Chequesset Inn

The First Congregational Parish Historic District encompasses the oldest church building in Truro, Massachusetts and adjacent historic resources. The congregation was established in 1711, and is now occupying its third church, a Federal/Greek Revival building erected in 1827. The tower houses a bell cast by Paul Revere. Adjacent to the church and part of its setting is the Congregational Cemetery, whose earliest recorded burial is in 1810, and has been associated with the church since its construction. The cemetery contains a memorial erected in 1841, commemorating the loss of 57 Truro residents and seven ships in a gale on October 3. 1841.The district was listed on the National Register of Historic Places in 2013.

The Mayo Beach Light was an early lighthouse on Cape Cod. Deactivated in 1922, the second tower was moved to California and re-erected as the Point Montara Light in 1928.

Wellfleet is a town in Barnstable County, Massachusetts, United States, and is located halfway between the "tip" and "elbow" of Cape Cod. The town had a population of 3,566 at the 2020 census, which swells nearly sixfold during the summer. A total of 70% of the town's land area is under protection, and nearly half of it is part of the Cape Cod National Seashore. Wellfleet is famous for its oysters, which are celebrated in the annual October Wellfleet OysterFest.

Herring River is a river in Wellfleet, Massachusetts that includes a tidal estuary. As of 2014, there are plans and funding in place to restore the river, after the construction of a dike across the river in 1909 as a mosquito control project severely hampered the health of the estuary.

Wellfleet station was a train station located just to the east of the intersection of Commercial Street and Railroad Avenue in Wellfleet, Massachusetts. It was constructed in 1870 when the Cape Cod Railroad reached Wellfleet.

The Samuel Smith Tavern Site is a historic archeological site in Wellfleet, Massachusetts. It encompasses the remains of a late 17th-century tavern operated by Samuel Smith, owner of Great Island, which shelters Wellfleet Harbor. The tavern site is located within the Cape Cod National Seashore, and is accessible via the Great Island Trail. The site was excavated in 1969–70, recovering thousands of artifacts, including clay pipes, drinking artifacts, a harpoon, and a chopping block fashioned from whale vertebrae.The tavern site was listed on the National Register of Historic Places in 1977.

The Wellfleet Center Historic District is a historic district in Wellfleet, Massachusetts. It encompasses resources that exemplify the development of the community, beginning in the late 18th century, as a thriving commercial maritime center, and then its rise as a summer resort community in the late 19th century. Buildings in the district include Cape-style houses from the mid-18th century, 19th century commercial and institutional buildings in the town center, and the 1880s summer estate of Lorenzo Dow Baker. The district is roughly bounded by Cross St., Holbrook Ave., Main, E. Main and School Streets, and Duck Creek, and was listed on the National Register of Historic Places in 1989.

The Ahearn House and Summer House are a pair of houses at 450 Pamet Point Road in Wellfleet, Massachusetts. The smaller "summer house" is an early 19th-century cottage, while the main house is a subsequent construction; both are important examples of period architecture in the community. The property was listed on the National Register of Historic Places in 1984.

The Atwood–Higgins Historic District encompasses a historic property with deep colonial roots in Cape Cod National Seashore. Located on Bound Brook Island on the west side of Wellfleet, Massachusetts, the centerpiece of the district is the Thomas Atwood House, built c. 1730. The property is emblematic of Cape Cod's colonial origins and its later transformation into a summer resort area. The house was listed on the National Register of Historic Places in 1976; the district was listed in 2010. The property is open for guided tours by the National Park Service on a seasonal basis.

The Townsend House is a historic house at 290 Paine Hollow Road in Wellfleet, Massachusetts. The 1+1⁄2-story full Cape style wood-frame house was built in 1804, probably by Doctor James Townsend, whose descendants owned the house well into the 20th century. The most notable resident was Samuel Campbell, an English engineer who worked with Guglielmo Marconi on the transatlantic wireless facilities in Wellfleet. The house is notable as a particularly little-altered example of the style, with details typically only found in houses of wealthier owners. The house was listed on the National Register of Historic Places in 1998.

The Saunders–Paine House is a historic house at 260 Paine Hollow Road in Wellfleet, Massachusetts. This 1+1⁄2-story Federal style Cape was built c. 1830, and is a well-preserved local example of the style. The first known owner was Charles Saunders who married Mary Cole Paine, whose family gave the area its name. The house was listed on the National Register of Historic Places in 1998.

The Paine Hollow Road South Historic District is a residential historic district roughly along Paine Hollow Road, and Raywid Way in Wellfleet, Massachusetts. It consists of a cluster of seven 19th-century residences centered just north of Paine Hollow Road's junction with Pleasant Point Road and Baker Road, including one house on Baker Road and one on Rayvid Way. All seven houses were built by members of the locally prominent Paine family in the mid-19th century, and are predominantly Greek Revival in their styling.The district was listed on the National Register of Historic Places in 1999.