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?

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