Sightseeing at Cape Ann

Cape Ann is shaped a bit like a mitten, with the thumb to the right (east); the right half of the mitten is the town of Rockport, the left half Gloucester, which extends onto the mainland past the Annisquam River. For the prettiest back roads, ramble through the left half along the coast, exploring the villages of Annisquam and Lane’s Cove. Don’t miss Halibut State Park at the tip for its sea views and glimpse into granite quarrying history.

But the art galleries, museums, workshops, and theaters are mostly in “downtown” Rockport and Gloucester. Gloucester has more of a working waterfront feel, with a strip of stores on Main Street that includes several good bookshops. A stroll along the waterfront will put you in the mood to explore the fishing schooner Adventure, as well as three terrific museums that showcase both artwork (Winslow Homer painted some of his noted ocean dramas here) and the elegant life of maritime merchants. The Adventure is actually a National Historic Landmark on water, found on the Harbor Loop.

The Cape Ann Historical Museum at 27 Pleasant Street, a block north of Main Street and a block east of City Hall, houses artwork by Winslow Homer, Fitz Hugh Lane, and more, as well as galleries dedicated to maritime life and quarrying, plus historic sailing vessels.

Head into East Gloucester on Route 127A to reach Beauport, the Sleeper-McCann House, which is a 45-room mansion housing collections of artwork, porcelain, and Chippendale furniture. While you’re out on the eastern point, go to the end of the road and visit the Dog Bar Breakwater and Eastern Point Lighthouse, where the US Coast Guard offers daily summer tours.

On your way back to town, stop to visit Rocky Neck Art Colony, where for 150 years artists have set up their easels, sculpting studios, and more. Visit the galleries (a couple of these are open year-round, but most are warm-weather sites), as well as the restaurants, or just sit on the shore of Smith Cove and savor it. There’s plenty of parking.

History buffs will appreciate the Sargent House Museum at 49 Middle Street, built in 1782 for writer and activist Judith Sargent Murray, one of the first Americans to champion women’s equality, education, and economic independence. Her husband, the Rev. John Murray, was the founder of Universalism in America. Period 1790 furnishings include glass, silver, textiles, portraits, and personal items ranging from shaving stands to bed warmers.

Sightseeing in Rockport

The heart of Rockport is at Rockport Harbor, around the north side of the mitten “thumb.” Here are the Sandy Bay Historical Society and Museum (40 King Street), and the Rockport Art Association, as well as “Motif #1,” a bit of a local joke – the red fish shed at the end of Tuna Wharf, said to be one of the most painted parts of Cape Ann (we’re talking paintings here, not the shed walls). Head north of Rockport on Route 127 to Curtis Street and turn onto Pigeon Hill Street following the signs for the Paper House, an extraordinary construction actually made of newspapers – about 100,000 copies, to make the house and the furniture. When you’re finished admiring such ingenuity, backtrack to the coast and enjoy the peace and beauty of the village of Pigeon Cove.