Dr. Andrew Castle House

Amity High School is a regional public high school located in Woodbridge, Connecticut, United States. It provides high school education (grades 9–12) for the children in the towns of Woodbridge, Orange, and Bethany (which together form Regional District #5 for the purpose of secondary education). The name Amity is derived from both the colonial history of Woodbridge as well as the "friendship" demonstrated among the three founding towns in arranging for a communal educational program. In 2014, Newsweek magazine ranked Amity 112th among public high schools nationally, higher than any other high school in the state.During the 2014–2015 academic year, the school district spent $17,091 per pupil, as compared to the state average of $16,249. Approximately 51% were residents of Orange, 29% were residents of Woodbridge and 20% were residents of Bethany. About 87.3% of the students were white, 7.9% were Asian-American, 2.6% were Hispanic, 2.0% were African-American and 0.2% were American Indian. There were approximately 122 teachers and 1,636 students, for an average student-teacher ratio of 13.4:1, although the actual ratio varies by course and teacher contract.

The James Alexis Darling House is a historic house at 1932 Litchfield Turnpike (Connecticut Route 69) in Woodbridge, Connecticut. Built in 1842 for a grandson of Thomas Darling (whose house stands nearby), it is a good example of a rural Greek Revival farmhouse. Although built with the latest exterior styling, its construction style harkens back to 18th-century building practices. James Alexis Darling worked in the family mercantile business and moved to Woodbridge to oversee his grandfather's farm.The house was listed on the National Register of Historic Places in 2020.

The New England Cement Company Kiln and Quarry are a historic archaeological industrial site in Woodbridge, Connecticut. Located on and near a ridge paralleling Litchfield Turnpike, the site includes two components: a stone kiln used for processing cement, and a hand-dug quarry from which limestone used in the cement manufacture was taken. The site has an industrial history dating to 1847; the kiln, which survives in deteriorated condition, dates to 1874.A modern account of the demise of this business states there is "evidence of a nineteenth century scam" in which investors lost money. According to a 2013 article in The New York Times,"The concept was simple, toss local rock into the large stone furnace and wait until it melts. Then out comes fine cement. In this case the local bedrock proved unusable and produced an inferior product. Speculation is that the first batch was hauled into New Haven and dumped into the harbor more than 100 years ago." However this is contradicted by a more contemporaneous account by U.S. Congressman Nehemiah D. Sperry as recounted in a local newspaper's coverage of his 1895 trip through this area where he grew up. Sperry said, "And here we are opposite the dam. Just over there on the hillside are the ruins of the old cement kiln, where twenty-five years ago they made cement from the rocks that are so abundant around it. It was good cement, but the business failed and was killed because cement was a cheap article and because it took off all the profits to cart the stuff to New Haven. Perhaps some day an electric road will come by here and then the business might be profitably worked."The site was listed on the National Register of Historic Places in 2001.

The Darling House Museum is a historic house museum at 1907 Litchfield Turnpike in Woodbridge, Connecticut, and is owned and operated by the Amity & Woodbridge Historical Society. The house is open by appointment and during special events. In the early 1770s, Thomas Darling hired Abiel Gray of West Hartford, Connecticut, to build a new home in Amity Parish, outside of New Haven. Gray took two years (1772–1774) to finish the project. The house has a gambrel roof, is built on a central hall plan and has some unusual features. Paneling and woodwork in the hallway and front rooms are richly detailed under 9-foot, 3-inch ceilings. The influence of 18th-century New York is suggested by the imported tiles of Biblical scenes over one fireplace.Much of the furniture and many items in the home were owned by the Darling family, which owned the house and surrounding land until 1973, when the property was sold to the town of Woodbridge and the Amity & Woodbridge Historical Society began caring for the structure. The property includes a large 18th-century barn, a 19th-century horse barn, a carriage shed, a chicken coop, a pig house, and a 19th-century privy. The town maintains several fields near the house, and some easy walking trails skirt the base of West Rock. The Society has a large collection of farm implements on display in the horse barn. Quilts, linens, and period clothing are also displayed in the house.

