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Trip Planner USA  /  Massachusetts  /  Cape Ann  /  Gloucester

Gloucester

4.3
Dolphin & Whale Watching · Beaches · Monuments

Sandy Bay

The still waters off the Gloucester shore are immortalized in paintings and prints produced by the hundreds of artists who visit this town. This rich culture has a foundation that reaches back to pre-revolutionary settlement. Some of the architecture of this period sits perched atop one large hill that overlooks the town, while a few houses down the hill in the city center are preserved from the 18th and 19th centuries. These wooden structures sport red and white paint and house cozy restaurants and shops. Many of these sell food and items that reflect the rich fishing culture that the town is known for. Take a look at our United States sightseeing planner to refine the details of your trip to Gloucester.
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Popular things to do in Gloucester

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4.7
Duration: 4 hours
4.8
Duration: 2 hours
4.8
Duration: 2 hours
4.6
Duration: 2 hours

Side trips from Gloucester

4.9
Duration: 2 hours
4.5
Duration: 2h 30 min
4.5
Duration: 1h 30 min
2.3
Duration: 1 hour

Hidden gems in Gloucester

5.0
Duration: 2h 30 min
4.4
Duration: 2 hours
4.9
Duration: 2 hours
5.0
Duration: 2 hours

Beaches in Gloucester

4.8
Duration: 2 hours
4.4
Duration: 2 hours
4.5
Duration: 2 hours
4.1
Duration: 2 hours

Museums in Gloucester

4.7
Duration: 1h 30 min
4.8
Duration: 2 hours
4.4
Duration: 2h 30 min
4.1
Duration: 2 hours

Kid-friendly things to do in Gloucester

4.0
Duration: 2 hours

Where to stay in Gloucester

The town prides itself on maintaining a quaint New England charm. Many inns and rental properties offer views, or accommodation in historical red-brick buildings. Some accommodations have only a few rooms, so book ahead to ensure you get the room of your choice.
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