Living Local in Gloucester, MA

To really, truly experience Gloucester, blend some touristy activities with living life like a local. The residents are happy to tell you their favorite place for a lobster roll like their mother used to make or the best beach to find beach glass. But first, you should gain an understanding of the history and the people.

A long, rich history

The Man at the Wheel statue is a memorial to all of the fishermen that have been lost at sea for centuries, up to modern day. Photo courtesy Cape Ann Chamber of Commerce.Gloucester’s history goes all the way back to the early 1600s when French explorer, Samuel de Champlain visited and had peaceful encounters with the Native Americans there. English Captain John Smith visited eight years later. Fishing ruled although agriculture tried to take hold too. Gloucester is one of four communities in the area called Cape Ann (which was so named by England’s King Charles for his mother). The others are Rockport, Essex and Manchester-by-the-Sea. For more details about the area’s history, visit the Cape Ann Museum website

Get to know the people

Because of this rich history, Gloucester residents are incredibly proud, hard-working, compassionate and earnest. The residents are predominantly Italian or Portuguese with active churches and social clubs.

When you ask someone “how’s the fishing industry going for you here in Gloucester?” they are likely to give a sly smile and ask “how much time have you got?” They don’t hold back explaining that they walk a wobbly line between avoiding overfishing and coping with ever-changing government regulations that make keeping their centuries-old way of life, alive.

Then there is the division between those who want Gloucester to stay just as it is and those who have encouraged the building of a large hotel that will begin construction soon. The people on that side of the fence (or should I say “dock”), which include young and old, and fishermen alike, say that without being able to bring in more people, year-round, Gloucester as they know it will die.

 Joey Ciaramitaro, of  Captain Joe & Son’s Wholesale Lobster Company weighs a tub of lobsters just delivered by fishermen. Photo courtesy CDM Communications.Spend a little time at Joey Ciaramitaro’s business, Captain Joe & Son’s Wholesale Lobster Company, which he and his co-owner cousin Frankie have worked at since they were children, and you’ll start to get a real feel for the dilemmas and the passion for Gloucester.  Fishermen in boats of all sizes pull right up to Captain Joe & Son’s dock and greet Joey and Frankie with tubs of lobsters and crab they’ve just hauled up from traps set in the harbor.

After weighing the lobster haul, Joey and Frankie sort the lobsters into tanks to be sold to restaurants, markets and individuals like the Portuguese gentleman who comes in to buy lobsters for dinner, as he has for 30 years. Frankie and Joey work more than 13 hour days, 7 days a week during the lobster season which is approximately May through December. In between the arrival of boats, Joey writes a hugely popular blog for Gloucester residents (and anyone else) that gives snippets of real life in Gloucester. It’s called “Good Morning Gloucester: My View of Life on the Dock” . It’s a great guide to everything Gloucester.

A world ruled by the water

The beautiful ocean off of Cape Ann. Photo courtesy CDM Communications.Beyond understanding the people, a visitor has to grasp what it is to have life revolve around the ocean.  Those who don’t live near a coast can appreciate their mountains, desert, canyons, and lush farmland and feel lucky. But imagine what it must be like to have the massive ocean at your back door, available to you anytime. Want to go for a walk? Okay, walk along the beach, picking up beach glass, seeing surfers and boats. Want to picnic? Sure, take it to the beach but be ready to grab your grub and skedaddle inland as the water rolls in at high tide. Want to go for a drive? You bet. See all the unbelievably charming houses with weathered shingle and wood siding but then don’t be surprised when you round a corner and there’s the ocean with its roaring waves exploding up against the rocks. It’s bigger than life, always changing, always moving and as beautiful as it is dangerous. In a word, it’s “exhilarating” and they are lucky enough to live with that every day. We’re lucky enough to visit and appreciate.

Now that you have a sense for what is so special about Gloucester, you’re ready for your quick lesson in Gloucester Immersion.

