Whittemore House (Gloucester, Massachusetts)

The First Parish Burial Ground is a historic cemetery located at 122 Centennial Avenue in Gloucester, Massachusetts. Established in 1644, the 2.5 acres (1.0 ha) site is Gloucester's oldest burying ground. It once stood at the heart of the Gloucester settlement, and was for 80 years its only cemetery. It was listed on the National Register of Historic Places in 1975. It is now being maintained jointly by the city and the Cemetery Restoration Partnership.

The Oak Grove Cemetery is a historic cemetery, founded in 1854, which is bounded by Derby, Washington, and Grove Sts., and Maplewood Avenue in Gloucester, Massachusetts, United States. The cemetery was founded by a group of local businessmen who sought to establish a cemetery in the then-fashionable rural cemetery style. They hired landscape architects Robert Morris Copeland and Horace William Shaler Cleveland to lay out a series of winding lanes. The Bradford Chapel was built through a bequest by George R. Bradford, another local businessman, and built in 1903–04. The cemetery is still privately owned, and has grown over time to occupy 11 acres (4.5 ha).It is the burial place of the operatic soprano Emma Abbott.The cemetery was listed on the National Register of Historic Places in 1975.

The Babson-Alling House is a historic colonial house in Gloucester, Massachusetts. The 2.5-story Georgian house was built in 1740 by William Allen, and remains one of Gloucester's finest houses of the period. It is a typical house of the time, with a center chimney plan and a gambrel roof. The house was bought by Joseph Low in 1779; his daughter Elizabeth married Nathaniel Babson, and their son ended up inheriting the property. It remained in the Babson family into the 20th century, eventually being inherited by Low descendant Elizabeth Alling.The house was listed on the National Register of Historic Places in 1996.

The White–Ellery House is a historic house located at 247 Washington Street in Gloucester, Massachusetts. It is on the National Register of Historic Places. It is owned and operated by the Cape Ann Museum, whose headquarters is located at 27 Pleasant Street in Gloucester.

Gloucester High School ( GLOST-ər) is a public four-year comprehensive secondary school, with 865 students and 150 faculty and staff, serving Gloucester, Massachusetts. It is accredited by the New England Association of Schools and Colleges and is a member of the Northeast Alliance of High Schools.

The Gloucester Net and Twine Company is a historic factory in Gloucester, Massachusetts. It was the factory of one of Gloucester's most importing fishing-related manufacturing businesses, founded in 1884. The complex was built c. 1899. The main factory building is a utilitarian wood-frame structure three stories high, six window bays wide and fourteen long. Its long facade, along Maplewood Avenue, is centered on a four-story tower, to the right of which is a single-story brick power supply building with Italianate detailing.The complex was listed on the National Register of Historic Places in 1996.

Gloucester station is an MBTA Commuter Rail station in Gloucester, Massachusetts. Located off Railroad Avenue and Washington Street in downtown Gloucester, it serves the Rockport branch of the Newburyport/Rockport Line. The station consists of a single side platform serving the line's single track. The station has a mini-high platform, making it accessible.

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.

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. Later owners also operated it as a hotel space, including one who gave it the name "Puritan House". It now houses other businesses.The building was listed on the National Register of Historic Places in 1976, and was included in the Central Gloucester Historic District in 1982.

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. It was added to the National Register of Historic Places in 1982.

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. A hat maker operated on the ground floor, and apartments were above. 65–67 Main Street, a three-story four wide block with Federalist styling, was built for Samuel Bulkley. A "tin manufactory" operated on the ground floor, and there were apartments above. This building shared a wall with 69–71. 61–63 Main Street, also three stories and four wide, was built for William Babson, Jr., and had a shop on the ground floor with apartments above. In 1890 this building was renovated, giving it a new Victorian facade, and an enlarging addition to the rear. 55–59 Main Street is distinct from the other three buildings in being only two stories, and for having a hipped roof. It was built for Henry Smith, and first housed a cabinet maker on the ground floor, with living space above.They were collectively listed as a historic district on the National Register of Historic Places in 1974, and further included in the Central Gloucester Historic District in 1982.

Short & Main is a restaurant in Gloucester, Massachusetts. It was included in The New York Times's 2024 list of the 22 best pizzerias in the U.S.