Downtown + Boulevard

Cape Ann Museum is an art and historical museum located in Gloucester, Massachusetts. Its collection and programming focuses on the artists and art colonies of Cape Ann, including the Rocky Neck Art Colony and the Folly Cove Designers. The museum's collection also features objects from Gloucester's fishing and maritime history, and granite quarrying history.

The Folly Cove Designers were a mid-20th-century group of American artists block printing in Gloucester, Massachusetts, on Cape Ann. Their blocks were made of linoleum, and they primarily printed on fabric.

The Fitz Henry Lane House is a historic house at 8 Harbor Loop Road, on the harbor side of Rogers Street in Gloucester, Massachusetts. The three-story stone Gothic Revival building was designed and built in 1849 by the artist Fitz Henry Lane, and was his home until his death in 1865. The building now sits in a municipal park, and has a commanding view of the harbor.

The Central Gloucester Historic District encompasses the historic commercial, civic, and residential core of the fishing community of Gloucester, Massachusetts. Now largely defined by 19th century architectural trends, it includes the city's commercial downtown (Main Street), its civic heart on Dale and Prospect Streets, and some adjacent residential areas.

Fort Defiance was a fort that existed from 1794 to after 1865 on Fort Point in Gloucester, Massachusetts. The location protecting the inner harbor was also called Watch House Point.

The Front Street Block is a series of four connected commercial blocks in the West End of Gloucester, Massachusetts, USA. They were built in 1831 after a fire had devastated Gloucester's downtown the previous year.69–71 Main Street, a three-story four wide block with Federalist styling, was built for Aaron Day.

Gloucester Fisherman's Memorial (also known as: "Man at the Wheel" statue or "Fishermen's Memorial Cenotaph") is a historic memorial cenotaph sculpture on South Stacy Boulevard, near entrance of Stacy Esplanade in Gloucester, Massachusetts, built in 1925.

Stage Fort Park is a park at Stage Head in Gloucester, Massachusetts, part of the Essex National Heritage Area. It contains two beaches, a large playground, picnic benches, two baseball fields, a basketball court, a dog park and plenty of room for any weekend activities. The park includes Gloucester's Visitor and Welcome Center and Stage Fort, a reconstructed Civil War fort on a site fortified since 1635.

The Sargent House Museum is a historic house museum located at 49 Middle Street, Gloucester, Massachusetts. The museum is open on weekends from Memorial day to Columbus day, and offers guided tours of the historic home, a small gift shop, and rotating exhibits in its exhibit space.The Sargent House was built in 1782 for the feminist writer and philosopher Judith Sargent Murray and her first husband, John Stevens, a merchant in the West Indies trade.

The Puritan House is a historic hotel building at 3 Washington Street and 2 Main Street in Gloucester, Massachusetts. It was the first brick building to be built in the city. It was built in 1810 form James Tappan, a schoolteacher from New Hampshire who once had Daniel Webster as a student. Tappan operated Tappan's Hotel on the premises, and it served as a major social center for the community.