Type: Outdoor Recreation, Walking / Hiking
Tucked away on a side street in downtown Rockport is a lovely natural area called the Headlands. Sometimes called “the overlook capital of Cape Ann,” it’s just a short walk from Bearskin Neck and a great place to get away from it all.
Starting at Dock Square, walk up Mt. Pleasant Street and turn left onto Atlantic Avenue. At a sharp bend in the road, you’ll see a sign saying “Way to Headlands.” Don’t worry: the trail is flat, short, and not too challenging for kids (or less-outdoorsy types).
In a few minutes, you’ll find yourself ambling over the rugged glacial boulders that give Rockport its name.
The reward for your hike is a rocky outcropping with fantastic views of Rockport Harbor, Sandy Bay, and the northern coastline of Cape Ann. To the south, you can see the lighthouse on Straitsmouth Island. Granite benches placed here and there allow visitors to sit and enjoy a picnic lunch or chat with a companion.
From this spot, the trail continues south for a hundred yards or so, emerging on Old Garden Road. Walk over to Atlantic Avenue and retrace your steps to downtown.