Cape Ann Itinerary

Ipswich has more First Period, or circa-1626 to circa-1725, homes than any other town in the country. Don’t miss the new pedestrian Riverwalk that connects parts of downtown to the Ipswich River. Along the Riverwalk is a 1,700-square-foot “History of Ipswich” mural where the faces of present-day townspeople appear in scenes depicting local history and famous residents, including artist Arthur Wesley Dow and poet Anne Bradstreet. Minutes down the road, you’ll find the Great House of the grand 1928 summer estate at Castle Hill open for tours as well as the adjacent Crane Beach, owned by the Trustees of the Reservations.

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Massachusetts’ “other” Cape is a well-kept secret. For a relaxing day of sandy beaches, harbor walls, lighthouses, and lobsters-without sitting in hours of traffic-this portion of the North of Boston region is just what the doctor ordered.

Cape Ann includes the following communities: Gloucester, Essex, Ipswich, Manchester-by-the-Sea, and Rockport, the central portion of the Essex Coastal Scenic Byway. Each has its own flavor, texture, and, of course, colorful characters to discover. Staying in any of these four towns and traveling to another to sight-see or dine is simple, so don’t hesitate to go where your curiosity leads you.

In Essex, stop for fried clams where they were invented, at Woodman’s of Essex. Located right on Main Street, this New England institution is within walking distance of the famous Essex Shipbuilding Museum and more than 20 antique shops. Essex is said to have the most antique shops per square mile of anywhere in the country.  Cruise along the Essex River, enjoying its unspoiled natural beauty, with Essex River Cruises and Charters.

Just a few miles east on route 128, you’ll enter Gloucester, America’s oldest seaport. Here you’re greeted by iconic statue of “The Man at the Wheel,” commissioned in memory of the thousands of fishermen lost at sea.

Its companion, “The Fishermen’s Wives” memorial, steps away from the historic Stage Fort Park welcoming center. See the evolution of fishing vessels on Harbor Loop where the Heritage Center sits. Other parks to visit include Dogtown, the long-gone site of a 1700s farming community donated to the city by local businessman Roger Babson. Babson had boulders throughout the wooded trails inscribed with inspirational words like “Courage” and “Industry.”

Any visit to Gloucester should include time on the water and there are plenty of options to enjoy!

Two choices for harbor tours are the Schooner Thomas E. Lannon and the Schooner Ardelle, which elegantly glide through Gloucester Harbor within easy viewing distance of the quintessential New England lighthouses that dot the harbor. Whale watching, a favorite activity of visitors and locals, is at its best in Gloucester, the closest point in Massachusetts to the whale feeding grounds of Stellwagen Bank and Jeffrey’s Ledge. Whale watching companies operate from May to October and many also offer full- and half-day deep sea fishing trips. Departing from Gloucester are Cape Ann Whale Watch and 7 Seas Whale Watching.

Nearby Rockport is also an artistic hub – with its quaint downtown and famous “Motif #1” fishing shack off the main pier, it’s easy to see what has inspired more than 150 years worth of visitors-among them Fitz Henry Lane, Winslow Homer, Edward Hopper, Childe Hassam, and John Sloan-to pick up a paintbrush and make Rockport a part of their lives. After browsing the shops at Bearskin Neck, take in true Cape Ann views at Halibut Point State Park. This former seaside quarry and lighthouse is now surrounded by walking trails that lead to an outcropping of boulders along crashing waves. Even in winter the views are remarkable-just watch your step!

Expect to find only the freshest seafood, often caught that very day, anywhere you stop to eat on Cape Ann. Visit the Seaport Grille or 1606 Restaurant, both operated by the beautiful seaside Beauport Hotel. Manchester-by-the-Sea boasts Singing Beach (the sand really does make a distinctive squeak when you walk on it).

Photo credit: Rod Parker

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