The Rudder

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

This cozy, marine-themed gem serves up massive portions of delightful seafood and hearty pasta dishes; don’t forget to bring your own booze!

With sandy shores and calm waters, this cozy beach is the perfect spot for families to soak in sun and views of Gloucester Harbor's lively festivities.

This lively daytime diner serves up generous portions of classic American comfort food, with excellent service and creative drink options that keep patrons coming back.

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

The Beauport Hotel boasts chic, spacious rooms with stunning ocean views, a rooftop pool, and an oceanfront restaurant, all while offering top-notch service and elegant touches.

This beloved Inner Sunset sandwich shop, a local gem since the ’70s, serves up hearty breakfast bites and oversized hoagies, including stellar lobster rolls and a legendary steak and cheese sub.

This family-run brewery and eatery pairs craft ales with delicious pub fare, featuring a scenic waterfront deck for a perfect laid-back hangout.

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

This laid-back waterfront motel boasts cozy rooms with ocean views and easy beach access, serving up free breakfast and a quirky resident parrot for good measure.