Gloucester trip planner

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. Gloucester is in Cape Ann. When using our United States trip planner, you're building your holiday based on your own interests, visitor reviews, and the informed opinions of our well-traveled writers.