Sightseeing Gloucester MA From Your Boat

Barbara Day submits-


Photo caption: America’s Oldest Seaport: Gloucester, MA (courtesy of InAweofGod’sCreation)

With all the history of Gloucester, Massachusetts, there is an endless amount of sightseeing opportunities for visitors to enjoy. It’s a popular destination that you can get to and enjoy by land or water.

The Annisquam River connects Gloucester Harbor with Ipswich Bay where you can dock your boat along the southern end of the river at Cape Ann Marina ( or another Gloucester marina (

Once you’ve arrived, it’s time to enjoy one of America’s oldest seaports and summer travel destinations! Let’s begin our tour…

A glimpse of Gloucester history

●    The area is known as America’s oldest seaport, discovered in 1606 by Samuel de Champlain.
●    At the time, he named the harbor Le Beau Port, meaning beautiful port.
●    The name changed many times before Prince Charles christened it Cape Anne, after his mother. (Now spelled Cape Ann.)
●    In 1623, men from Dorchester England were sent to establish a fishing and trade plantation along the port, the first of any kind in America.
●    They settled the area by setting up fish stages in an area now known as Stage Fort Park.

What to do in Gloucester?

There’s no shortage of activities awaiting you in Gloucester! Ready for some fun on and off the water?

1) Whale watching, fishing & water fun

Whale watching is a popular attraction, 15 miles off the coast of Gloucester. You can also take part in…

●    Fishing charters
●    Kayak tours
●    River cruises

2) Gloucester Maritime Heritage Center

The Gloucester Maritime Heritage Center ( preserves Gloucester’s maritime industrial history. It’s located on the harbor and contains the oldest operating marine railway in the United States. The rail was built in 1849 by Burnham Brothers, Parker, Joseph, and Elias.

A 19th century mill building stands on the Center’s property and holds equipment used to power the railway and a workshop where wooden boats are built. The Center also includes three wharves where you can see fishing vessels from different time periods get a sense for how fishing technology has evolved.

3) Enjoy the water from shore
Find fun in unexpected places in Gloucester, MA!

There are plenty of attractions that allow you to soak in the picturesque waterways from land (or even on the docks!).

●    Beaches
●    Restaurants
●    Museums
●    Parks
●    Art exhibits, including the Rocky Neck Art Colony (, one of the world’s oldest and continuously working art colonies. The Colony has attracted artists and art lovers to the waterfront for over 150 years.
●    Half a dozen lighthouses, dating back to the 1780s

Uncover more info about the fun and excitement that’s ready to be had on the official Gloucester visitor’s website (

4) Gloucester supplies & services

There are several places to get gas and other boating supplies around Gloucester. Here are some of these places for your convenience:

●    Brown’s Yacht Yard, Inc ( – Marinas & Boat Repair – 978-281-3200
●    Cape Ann’s Marina Resort ( – Marinas & Boat Repair – 978-283-2116
●    Cruiseport Gloucester Marine Terminal ( – Port/Launch Services – 978-282-9700
●    East Gloucester Marine – Marinas & Boat Repair – 978-281-0982
●    Gloucester Marine Railways ( – Boat Repairs and Supplies, Port Services – 978-283-2775
●    Rose Marine ( – Marinas & Boat Repair, Boat Supplies, Port Services – 978-283-3334
●    US Coast Guard Station, Gloucester ( – Port Services, Emergencies – 978-283-0705

What’s your favorite Gloucester spot, on water or land?

This article barely scratches the surface of this amazing and unique American treasure. If you live in or have visited Gloucester, please leave a comment with your top list of sights or events or activities!


  • I’ve been in Gloucester for 32+ years – a newcomer! One place to visit for sure would be Main Street in Downtown Gloucester. My gallery (Bodin Historic Photo, 82 Main Street) is on the West End of Main Street, which is very old and historic, and full of interesting shops and eateries: POP Gallery (contemporary), Cape Ann Olive Oil, Cafe Bishco, Virgilio’sItalian bakery (bread of the fishermen), Banana’s vintage clothing (next door to me), Jalapenos Mexican Restaurant (on the other side of me), Premier Imprints, The Cave (hand crafted cheeses, sausage, pate, and great wine at great prices), and Cafe Scilia (coffees, Italian pastries). This is only one block on two sides of Main Street. There’s much, much more – for eating, entertainment, and shopping. Open year ’round.


    • Those are great additions, Fredrik! I used to live there as well for a time…but not as long a time as you! I’ll keep your suggestions in mind when I visit my old stomping grounds again.


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