The Rudder

Relaxed accommodations, some with decks and kitchens, offering free Wi-Fi & a pool. This relaxed motel with cottages is a 1.5-mile drive from Downtown and 1 mile uphill from Good Harbor Beach. It lies 2 miles from the historic Rocky Neck Art Colony, and 4 miles from the Rockport Golf Club. Motel rooms and suites include free Wi-Fi, cable TV and minifridges. Upgraded units add kitchens and pull-out sofas. Also available are 1- and 2-bedroom cottages with either a deck or a porch. A separate house has 2 suites, 1 featuring a fireplace and stained-glass windows. A heated outdoor pool lined with lounge chairs is available for guest use.

At this rustic gem, chefs elevate New American dishes with global flair, served alongside warm popovers and an inviting art-filled atmosphere.

Nestled on Cape Ann, Gloucester boasts a rich maritime legacy, stunning beaches, and unique attractions like the Hammond Castle and the Cape Ann Museum.

Discover this stunning medieval-style castle built in the 1920s by inventor John Hays Hammond, offering beautiful ocean views and engaging guided tours.

This cozy Gloucester gem serves hearty breakfast and lunch staples like crab cake Benedict and unique pancakes, all in a welcoming, rustic setting.

This charming café serves up a delightful mix of creative and classic breakfast and lunch dishes, making it a must-visit spot for locals and visitors alike.

Seasonal mainstay showcasing local seafood with inventive dishes such as lobster bouillabaisse.

The Cape Ann Museum in Gloucester is a charming haven of maritime history and fine art, showcasing highlights like Edward Hopper's coastal inspirations and diverse collections.

Discover authentic Azorean flavors in a cozy setting where fresh seafood and savory dishes like paella keep diners coming back for more.

Tonno serves up delicious Italian seafood and exquisite old-world wines in a casually chic setting, making it a prime spot for unforgettable dining experiences by the sea.