Woodbridge is a town in New Haven County, Connecticut, United States. The town is part of the South Central Connecticut Planning Region. The population was 9,087 at the 2020 census. The town center is listed on the National Register of Historic Places as Woodbridge Green Historic District. Woodbridge is part of the Amity Regional School District #5, rated the #1 school district in New Haven County and the 10th best school district in CT by Niche in 2021. As of 2019 Woodbridge has the 7th highest median household income in CT.

The Flats is a neighborhood located in the southeastern end of Woodbridge, Connecticut, in the West River valley area that runs between the hilly western part of town and the rock formation known as West Rock. The West River valley continues into the city of New Haven. The Flats is bounded on the northeast by West Rock Ridge, on the south by the Amity neighborhood of New Haven, and on the northwest by an incline in elevation above which lies the highlands of Woodbridge. This region was called “Shushuck” by Native Americans. The Flats is Woodbridge's main commercial section, with mixed-use residential, recreational and retail zoning. CT Route 63 and CT Route 69 are the primary roads in this neighborhood, which form major north–south arterials between New Haven and northern towns like Bethany and the Naugatuck River Valley region beyond. CT Route 15/The Wilbur Cross Parkway runs east-west through The Flats to intersect with CT-63 and CT-69.

The Woodbridge Green Historic District is a historic district encompassing the historic town center of Woodbridge, Connecticut. It is located in the block bounded on the south by Center Road (Route 114), on the east by Newton Road, and on the north and west by Meetinghouse Lane. The center is a good example of early 20th-century town planning, with good examples of Colonial and Classical Revival architecture. The district was added to the National Register of Historic Places in 2003.

The Bi-Cultural Hebrew Academy of Connecticut is an independent Jewish K-12 school located in Stamford, Connecticut. The Jewish High School of Connecticut (JHSC) in Stamford, in the fall of 2018, merged with the Bi-Cultural Day School to become the Upper School for the Bi-Cultural Hebrew Academy of Connecticut.

Regicides Trail is a Blue-Blazed hiking trail, about 7 miles (11 km) long, roughly following the edge of a diabase, or traprock, cliff northwest of New Haven, Connecticut. It is named for two regicides, Edward Whalley and his son-in-law William Goffe, who signed the death warrant of King Charles I of England. Upon the restoration of Charles II to the throne and the persecution of the regicides, the pair hid in Judges Cave near the south end of the trail in 1660. The Regicides is widely known to be one of the most technical trails within the CT Blue-Blazed trail system.

West Rock Ridge State Park is a public recreation area located in New Haven, Hamden, and Woodbridge, Connecticut. The state park is named for the 400-to-700-foot (120 to 210 m) trap rock West Rock Ridge, which is part of the Metacomet Ridge extending from Long Island Sound to the Vermont border. The park's 7 miles (11 km) of open west-facing cliffs offer vistas encompassing Metropolitan New Haven and suburban towns to the west. The park includes Judges Cave, a colonial era historic site; Lake Wintergreen; and the 7-mile (11 km) Regicides Trail, part of the Connecticut Forest and Park Association's Blue Trail system. The park is part of a larger area of protected open space including state, municipal, and non-profit owned land.

The Congregation B'nai Jacob is a Conservative synagogue in Woodbridge, Connecticut.

WYBC-FM (94.3 MHz) is an urban adult contemporary radio station, licensed to New Haven, Connecticut. The station's studios are located on the campus of Yale University. The station is owned by Yale Broadcasting Company and operated through a local marketing agreement (LMA) with Connoisseur Media as of May 10, 2013. Through the LMA, most of WYBC-FM's programming originates from Connoisseur's facilities located on Wheelers Farms Road in Milford. The station's transmitter is located in West Rock Ridge State Park.