks the attractive city-owned Stage Fort Park. Proximity to the Blynman Canal entrance does make for some concentrated traffic on busy weekends.

Within the inner harbor is a trapezoidal Anchorage Area between the North and South channels, and southwest of the line between nun “2” and can “3”. Depths are around 15 feet at low, and the bottom is mud. The channels on either side will be busy with fishing boats, but they usually go slowly enough that their wakes are only a minor nuisance. If you can accept a little commotion, anchoring here gets you the closest to the center of town.

📷 Geoff Rand
Eastern Point Light
📷 Geoff Rand
The quirky occulting light at the end of the Dog Bar breakwater is one of many red lights in the area. Inexperienced navigators sometimes confuse it with the much stronger red light on Thacher Island to the east.


Just inside the breakwater, Eastern Point Yacht Club maintains an extensive mooring field with 9 transient moorings. The moorings are first come, first served, but we’ve always found one open. The club offers launch service and facilities for visitors, but it is over two miles to town. The atmosphere tends to be quiet, although you may feel a little exposed. Call on 71 when you enter the harbor.

As you proceed up the harbor there are moorings, with increasing degrees of protection, around Ten Pound Island, beyond the Anchorage Area, and in Smith Cove. About 30 of these are city moorings, and may be reserved by calling the Harbormaster. Brown’s Yacht Yard has a few transient moorings in the Inner Harbor. All the moorings get busy during Gloucester’s several festival weekends.

Not for navigation


Brown’s also has a number of slips available for visitors, off of the south channel of the Inner Harbor. It’s a friendly place with a relaxed dockside feel. They take reservations, and suggest that availability is pretty good, with the exception of Labor Day weekend (Schooner Festival) which can book up a year in advance.

The most protected water, if not the quietest night, is found in Smith Cove, where the Madfish Bar and Grille and The Studio both offer dock space along with dockside dining. A little further in, low-profile Bickfords Marina at the head of Smith Cove may have slips open.


Not for navigation. Charts are not updated. 

Going Ashore

If you’re moored at the yacht club, take your dinghy or the club launch in to the floats. In addition to its carefully landscaped grounds, the club has a salt water pool and an appealing dining room. The city of Gloucester seems remote from Eastern Point, but a short walk down any road from the yacht club will take you through some lovely neighborhoods, or out to Eastern Point Light and the Dog Bar.

The harborfront of Gloucester itself has grown increasingly welcoming to visiting sailors in the past few years, with dinghy tie-up available at several convenient spots. The city is proud of its working waterfront, and you’ll not confuse its wharves, warehouses and industrial complexes with other coastal towns that have prettied up for a tourist economy. (In spite of ecological and regulatory travails, Gloucester is the nation’s #13 fishing port by revenue, second in New England to New Bedford.)

Parallel to the waterfront and one block in is Main St., with a dense concentration of restaurants and shops that make for a vital, evolving city. Downtown Gloucester’s variety of eating options close to the harbor, several with truly interesting high-quality menus, would rank it among the top tier of Massachusetts harbors outside of Boston.

The large, granite and gabled house of the artist Fitz Henry Lane sits on a waterfront hill and makes a helpful landmark from in town or on the harbor.

📷 Geoff Rand
Statue of the painter Fitz Henry Lane looks out over the Inner Harbor.
📷 Geoff Rand
Eastern Point Light itself is not open to the public, but you can enjoy the surrounding rocks and Dog Bar breakwater until sunset.

One Hour Ashore

A walk up and round the Fitz Henry Lane house rewards a minimal effort with great views and still leaves time for a stop in town.

Off the Beaten Path

Stage Fort Park is on the northwest corner of the harbor, just across the Blynman Bridge. It’s only about a one mile walk from the downtown waterfront. The Park features beaches, ball fields, picnic tables and grills, a play ground and a seasonal snack bar. The little re-created fort on Stage Head has appropriately commanding views the length of the harbor.

Maritime History

The Essex-built fishing schooner Adventure is undergoing restoration on the Gloucester waterfront.

Rainy Day

The Cape Ann Historical Museum has an impressive collection of Fitz Henry Lane’s work. Their exhibits on the history of Gloucester harbor include boats used by Gloucester natives for early solo crossings of the Atlantic.



The Eastern Point YC mooring fee includes launch service to the clubhouse (not into town). There are dinghy docks at the Town Landing (St. Peter’s, the head of Harbor Cove) and at Salomon Jacob’s Landing (opposite the Anchorage Area, by the Coast Guard and Harbormaster’s buildings).


Brown’s and EPYC have showers for mooring or slip customers. There are public restrooms in the granite Fitz Henry Lane House overlooking the harbor, and in the lobby of the police station at the east end of Main St.

Maps of downtown are posted on old bell buoys near each of the dinghy landings. The harbormaster has a nice welcome kit that includes a map of downtown focused on the typical needs of sailors. There is a visitor center on the waterfront near the western side of downtown.

The Gloucester commuter rail station, at the west end of town, is a modest walk from the waterfront.

Fitting Out

Brown’s, on the south channel of the inner harbor, is the most convenient place to get diesel, water and ice for a sailboat

With much of Gloucester’s commercial activity concentrated near the waterfront, you’ll find most supplies you need a quick walk away from any of the downtown landings. Two small markets, Tedeschi and Truppiano, are at the west edge of town, just past the Blackburn Tavern. There’s a Super Stop and Shop at the east end, a half mile or so from the harbor on the road to Rockport.

A large home center just east of the Fitz Henry Lane house and a nearby auto parts store have helped solve our mechanical problems on several visits.


Brown’s Yacht Yard
VHF: 09 & 19





If you have updated information, corrections, or contributions to this harbor, please share them below. Comments are moderated by Boston Sailing Center. 

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David Filipov
David Filipov
2 years ago

Hey everyone! As of 2021 the harbormaster (very friendly) has incredibly clean facilities. They also have a dock where you can tie up for up to 4 hours. You merely land and sign in on the little clipboard on the dock. It’s very convenient if the crew needs to go to shore to shower or provision. Often empty, even in summer, on weekdays.

David Filipov
David Filipov
Reply to  David Filipov
3 months ago

As of 2023 they were charging $8 an hour for up to 4 hours on that dock. It was honor system, cash only, which means bring exact change if you plan to use it. On the other hand, the dock is more available now that you have to pay for it, and if you’re coming in late or leaving early, the opportunity to stop on shore for an hour or two is still worth it, to me anyway.

Chris Jackson
Chris Jackson
11 months ago

I stayed on a mooring from the Harbormaster through Dockwa. The harbormaster is super friendly and runs a complimentary launch service. They also do pumpouts by boat.

They have 5 mooring locations, I suggest inner harbor. It might be noisy, but it is a very short launch ride.

Take the nearby harbor tour to rocky neck and visit the art galleries and cheese and wine place.


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