Hidden annisquam: a walking tour through a charming Cape Ann village

One of the pleasures of visiting Boston’s North Shore is taking short walks that reveal a small village’s charms

Annisquam is a charming village on the North Shore of Boston, off the beaten track in Gloucester. Many North Shore visitors drive by on meandering route 127, unaware of its quaint charm. A walking tour of Annisquam Village in Gloucester Massachusetts gives you the perfect opportunity to explore its unique character. It sits at the mouth of the Annisquam River, and it’s winding streets are lightly trafficked, providing a safe place to walk through the picturesque village.

Where to start your walk

We suggest parking next to the lovely Annisquam Village Church at the entrance to the village, just off of Route 127. Walking towards the village on Leonard Street, let’s take a slight detour through a residential neighborhood, and return to the main street and walk through the village.

Enjoy the center with its charming Village Hall, the center of summer activities. Stroll down to the Bridgewater Street pedestrian bridge and walk out to take in Annisquam Harbor with its pleasure and working boats. Returning to shore, you’ll pass by the Talise, sitting on a pier and offering some of the finest seafood on Cape Ann. To dine on their deck overlooking Lobster Cove is an unforgettable experience. They are open May through October. Be sure to make reservations well in advance!

Continue past the Annisquam Yacht Club, perched on pilings at the mouth of the Annisquam River, and gaze across the water at Wingaersheek Beach to the south. Follow the map past huge Squad Rock, a glacial erratic, to Squam Rock Pasture. You’re now facing west, looking down the length of Wingaersheek, and to the north enjoy the view of the tiny lighthouse at Annisquam Harbor Light Station.

We’ll conclude our walking tour of Annisquam Village by retracing our steps back to the car on Leonard Street. We’ve taken in some of the best views on Boston’s North Shore on a short stroll.