America’s Oldest Seaport - Gloucester, MA

Founded in 1642, Gloucester is a historic coastal city located on Cape Ann in Essex County. It was one of the first English settlements in what would become the Massachusetts Bay Colony. It is known for its old houses, picturesque harbor, vibrant fishing industry, and rich maritime heritage. Today, fishing still remains a vital part of Gloucester's economy and culture.

Here is what caught my eye; I hope you enjoy!

The Gloucester Fisherman looking out over Gloucester Harbor. Leonard F. Craske designed the sculpture, and a small plaque on the base reads, ‘MEMORIAL TO THE GLOUCESTER FISHERMAN, August 23, 1923.’

The Gloucester Fishermen’s Wives Association dedicated a monument to honor the women who have been, and are, the soul of fishing communities.

Gloucester City Hall, built in 1870, was designed by Bryant and Rogers.

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Supreme Roast Beef is a diner manufactured by the Jerry O’Mahony Diner Company of Elizabeth, NJ in 1949. The company manufactured some 2,000 roadside diners from 1917 to 1952.

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Gloucester's beauty has been drawing fishermen, families, artists, and visitors for hundreds of years.

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The Harborview Inn was built in the 1890’s by the Gorton frozen fish family.

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Another view of the Gloucester Fishermen’s Wives Memorial

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Clapboard house with large porch and awnings

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Another view of the Fisherman Memorial

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The oldest part of the Inn at Babson Court was built by Samuel Stevens in about 1750.

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St Anthony’s by the Sea chapel was designed by Edward T. P. Graham and consecrated in 1925.

The Blackburn Building was built in 1900.

Gloucester has a long history as a fishing port, dating back to the early 17th century.

The Last Stop

Rocky Neck is one of the oldest continuously operating artist colonies in the United States.

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Gloucester offers a unique blend of history, natural beauty, and maritime charm on the Massachusetts coast.

Eastern Point Lighthouse was opened in 1833 and automated in 1986.

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Hammond Castle was constructed in the late 1920’s by inventor John Hays Hammond, Jr., known as the Father of Radio Control. 

Beauport, the Sleeper-McCann House, a National Historic Landmark, was the summer home of one of America’s first professional interior designers, Henry Davis Sleeper. Perched on a rock ledge overlooking Gloucester Harbor, Beauport was Sleeper’s retreat, backdrop for entertaining, and professional showcase, and an inspiration to all who visited.

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Annisquam Lighthouse

What you should know:

• You could spend a couple of hours to a couple of days exploring here.

• This is a walkable town.

• On the street parking is available; check posted parking regulations signs.

• Parking may be difficult in season.

• There are many restaurant options.

• Try to visit Beauport and the Hammond Castle while in the area.

For more information: Gloucester MA