Guide To Rockport, Massachusetts

Coastal charm, leisurely pace and history define the region of Northshore in Massachusetts and Rockport is no exception to that. Coastal New England has me longing for a time decades ago that I never knew.

We stayed in Swampscott, MA this summer but coastal New England is such a driveable area it makes day trips easy and jam-packed with scenic views. The drive from Swampscott to Rockport is a quick 45-minute drive. You can also take a commuter train from Boston to Rockport that will get you there in about 75 minutes. Rockport is a town of about 7,000 residents just 40 miles north of Boston in the Northshore region. Rockport is situated on the tip of the Cape Ann peninsula, an area that is also home to famous seaside towns like Gloucester and Manchester-by-the-Sea.


The most famous aspect of Rockport is Motif No. 1. It is considered the most painted building or structure in the United States. The shack is a favorite amongst artists because of the composition and lighting of its location. It was built in the mid-1840s to house fishermen's supplies and daily catches. When the U.S. Naval Fleet docked in Rockport, it then became a place for meeting and watching ship launches. In the 1930s, it became an artist’s studio before finally serving as a city-owned monument to the area’s veterans. Rockport quickly gained notoriety as an artists’ haven & painters flocked to the area. Lester Hornby loved the area and taught painting classes in the summer. He sent students to paint whatever scenes caught their eyes. He saw a trend in the work. His students favored the small red fishing structure over anything else on Rockport’s seaside landscape. It was the quintessential icon of a New England fishing town. It was becoming a “motif” — a french term for a theme within a work of art that often repeats itself. There is a local legend that says once being presented with another rendition of the shack, Hornby exclaimed “What? Motif No. 1 again!” hence the name & notoriety came to be.

You can spot the shack from many overlooks across the harbor, or you can walk alongside it or on the dock across from it, as we did, by exploring the alleys off of Bearskin Neck.


When you get to Rockport, you are immediately presented with gorgeous architecture taking you back to a previous time. It is a quaint and beautiful coastal town full of history. Taking in the architecture, gazing out at the sailboats dotting the water or popping into the various shops and restaurants makes for a pretty serene day. The shops offer a wide variety of eclectic, unique, and often locally-owned. As you stroll down Bearskin Neck, you'll be at the very tip of the peninsula that stretches out to surround the harbor. It’s lined with quaint shops, art galleries, and restaurants (plus an unusual number of ice cream shops). It provides excellent people watching - one of my favorite hobbies.


My favorite stops include: - Roy Moore Lobster Co. We didn't get to stop here and eat as we made plans to eat elsewhere but it is a

constant recommendation from everyone who has been here. They had a long line

and the food looked incredible and smelled even better. It would be perfect to grab

a little snack here to taste as you walk up and down the alleyways. - The Fudgery As you can imagine, the sweets are to die for. The fudge is a must. My preference is

the classic.

- Cape Ann Coffees I am an avid coffee drinker. I tend to drink my coffee black or I get a dirty chai with a

milk alternative. Their dirty chai was perfect. Not too sweet, just the right amount of

spice and espresso.

- 7th Wave The New England steamers are a MUST, as is the clam chowder. I think we devoured

it in minutes. I also had the lobster. As with any lobster in New England, it is like

heaven in your mouth - soft, buttery goodness. The bartender also made us a

specialty drink. I believe it was like a pomegranate margarita or something but it

was super tasty. The staff, especially the lady managing and running, were

absolutely fantastic, helpful and welcoming.


- Susie's Stories If you know me, you know I love reading but even more importantly, you know one

of my favorite places in the world is a bookstore. I could spend hours perusing book

stores, ideally with a cup of coffee in hand. Susie's Stories is the most charming little

bookstore I've seen.


- Strut Boutique I love boutiques and Strut did not disappoint. They have an assortment of classic

and trendy, high-quality items. Their staff is extremely friendly and accommodating.

It is a very small space so it can get crowded easily. I found a fantastic pair of pants

and my girlfriend found a few things as well.


Rockport, Mass is definitely an area you should explore if you make your way to the Northshore. Let me know if you go and what your favorite things were.

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