When to go: Most people visit Gloucester and the nearby areas during the typical tourist season, Memorial Day through Labor Day. The advantage to that is that all of the seasonal places are open. The disadvantage is that it’s more crowded and harder to get the feel of living like the locals. An ideal time would be before or after summertime when the city collectively exhales and things start to take on a more normal feel. Plus, after Labor Day is the start of “leaf peeping” season. The only down side is that some shops, museums and water tours shut down or reduce their hours. The new hotel may change that though.

Where to stay: There is a variety of lodging around Cape Ann. The primary ones are Bass Rocks Ocean Inn, Atlantis Oceanfront Inn and the Sea Lion Motel plus many B&B’s.

Getting around:  Gloucester has a fine bus system that is dirt cheap and gets you to most everywhere you need. There are also taxis and a commuter rail system serving Boston and points outward. Driving on Cape Ann, like driving in Massachusetts in general can be challenging with narrow, winding roadways and intersections where right-of-way seems only a suggestion. The Gloucester Harbor Water Shuttle and Tour is a smart and fun way to go around the inner harbor, making several stops, getting to see Gloucester from the water side. Get off and on as much as you want for $10. Our captain Peter, and his first mate, young Cole, were entertaining and gave us lots of history, hints and good humor. Be sure to ask about the “lady” who keeps watch up front.


What to do:

·       Get a good feel for Gloucester and a little exercise with the Harbor Walk. See the sights while stopping at granite pillars with informational “postcards” telling about Gloucester’s rich history. Use your smart phone for additional interaction.

·       Do the touristy thing and go on a Whale Watch.  This was an especially good year for seeing the massive creatures up close and personal.

·       Visit one of several excellent museums including the Cape Ann Museum for a history of Gloucester and examples of the many well-known artists who have been so inspired by Gloucester, they made their homes there.

·       Make a day of it at Maritime Gloucester which is part aquarium (including an area where you can touch the sea life) and part maritime history of Gloucester. The latter is brought to you by Gorton’s, the fish stick folks who do, indeed, have their factory in Gloucester.  Their logo is the image of the famous Man-at-the-Wheel sculpture.

·       While you’re there, plan a tour upon the Schooner Ardelle and meet its designer and master shipwright, Harold Burnham. Ask to see the photo album of the making of the Ardelle.  He’ll take you around the Harbor and out to where it meets the sea.  Hold on because it can be a thrilling, bumpy ride on those waves complete with a slap of ocean splashing you in the face. The Ardelle is one of several schooners that make their port on Cape Ann and are available for pleasure trips.

·       Tour the Cape Pond Ice Company made famous by the book and movie “The Perfect Storm” , one of many movies filmed in Gloucester.

·       Visit a historic property like the Hammond Castle, built in the 1920’s, complete with turret, shining armor and even a torture room. Or Beauport Sleeper-McCann House The Beauport Sleeper-McCann House is one of the historic homes available to tour. Photo courtesy CDM Communications., a fascinating look into early American interior design. Built in 1907, it was the summer home of one of America’s first professional interior designers, Henry Davis Sleeper. One of my favorite rooms on the tour was a dining room (one of five) decorated in blue, green and white ocean colors with a long dining table and chairs facing the harbor. The large window dropped down into a wall pocket to enable diners to gaze at and feel the ocean breeze while dining.

Where to shop

The two main roads in the heart of Gloucester are Rogers Street which is a two-way thoroughfare and the one-way Main Street which is where the majority of shops and restaurants are. Curving and undulating, Main Street is conducive to strolling and shopping.  My favorite discoveries are The Bookstore of Gloucester with a cozy collection of good reads; Pop Gallery for artsy gifts; and Toodleoo’s a children’s toy store.  Stop into Beth William’s glass studio on your way to the Cape Ann Museum.  You can buy her beautiful glass jewelry and goodies and watch her at work in her studio.

Scout Vintage Finds is one of the many charming shops in Gloucester. The owner is also a milliner and makes hats using vintage accents. Photo courtesy CDM Communications.Don’t limit your shopping to the main part of Main. Off the beaten path, down East Main are various restaurants and shops including Scout Vintage Finds, a little cottage of a place selling vintage and antique treasures and gorgeous hats for fashion and beach, hand-made by owner/milliner “Scout” King, using vintage accents and trim. See Scout in action too, in her shop-studio.

