[4] In 1661, the town was the location of one of the hideouts of the "Regicides"—three of the judges who signed the death warrant for King Charles I of England.

The ruins of their hideout can be found on the nearby West Rock ridge, which runs along the town's eastern border.

Thomas Darling (1720–1789), a tutor at Yale College and later an entrepreneur in New Haven, moved to town in 1774.

His home is now the Darling House Museum, operated by the Amity & Woodbridge Historical Society.

[5] The original farms of Woodbridge were located in the area of the West River Valley known as The Flats.

Following the onset of the 2020 George Floyd protests, Woodbridge and other affluent towns in Connecticut have faced criticism from certain civic organizations alleging the practice of exclusionary zoning.

[7][8] The Open Communities Alliance voiced disappointment regarding the scale of the change,[8] and filed a lawsuit alleging Woodbridge was in violation of Connecticut's Zoning Enabling Act and Fair Housing Act in August 2022 in a case which has attracted statewide attention.

[12] Cardozo served two terms as Deputy Selectman to former First Selectwoman Beth Heller and was appointed as Ordinance Chairman.

The Board of Selectmen elected Sheehy First Selectman by a 3 to 2 vote, along party lines, to replace Amey Marella (Republican), who stepped down to accept a job as Deputy Commissioner of the Connecticut Department of Environmental Protection.

Woodbridge also shares the Amity Regional High School with the neighboring towns of Bethany and Orange.

Woodbridge is home to Ezra Academy, a regional Jewish day school whose students reside in 21 towns throughout New Haven and Fairfield counties.

Woodbridge is informally divided into two distinct parts: central Woodbridge, which occupies the western hilly side of town; and the area known as The Flats, which occupies the eastern slice of town, bordering West Rock and the New Haven neighborhood of Westville.

[27] The town has an extensive system of preserved hiking trails open to the public, notably the 93-acre (380,000 m2) Alice Newton Street Memorial Park and the 22-acre (89,000 m2) Wepawaug Falls area.