Wingaersheek Beach

The Annisquam River is a tidal, salt-water estuary in the Annisquam neighborhood of Gloucester, Massachusetts, connecting Annisquam Harbor on the north to Gloucester Harbor on the south. The segment between Gloucester Harbor and the Newburyport/Rockport Line bridge is also known as the Blynman Canal. The estuary is about 4.5 miles (7.2 km) long, navigable, and open to the ocean at both ends. Its surface area is 1.9 square miles (4.9 km2). The name "Annisquam" comes from an Algonquian term meaning "top of the rock, containing , "on top of", and <-ompsk>, "rock". The first European settlement in Annisquam was established in 1631. The river was dredged by the United States Army Corps of Engineers in 1965 to create a channel some 8 feet (2.4 m) deep, and 60 to 200 feet (18 to 61 m) wide. Annisquam Harbor Light stands on the east, Cape Ann, side of the north entrance to the river. There are only three fixed crossings of the river: Massachusetts Route 128, the Rockport Branch of the MBTA Newburyport/Rockport Line, and Western Avenue (Massachusetts Route 127). There are strong tidal currents in the river, and unusually the current flows in opposite directions at the two ends.

The Edward Harraden House is a historic house in Gloucester, Massachusetts. It was built on land purchased by Edward Harraden in 1656, who is presumed to have built the house not long afterward. It was one of the early houses in the development of Annisquam village. It is a 2+1⁄2-story seven-bay colonial with an off-center central chimney. The oldest portion of the house is the second through fourth bays from the left; the interior sections to the right of the chimney was added sometime before 1765. The house was afterward further extended by one bay on each side. The only clear evidence of its First Period origins is in the attic, or is covered over by the walls.The house was built c. 1660 and added to the National Register of Historic Places in 1990.

The Dyke-Wheeler House is a historic colonial house in Gloucester, Massachusetts. The 2+1⁄2-story plank-framed First Period house was built in about 1720, and has a typical center chimney plan. The leanto section was added c. 1800. The house was at one time believed to have been built earlier, in the 1660s, by a man named Richard Dyke. The house was later owned by the Wheeler family for whom Wheeler's Point, where the house is located, is named. It is one of two First Period houses surviving on Wheeler's Point.The house was listed on the National Register of Historic Places in 1990.

The Annisquam Bridge is a historic bridge in Annisquam, Massachusetts, a village within the city of Gloucester. The bridge was built in 1861 to replace an earlier 1847 bridge that crossed Lobster Cove. It is a wooden pile bridge, a type of which only two others were found in New England as part of a c. 1979 survey. The bridge is 440 feet (130 m) long and 30 feet (9.1 m) wide, and had a drawbridge section in the center that was moved by a hand-cranked winch. The bridge has repeatedly been the subject of safety closings and restorative work over the course of the 20th century, and was completely rebuilt in 1946–7, removing the draw. Despite this, it was closed to vehicular traffic in 1968, and pedestrian traffic in 1987. The bridge has since been rehabilitated, and is open to pedestrian traffic. The bridge was listed on the National Register of Historic Places in 1983.

The Norwood-Hyatt House is a historic house at 704 Washington Street in the Gloucester, Massachusetts. It is notable as one of the oldest houses in Gloucester, and for its association with Alpheus Hyatt, who did research in marine biology here before establishing the Marine Biological Laboratory at Woods Hole. The oldest part of the house is estimated to have been built in 1664 for Francis Norwood, a mariner and early settler of Gloucester. It remained in the hands of Norwood family descendants until 1879, when Cape Ann Bank took the house by foreclosure. It was acquired that year by Audella Hyatt, wife of Alpheus Hyatt. In 1880 Hyatt used the property as a base for marine research, but abandoned that use, finding it unsuitable, after one season. It was owned by descendants of the Hyatts until 1987.The construction history of the house has not been researched in detail. It is a 2.5-story wood-frame structure, with its earliest framing members showing evidence of 17th century construction methods. It was repeatedly expanded, particularly during the Norwood family's ownership, to reach its present configuration. The main block of the house is five window bays wide, and there is a two-story ell added on to the west side (probably in the early 19th century), and several shed-style additions on the northwest part of the house. The foundation is mainly mortared stone, but the eastern wall is made of brick.The interior of the house has significant features that remain from the 17th and 18th centuries. Many original fireplaces and mantels survive, although most of the fireplaces have been covered over. There are wide pine floors, and the walls and woodwork show many examples of 18th and 19th century construction techniques. Many of the walls were painted with artwork, largely by Audella Hyatt.The house was listed on the National Register of Historic Places in 2000.

Annisquam is a waterfront village in the city of Gloucester, on the North Shore of Massachusetts. It is a few miles across Cape Ann from downtown Gloucester.

Annisquam Harbor Light Station is a historic lighthouse on Wigwam Point in the Annisquam neighborhood of Gloucester, Massachusetts. It can be viewed from nearby Wingaersheek Beach, Gloucester. It lies on the Annisquam River and is one of the four oldest lighthouses to surround the Gloucester peninsula as well as; Eastern Point Light, Ten Pound Island Light, and Thacher Island Light.

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.

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 Sargent-Robinson House is a historic house in Gloucester, Massachusetts. Built about 1760, it is a well-preserved example of an iconic local form, the gambrel-roofed cottage. It also includes probable foundational remnants of the c. 1700 house built on the site, and was owned into the 20th century by descendants of Samuel Sargent, who settled the land in 1695. It was listed on the National Register of Historic Places in 2016.

Dogtown (also Dogtown Commons or Dogtown Common or Dogtown Village) is an abandoned inland village in Gloucester on Cape Ann in Massachusetts.

Harbor was an MBTA Commuter Rail station in Gloucester, Massachusetts. It served the Rockport Branch of the Newburyport/Rockport Line. A short-lived stop, it was open from 1977 to 1985.