Annisquam and Wingaersheek Beach, Massachusetts

This Massachusetts waterway is a hive of activity and excitement.

Annisquam and Wingaersheek Beach, Massachusetts


Just inside the entrance to the Annisquam river on Massachusetts’ North Shore is the harbor of the same name. On the eastern side of the river is the Annisquam Yacht Club, an active and hospitable sailing club that’s always a hive of activity during summer months. On the opposite side of the river is Wingaersheek Beach. My wife and I agree that it’s so beautiful, with its turquoise water and white sand, that it looks almost tropical and out of place in Massachusetts. As you hang on your mooring— the yacht club maintains several for visitors—you feel as though you’re bobbing in a cove in Bermuda.

Since the Annisquam River is the inside, well-protected route across Cape Ann to Gloucester, it’s a busy waterway. There, you’ll have the pleasure of viewing a wide variety of watercraft—everything from vintage wooden sailing dinghies to cigarette boats. Whenever we sail out of our home port of Newburyport, Massachusetts, bound for southern harbors, we have to decide whether to head east around Cape Ann or go down the Annisquam. Both routes have their own charms. But unless the wind is a strong easterly, we usually choose to spend some time bobbing in the “little slice of Bermuda.”

Glenn Dill is from Plymouth, Massachusetts.