Where to eat
There’s something for every taste in Gloucester but the locals gave me their list of favorites for casual, social and special dining.


·       Sugar Magnolia’s, aka Sugar Mag’s serves hearty breakfasts and lunch. We loved the light and smooshy Crab Cake Sandwich and Banana bread cake for dessert.

·       Virgilio’s Italian Market, Bakery and Deli serves pastries and huge sandwiches. The subs are enough for two. The Nor’easter and Northender were recommended but the Eggplant Supreme was calling to us. On advice, we took our meal to St. Peter’s Square to enjoy the view of the water and fishing boats and to people watch.


·       Giuseppe’s Ristorante is a loud, happy, and friendly place serving up dueling piano music and hearty Italian dishes like Lobster Ravioli or the spicy Mussels Fra Diavola.  Count on having lots of seafood at many of the fine restaurants in Gloucester. Photo courtesy CDM Communications.

·       Lone Gull Coffee House and Pleasant Street invite meeting up for conversation, board games, going online and to getting coffee and a bite to eat.


·       Alchemy has a dark and exotic feeling, specializing in small plates to share like the truly magnificent morsel - dates stuffed with bleu cheese, wrapped in applewood smoked bacon. Unbelievably good.

·       Passports is known for the warm popovers they bring as a starter. Locals compare notes about how they like to eat them best – before the meal, saved to dip in the juice of mussels or for dessert. We managed to have a little beforehand with butter and the rest to sop up the juices of the chock-full Adriatic Seafood Stew.

·       Duckworth’s Bistrot  is a special treat the locals tell me they go to for anniversaries and other celebrations. Half portions (which are plenty big), make it more affordable. The Ubiquitous Bistrot Salad, New York Strip and Roast Pork were delicious, made even better by the very well-considered wine our jewel of a waitress suggested. She knew her stuff.  The Flourless Chocolate Torte and trademark Banana Cake, well, took the cake, topping off a memorable meal.


Side trips:

Rocky Neck:

No discussion of Gloucester is complete without mentioning its loyalty to art. Every restaurant and most stores display and sell the art of local artists. Many, including some very famous artists such as Winslow Homer and Edward Hopper, have come to Gloucester hearing of the unique light and stay because it’s so wonderful. Rocky Neck is an artist’s colony with one cottage gallery after another with unassuming artists who will gladly chat with you.  The new Rocky Neck Cultural Center provides the artists and those who appreciate them a place to gather, hold art shows and community events.


Although touristy, Rockport is definitely worth a day of your time. The drive from Gloucester to Rockport passes by Surfside Subs a little joint by the side of the road that sells authentic lobster rolls as well as Cape Hedge Beach, a lovely place to eat said lobster roll.

The town of Rockport has one of the most photographed harbors. Photo courtesy CDM Communications.Rockport feels slightly miniature with curved rows of shops decorated with ivy and plump hydrangea bushes. Stop at Roy Moore Lobster Co.  for a snack of smoked salmon or shrimp cocktail or for lobster "in-the-rough" that you can eat on the tiny back deck overhanging the small inner harbor. For coffee or tea, Bean & Leaf has a beautiful view of the ocean.  Stop in Lula’s Pantry which sells kitchen and pantry ware in a chic atmosphere. Grab some crackers, cheese, chocolate and a soda for a picnic because the sea air works up an appetite.

That’s the thing about these areas – everywhere you turn, the ocean and a way of life connected to the sea is right there! It’s amazing, rather magical and to be respected and enjoyed. So eat, shop and play - like the locals.


For more information about Gloucester and surrounding regions, contact the City of Gloucester, MA, the Cape Ann Chamber of Commerce and Good Morning Gloucester.


For a list of all of the movies that have used Gloucester and surrounding areas as film sites, visit:


Courtney Drake-McDonough is a Denver-based travel writer. Her blog offers news and reviews of travel destinations, restaurants, movies, theater and events.

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