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Rockport and Gloucester 2 Day Itinerary

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Fishing Boat on Gloucester Harbor | Rockport and Gloucester MA 2 day Itinerary
Fishing Boat on Gloucester Harbor

There is much to do in the coastal New England towns of Rockport and Gloucester MA. The neighboring communities are teeming with fishing wharves, galleries, and beaches. In Rockport, you will find a village full of artists and crafters. In Gloucester, a community of fishermen will impress you with their devotion to the sea. Our Rockport and Gloucester MA 2-day itinerary (with map) will you help fit in all the fun.

Lunch on the Water | Rockport and Gloucester MA itinerary | New England travel blog
Lunch on the Water

A unique quality to the area is how close you can get to its fishing and arts communities. Walking the wharves you can meet local lobstermen, chat with the fishermen from Nat Geo's Wicked Tuna, and/or meet the artist who created the watercolor you are thinking about purchasing. The region is beautiful, walkable, and accessible.

Jodrey State Fish Pier | Gloucester Harbor | New England Travel Blog
Jodrey State Fish Pier

In our article it is not Rockport vs Gloucester. We love both Massachusetts communities and we hope you enjoy our Rockport and Gloucester MA itinerary. Like much of New England, the area is best seen by private vehicles. Click here to check out rental car pricing.


This 2 day itinerary includes an overnight stay. Click here for information on Rockport MA hotels and Gloucester MA hotels.. TIP: In Rockport we like the retro Bearskin Neck Motor Lodge; and in Gloucester, we like the the Hotel at Cape Ann Marina.

Rockport and Gloucester MA 2 Day Itinerary with Map At A Glance