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The quaint beauty of a Massachusetts seaside town: Rockport, MA

There’s something special about New England. I don’t know if I can put my finger on it, but renting a car and driving through New England (especially in the Fall or Autumn) is quite special. I visited Rockport, Massachusetts on my most recent visit to the region. Even though I lived in Boston for years, I’d never made it up the coast to Rockport. The quaint seaside town sits on the tip of Cape Ann, just a few miles from Gloucester, another quaint New England town.

I’m fairly certain much of the tourism to Rockport and Gloucester is focused on weddings and romantic getaways. And it’s no surprise why! Just look at all the beauty in the details…

Cape Ann, MA

A view from the end of the Rockport city on the tip of Cape Ann

Pass at own risk

Pass at own risk — sign at the end of Cape Ann

live lobster

Lobster—it’s what’s for dinner in Massachusetts :)


Rockport, MA is pretty touristic, but there’s something special about all the quaint gift shops and restaurants

Rockport shop

Gifts shops in Rockport were pretty touristic, but there were still plenty of interesting things to find—from homemade fudge to cheesy t-shirts.

Bear Skin Neck

Historical marker and sign in Rockport

Rockport harbor

Allegedly one of the most photographed harbors in Massachusetts. Very romantic, no?


Fishing boats in the Rockport harbor

Autumn, Rockport

Away from the harbor, there is plenty of autumn sightseeing on Cape Ann

Sidewalk cafe in Rockport

Gloucester’s Main Street is full of even more quaint cafes, gift shops and restaurants—but a bit less touristic than near the Rockport harbor

Gloucester coffee

This café and coffee shop in Gloucester, the Lone Gull Coffee House, has a filing system available for locals who come every day. They can leave their frequent coffee buyer card there rather than having to carry it with them every time.

Gloucester restaurant

The crab cake in this Gloucester restaurant (called Passports) was delicious!

Cape Ann olive oil

What quaint New England town wouldn’t be complete without a shop dedicated entirely to olive oil?

  1. LOVE LOVE LOVE LOVE Rockport!!!! One of my favorite New England towns ever. So glad you got to see it and taste its treats. :)

  2. Great post, you really captured the little details that make small towns special. This place reminds me of the couple days I spent in Maine. I imagine a lot of those coastal areas have the same vibe.

  3. Sofie says:

    Great post, great pics! Make me wanna go:)

  4. Kay says:

    I’ve always wanted to go because I’ve heard it is a cute little seaside town, and I love those. They remind me of movies or storybooks.

    Cool photos and a great post, as always!


  5. Dean says:

    Beautiful seaside town. Looks and sounds lovely…and a bit of a photographer’s dream :)

  6. Andrea says:

    How adorable is this place? I need to explore more of New England

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