Why you should summer in the laid-back Other Cape of Cape Ann, Massachusetts

GLoucester, Massachusetts is 40 miles north of Boston on the rocky peninsula of Cape Ann, the lesser-known, laid-back cousin of Cape Cod. Gloucester, a busy fishing village and America’s oldest seaport, is celebrating its 400th anniversary^th anniversary of its settlement by English colonists this year. The city’s dramatic coastline features beaches dotted with granite boulders and fishing boats plying the sea and back to the docks, where they dump about 50 million pounds of seafood – including lobster, bluefin tuna, halibut and sea bass – each year.

First settled as a fishing outpost by 14 men from England’s Dorchester Company, later joined by pilgrims from Plymouth Colony, Gloucester eventually attracted Portuguese and Italian fishing families in the 18th century seeking new opportunities. Her influence can still be felt in the city’s Italian and Portuguese restaurants and bakeries, and fresh seafood features heavily on the menu.

Best Beaches

Good Harbor Beach, voted one of the top 25 beaches in the US, is a popular spot with locals looking to cool off from the sweltering summer temperatures of up to 30C, although a dip in the water will remind you that the beaches sit here at the cold north atlantic. At low tide, take a walk on the sandbar to Salt Island, a small rocky outcrop on the shore known as a habitat for wintering and migratory birds and wildlife.

Wingaersheek Beach is situated on the banks of the Annisquam River, which empties into the Atlantic Ocean. The beach is bordered by boulders and has tide pools where you can spot hermit crabs, tiny shrimp, snails and sand dollars. With its long beach and boulders suitable for careful climbing, it’s also a popular spot for hikers.

sailing away

Harsh winters here mean Cape Ann’s summers are focused on the great outdoors. Several tour operators offer whale watching trips from April to October (weather permitting). Stellwagen Bank National Marine Sanctuary, 12 miles off the coast of Gloucester, has been named one of the top five whale watching destinations in the world by the World Wildlife Fund. A variety of whales including humpback, minke and northern right whales, as well as dolphins, porpoises and other marine life come here to feed.

Enjoy an afternoon sailing or sunset cruise on the Thomas E. Lannon schooner, a replica of an early 19th-century fishing schooner. Help raise the sails and enjoy views of Gloucester’s waterfront, working fishing boats, lighthouses and even a medieval-style castle.

American Labor Day weekend in September features the end of summer Schooner Festival celebrating the city’s maritime heritage. Schooners from across the East Coast gather here for a racing competition, tours, parade and citywide block party. A highlight of the weekend is the Parade of Sail, when schooners pull one after another along the city’s waterfront to the Eastern Point Light breakwater, where the Mayor’s race for the Esperanto Cup begins.

boulders and hiking trails

Cape Ann offers miles of hiking trails. Drive to Halibut Point State Park, located on the ocean. On a good day, you can see as far as Maine and New Hampshire from here. The boulders that jut out of the ground here are reminiscent of the history of granite quarrying in the area. It’s also an ideal spot for spotting marine life in tide pools and for bird watching. The now disused quarry has filled with water (although not suitable for swimming). Further down, visit Sea Rocks beach and climb boulders that sit directly on the water.

Between Gloucester and neighboring Rockport lie the ruins of Dogtown, first inhabited by colonial settlers in 1693. Around 100 families lived here at its peak – it was a safe haven away from the coast and marauding pirates and hostile indigenous tribes. Dogtown fell out of favor as a community after the harbors became more used and the risk of danger receded. The last residents were suspected of witchcraft, and some believe that there are supernatural connections today. Dogtown was abandoned in the mid-19th century. All the houses were eventually demolished, but remains of cellar openings can still be found in the ground.

Dogtown is boulder-strewn and best known today for “Babson’s Boulders.” Roger Babson, a 10th-generation Gloucester-based eccentric and millionaire, hired unemployed stonemasons during the Great Depression (much like FDR’s Works Progress Administration project) to go to Dogtown and carve inspirational — and slightly odd — sayings into the boulders . These include “Help Mother”, “Keep from Debt”, “Hole a Job” and “Be Clean”, among others. It is the perfect place for geologists, hikers, walkers and nature lovers.

Step back in time

One of the must-see sights in Gloucester is Beauport, also known as the Sleeper-McCann House. Perched on a bluff overlooking Gloucester Harbor, the whimsical home, a National Historic Landmark, was owned by one of the first professional interior designers in the United States, Henry Davis Sleeper. Each room is decorated in a different color scheme and design theme, often using salvaged materials, and the sumptuous interiors showcase Sleeper’s design talents and obsession with collecting, including folk art, fine china, and amber glassware. The Golden Step Dining Room is a pale green Jazz Age-inspired space with a wall of retractable windows overlooking the harbor, while the Octagon Room, of course, has eight of everything.

Hammond Castle Museum (the same castle you see on a harbor cruise) is a 1920s medieval castle that houses the collections of inventor John Hays Hammond, Jr. Another seafront home with spectacular sea views, houses among its treasures an 8,400-pipe organ, the inventor’s laboratory, and a skull said to belong to a man who sailed with Christopher Columbus.

travel essentials

get there

Jetblue, Delta, American Airlines, British Airways and Virgin Atlantic fly direct from London Heathrow to Boston.

More information

Visit discovergloucester.com