The tour starts at the parking lot of the Hammond Castle. You'll hear a story about it, then be guided out of the parking lot for our tour.

Stage Fort Park marks the site where English fishermen established the settlement that eventually became Gloucester. Visitors can enjoy harbor overlooks, historic markers, walking paths, picnic areas, beaches, and some of the best views on the tour.

This historic marker commemorates the 1623 fishing settlement that helped establish the Massachusetts Bay Colony. It provides an important introduction to Gloucester’s early European history and its connection to the Atlantic fishing industry.

The iconic Man at the Wheel statue honors the thousands of Gloucester fishermen who never returned from the sea. Its inscription and harbor setting make it one of the most moving and recognizable memorials in New England.

The Blynman Canal provides a shortcut between Gloucester Harbor and the Annisquam River and is often described as one of the earliest canals dug in North America. Watch boats pass beneath the drawbridge while enjoying views of Gloucester’s historic waterfront.

This small harborfront park honors legendary Gloucester fishing captain Solomon Jacobs, once known as the King of the Mackerel Killers. The park offers waterfront views and easy access to Maritime Gloucester.

Located at the entrance to Gloucester Harbor, Eastern Point Lighthouse has guided ships since the 19th century. The surrounding coastline, harbor entrance, and views toward Dog Bar make it one of the most scenic lighthouse stops on Cape Ann.

Bass Rocks offers dramatic views of waves breaking against Cape Ann’s ancient granite shoreline. The striking light, exposed ledges, and open ocean have attracted artists including Winslow Homer and Edward Hopper.

Good Harbor Beach is one of Gloucester’s most popular beaches, known for soft sand, Atlantic surf, and views toward Salt Island. At low tide, visitors can sometimes walk across the sandbar toward the island.

View the historic Straitsmouth Island Lighthouse from the mainland near Straitsmouth Cove. First established in 1835, the light warns vessels away from dangerous reefs and ledges near Rockport Harbor.

Drive through and explore the historic, artsy must see town of Rockport and hear it's story.

Back Beach offers a rocky shoreline, harbor views, and a clear look toward Rockport’s famous Motif Number One. It is also popular with scuba divers because of its easy shore access.

This red fishing shack is one of the most painted and photographed buildings in America. The current structure is a faithful replica of the original, preserving the symbol that helped define Rockport’s artistic identity.

This historic pier once loaded Cape Ann granite onto schooners bound for Boston, New York, and other East Coast cities. Today, the site offers open-ocean views and a direct connection to Rockport’s industrial past.

The tour ends here at the parking lot.