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Cape Ann, Massachusetts

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By Jason Y. Wood

Rockport, MA

Power & Motoryacht’s Worst-Kept Secrets

Four in Hand

Cruisers venturing along the picturesque shore north of Boston can find a delightful quartet of towns sharing a rocky outcropping.

You may be forgiven if the name of Cape Ann doesn’t immediately ring a bell in the depths of your memory. This is the other cape in Massachusetts, the one located north of Boston that is usually called by its full name, if at all, but most likely you know it from the towns that comprise it. That’s because those towns—Essex, Rockport, Manchester-by-the-Sea, and Gloucester—each offer a different experience for the cruiser.

Manchester-by-the-Sea, with her islands and beaches, seven of each, mind you, offers its own variety, to you and—keep this in mind on weekends—also Boston’s summer escapees. Tie up at Manchester Marine if you want to be right in town. Or drop in on Crocker’s Boat Yard and check out the latest project. Singing Beach, so named for its squeaking sand, draws the largest crowds thanks to its proximity to local public transportation. If you want to take a leisurely stroll around town, you may enjoy a casual lunch at the Beach Street Café or the Landing at 7 Central. Or if the mood takes you, drop in on First Light Anglers right at Manchester Marine and get the lowdown on targeting the area’s striped bass or bluefin tuna.

Rockport dockage is managed by the town harbormaster and because space is limited it’s best to call in advance. An anchorage off Bearskin Neck off Front Beach is handy, but can be an uncomfortable stop if the wind is out of the east or northeast. Here lobstermen and artists live side by side, each seeming to understand the other’s appeal. Nowhere is this more apparent than in the unmistakable red fishing shack on the pier known as Motif No. 1, an oft-photographed and painted edifice that captures the essence of the town as well as the quality of its light.

Rockport, MA

Essex doesn’t recommend itself to cruisers since boat access is somewhat limited to smaller craft up its marshy namesake river, but it’s worth a visit for its most famous invention—the fried clam. Pay a visit to Woodman’s, where this gustatory delight got its start and is available along with steamers, lobsters, and more—try the onion rings. Any wait for a table is mitigated nicely by watching the staff working alfresco to prepare freshly steamed lobster, cutting entry points in claws and tail with large knives, pure entertainment as the shadows grow long in the golden light on the surrounding marsh.

Gloucester, long-storied home of the large commercial fishing fleet, is the most urban of the Cape Ann towns, famous for its memorial statue to local fishermen lost at sea as well as for its role in modern culture as the port hardest hit by what became known as the Perfect Storm, a confluence of weather systems that hit the fleet in October 1991 and was subsequently immortalized in the book and film of the same name. Pay a visit to the Crow’s Nest for a Bud, have a glance at the pictures of George Clooney and Mark Wahlberg already fading, and drink in the culture of a real working, fishing town, as time marches on.