Broomstones Curling Club

The Old Connecticut Path was the Native American trail that led westward from the area of Massachusetts Bay to the Connecticut River Valley, the first of the North American trails that led west from the settlements close to the Atlantic seacoast, towards the interior. The earliest colonists of Massachusetts Bay Colony used it, and rendered it wider by driving cattle along it. The old route is still followed, for part of its length, by Massachusetts Route 9 and Massachusetts Route 126.

The Vokes Theatre, also known as Beatrice Herford's Vokes Theatre, is a 1904 miniature of a London theatre in Wayland, Massachusetts built by and named for Beatrice Herford. The theatre is located on the estate of Herford and her husband, Sidney Hayward.

Reeves Tavern is a historic colonial tavern (now a private residence) in Wayland, Massachusetts. Built in 1762–63, it is one of the town's best preserved examples of an early tavern. It was listed on the National Register of Historic Places in 2016.

The Robert Jenison House is a historic house at 1 Frost Road in Natick, Massachusetts. It is a 2+1⁄2-story wood-frame house, five bays wide, with a side-gable roof, large central chimney, and clapboard siding. The house was built c. 1738 by Robert Jenison. It is one of the town's oldest buildings, and its builder is known to have built a number of other houses in Sudbury and Sherborn. The house was originally part of a 200 acre tract of land that was sold by the Natick Indians despite protests from John Eliot. There is an outbuilding on the property that is marked as the site where Vice President Henry Wilson learned to make shoes.The house was added to the National Register of Historic Places in 1978, where it is listed at 470 Winter Street.

The Rivers School is an independent, coeducational preparatory school in Weston, Massachusetts.

The Noyes-Parris House is a historic First Period house located in Wayland, Massachusetts.

The Samuel Train House is a historic house in Weston, Massachusetts. Built about 1738, it is a good example of a mid-18th century colonial house. It was home to successive generations of Samuel Trains, who were all active in local politics and the state militia. The house was added to the National Register of Historic Places in 1976. It is used as office space for the Rivers School, whose main campus is located across the street.

Pope St. John XXIII National Seminary (formerly Blessed John XXIII National Seminary) is a Roman Catholic seminary in Weston, Massachusetts. It offers a graduate-level program designed for priesthood candidates aged 30 and above, often called "second-career vocations" or "delayed vocations".Founded by Boston Archbishop Richard Cardinal Cushing in 1964, the seminary was chartered by the Commonwealth of Massachusetts in 1972 and became accredited by the Association of Theological Schools in 1983. It awards graduates the M. Div. degree.

Cochituate (; koh-CHIT-choo-it) is a census-designated place (CDP) in the town of Wayland in Middlesex County, Massachusetts, United States. The population was 6,927 at the 2020 census, out of 13,943 in the entire town of Wayland.

Regis College is a private, non-profit university in Weston, Massachusetts, United States. It was founded in 1927 by the Sisters of St. Joseph of Boston. The university offers undergraduate, graduate, and professional studies degree and certificate programs via on campus, fully online, and hybrid formats. Inspired by the social justice values of the Sisters of St. Joseph of Boston, Regis engages with service initiatives within the local community and around the world.

The Wayland Center Historic District encompasses the predominantly 19th-century village center of Wayland, Massachusetts. Located at the junction of United States Route 20 and Cochituate Road (Massachusetts Route 27), it includes fifteen well-preserved 19th-century buildings that form one of the best-preserved village centers of that period near Boston. It was added to the National Register of Historic Places in 1974.